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    • 1. 发明授权
    • Epimerization of trans chrysanthemates
    • 反式菊花异构化
    • US4447637A
    • 1984-05-08
    • US347278
    • 1982-02-09
    • Jacques MartelJean BuendiaJeanine Nierat
    • Jacques MartelJean BuendiaJeanine Nierat
    • C07C69/747C07C51/353C07C51/487C07C61/04C07C61/37C07C67/333C07C69/74C07C61/18
    • C07C61/37C07C51/353C07C51/487
    • A novel process for the epimerization of alkyl trans chrysanthemates comprising reacting at a low temperature in an anhydrous organic solvent an alkyl trans chrysanthemate of the formula ##STR1## of the 1S, trans or 1R, trans configuration wherein R is alkyl of 1 to 6 carbon atoms with a strong alkali metal base to obtain a compound of the formula ##STR2## wherein R has the above definition and M is an alkali metal, reacting the latter compound with a reactant of the formulaY--Awherein A is selected from the group consisting of chlorine, bromine, iodine and anion derived from a hydrogen acid and Y is an organic radical capable of forming a ketal of a ketene to obtain a compound of the formula ##STR3## reacting the latter at a low temperature in an anhydrous organic solvent with a proton donor to obtain a mixture of the corresponding alkyl cis chrysanthemate and alkyl trans chrysanthemate and recovering the cis chrysanthemic acid of the formula ##STR4## with the 1R, cis or 1S, cis configuration.
    • 一种用于烷基反式菊氨酸差向异构化的新方法,其包括在低温下在无水有机溶剂中反应1S,反式或1R,反式构型的式II的烷基反式菊酯,其中R是1至6的烷基 具有强碱金属碱的碳原子以得到式III的化合物,其中R具有上述定义,M是碱金属,使后一化合物与式YA的反应物反应,其中A选自 由氯,溴,碘和由氢酸衍生的阴离子组成,Y是能够形成乙烯酮缩酮的有机基团,得到下式的化合物,其中IV在低温下与无水有机物 溶剂与质子供体反应,得到相应的顺式菊酸菊酯和反式菊酸酯的混合物,并用1R,顺式或1S的方法回收式Ⅰ的顺式菊酸, 顺式配置。
    • 2. 发明授权
    • Perfumant cyclopropane-carboxylic acid derivatives
    • 香料环丙烷 - 羧酸衍生物
    • US4431576A
    • 1984-02-14
    • US343348
    • 1982-01-27
    • Jacques MartelJean BuendiaFrancois Nezot
    • Jacques MartelJean BuendiaFrancois Nezot
    • C07C69/747A01N53/06A01N53/10A61K8/37A61Q13/00C07D307/54C07D307/58C07D333/24C07D333/32C11B9/00A61K7/46
    • C11B9/0092C07D307/54C07D333/24C11B9/003C11B9/0076
    • A compound in all its possible isomeric forms and mixtures thereof of the formula ##STR1## wherein R is selected from the group consisting of (a) alkyl of 1 to 12 carbon atoms optionally substituted with cycloalkyl or cycloalkenyl of 3 to 6 carbon atoms or a hydrocarbon chain of 2 to 8 carbon atoms optionally interrupted by an oxygen or ketone, (b) alkenyl and alkynyl of 3 to 8 carbon atoms, (c) cycloalkyl of 3 to 12 carbon atoms optionally containing at least one double bond and substituted with at least one alkyl and (d) aralkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and --CF.sub.3 and R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, --CHO, --COAlK.sub.1, --COOAlK.sub.2 and --CN, at least one being hydrogen, AlK.sub.1 and AlK.sub.2 are alkyl of 1 to 8 carbon atoms and R.sub.1 and R.sub.2 taken together with the carbon atom to which they are attached form the group ##STR2## and X is selected from the group consisting of sulfur, oxygen and imino joined to the 1-carbon atom with a double bond with the proviso that the double bond has the E geometry when R.sub.1 or R.sub.2 are --CHO, --COAlK.sub.1, --COOAlK.sub.2 or ##STR3## and their preparation and odorant compositions containing at least one compound of formula I as a perfume agent.
    • 化合物,其全部可能的异构形式及其混合物,其中R选自(a)任选被3至6个碳原子的环烷基或环烯基取代的1至12个碳原子的烷基或 2至8个碳原子的烃链任选被氧或酮中断,(b)3至8个碳原子的烯基和炔基,(c)3至12个碳原子的环烷基,任选地含有至少一个双键并被 至少一个烷基和(d)7-12个碳原子的芳烷基,任选被至少一个1-4个碳原子的烷基,1-4个碳原子的烷氧基,卤素和-CF 3和R 1和 R2分别选自氢,-CHO,-COAlK1,-COOAlK2和-CN,至少一个为氢,AlK1和AlK2为1至8个碳原子的烷基,R1和R2与碳原子一起 它们所连接的组由和X选自硫,氧和亚氨基与具有双键的1-碳原子连接,条件是当R1或R2为-CHO,-COAlK1, - COOAlK2或及其制备和加味剂组合物,其含有至少一种式I化合物作为预浸剂。
    • 3. 发明授权
    • Novel cyclopropane carboxylate esters
    • 新型环丙烷羧酸酯
    • US4406829A
    • 1983-09-27
    • US318445
    • 1981-11-05
    • Jacques MartelJean BuendiaFrancois Nezot
    • Jacques MartelJean BuendiaFrancois Nezot
    • C07C69/747A61K8/37A61Q13/00C11B9/00C07C69/743
    • C11B9/0026
    • Novel esters of all possible isomers and mixtures thereof of compounds of the formula ##STR1## wherein n is a number of 2,3 or 4 and R is selected from the group consisting of (a) alkyl of 1 to 12 carbon atoms optionally substituted with a member of the group consisting of cycloalkyl of 3 to 6 carbon atoms and a hydrocarbon chain of 2 to 8 carbon atoms optionally interrupted by an oxygen atom or a ketone group, (b) alkenyl and alkynyl of 3 to 8 carbon atoms, (c) cycloalkyl of 3 to 12 carbon atoms optionally containing at least one double bond and optionally substituted with at least one alkyl of 1 to 5 carbon atoms and (d) aralkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and --CF.sub.3 having perfume and insecticidal properties.
    • 所有可能的异构体的新型酯及其下式化合物的混合物,其中n是2,3或4的数,R选自(a)任选取代的(a)1至12个碳原子的烷基 与碳原子数为3〜6的环烷基和碳原子数为2〜8的烃链任选被氧原子或酮基中断的基团,(b)碳原子数为3〜8的烯基和炔基,( c)3至12个碳原子的环烷基,任选地含有至少一个双键并且任选被至少一个1至5个碳原子的烷基取代,和(d)7-12个碳原子的芳烷基,任选被至少一个 由1至4个碳原子的烷基,1至4个碳原子的烷氧基,卤素和具有香料和杀虫性能的-CF 3组成的组。
    • 4. 发明授权
    • Cyclopropanecarboxylic acids and esters
    • US3997586A
    • 1976-12-14
    • US395146
    • 1973-09-07
    • Jacques MartelChanh HuynhJean Buendia
    • Jacques MartelChanh HuynhJean Buendia
    • C07C317/14C07D307/54C07D309/04C07C69/14C07C61/12C07D307/26
    • C07C317/14C07D307/54C07D309/04
    • Novel cyclopropanecarboxylic acids and esters of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are selected from the group consisting of hydrogen, alkyl, aralkyl, aryl, alkenyl non-conjugated with the cyclopropane ring, alkenyl non-conjugated with the cyclopropane ring, cycloalkyl, cycloalkenyl and heterocyclic; R is selected from the group consisting of OH and OR' in which R' is selected from the group consisting of lower alkyl which may be substituted, benzyl which may be substituted on the phenyl or methylene portion, N-methylene-dicarboximide, (5-benzyl-furyl-3) methyl, and a cyclopentene of the formula ##STR2## WHEREIN R" is selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic; A is a bivalent alkyl radical selected from the group consisting of ##STR3## WHEREIN R.sub.1 is selected from the group consisting of hydrogen and lower alkyl, R.sub.2 and R.sub.3 are selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic and taken together with the carbon atom to which they are attached form a ring selected from the group consisting of carbon homo rings and unsaturated carbon homo rings of 3 to 7 carbon atoms and heterocyclic rings which may be substituted with lower alkyl or lower alkoxy and R.sub.2 and R.sub.3 may together form a polycyclic aromatic radical, R.sub.4 is lower alkyl, R.sub.5 is selected from the group consisting of hydrogen and lower alkyl and R.sub.4 and R.sub.5 together with the carbon atoms to which they are attached may form a saturated or unsaturated carbon homo ring or a heterocyclic ring, Y is selected from the group consisting of methylene and a saturated or unsaturated carbon chain and Y' is selected from the group consisting of methine and a saturated or unsaturated carbon chain with the proviso that when Z.sub.1 and Z.sub.2 are methyl and R.sub.1 is hydrogen, R.sub.2 is other than methyl and their preparation.
    • 5. 再颁专利
    • Cyclopentanone derivatives
    • 环戊酮衍生物
    • USRE29587E
    • 1978-03-21
    • US704846
    • 1976-07-13
    • Jacques MartelEdmond ToromanoffJean Buendia
    • Jacques MartelEdmond ToromanoffJean Buendia
    • C07C405/00
    • C07C405/00
    • Novel prostanoic acid derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 7 carbon atoms, R.sub.1 is selected from the group consisting of hydrogen and carbalkoxy of 1 to 7 alkyl carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, carboxy and carbalkoxy of 1 to 7 alkyl carbon atoms, R.sub.3 is selected from the group consisting of hydrogen and .alpha.-tetrahydropyranyl .Iadd.and at least one of R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen.Iaddend., m is 3, 4 or 5 and n is 2, 3 or 4 with the proviso that when R.sub.1 is carbalkoxy, R is alkyl of 1 to 7 carbon atoms, R.sub.2 is hydrogen and R.sub.3 is .alpha.-tetrahydropyranyl; when R.sub.2 is carbalkoxy, R is alkyl of 1 to 7 carbon atoms, R.sub.1 is hydrogen and R.sub.3 is .alpha.-tetrahydropyranyl and when R.sub.2 is carboxy, R and R.sub.1 are hydrogen and R.sub.3 is .alpha.-tetrahydropyranyl, which possess the physiological activity of prostaglandins .[. , and salts thereof when R, R.sub.1, R.sub.2 and R.sub.3 are hydrogen, with non-toxic, pharmaceutically acceptable bases.]. and their preparation.
    • 6. 发明授权
    • Prostanoic acid derivatives and therapeutic compositions
    • 前列腺酸衍生物和治疗组合物
    • US4061729A
    • 1977-12-06
    • US587558
    • 1975-06-17
    • Jacques MartelJean BuendiaMichel Vivat
    • Jacques MartelJean BuendiaMichel Vivat
    • C07C405/00C07C177/00A61K31/19A61K31/215
    • C07C405/00
    • Novel prostanoic acid derivatives of the formula ##STR1## wherein R is hydrogen or alkyl having 1 to 4 carbon atoms, m is a whole number from 3, 4 or 5, n is a whole number from 2, 3 or 4, R' is either a linear or branched, saturated or unsaturated aliphatic hydrocarbon having 1 to 4 carbon atoms, or a saturated or mono unsaturated cyclohydrocarbon having 3 to 6 carbon atoms and A is either alkoxy having 1 to 4 carbon atoms or oxygen of a ketonic group, the dotted lines in the pentagonal ring are possible positions of a single double bond where, when A is a ketonic oxygen, the double bond is on the exterior of the ring and when A is alkoxy, the double bond is in one of the two interior positions of the ring, as well as the pharmaceutically compatible salts of mineral or organic bases when R is hydrogen in their .alpha.,.beta. or .beta.,.alpha. forms and mixtures thereof; as well as the process for their preparation, and the therapeutic compositions containing them.
    • 新颖的式(IMAGE)的前列腺酸衍生物,其中R为氢或具有1至4个碳原子的烷基,m为3,4或5的整数,n为2,3或4的整数,R'为 具有1至4个碳原子的直链或支链饱和或不饱和脂族烃,或具有3至6个碳原子的饱和或单不饱和环烃,A为具有1至4个碳原子的烷氧基或酮基氧, 五角环中的虚线是单个双键的可能位置,其中当A为酮氧时,双键位于环的外部,当A为烷氧基时,双键位于两个内部位置之一 的环,以及当R是其α,β或β,α形式及其混合物中的氢时,矿物或有机碱的药学上相容的盐; 以及它们的制备方法和含有它们的治疗组合物。
    • 8. 发明授权
    • Method of imparting a pleasant odor
    • 赋予气味的方法
    • US4521331A
    • 1985-06-04
    • US438486
    • 1982-11-02
    • Jacques MartelJean BuendiaFrancois Nezot
    • Jacques MartelJean BuendiaFrancois Nezot
    • C07C69/003A61K8/37A61Q13/00C07C67/00C07C69/007C07C253/00C07C255/17C07C255/46C07C255/57C07D207/00C07D213/79C07D213/80C07D307/54C07D307/64C07D307/68C07D333/24C07D333/32C11B9/00A61K7/16C11D3/50
    • C11B9/003C07D333/32
    • All possible isomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of alkyl of 1 to 8 carbon atoms and alkenyl of 2 to 8 carbon atoms and R is selected from the group consisting of (a) hydrogen, (b) alkyl of 1 to 12 carbon atoms and alkenyl and alkynyl of 2 to 12 carbon atoms optionally substituted with cyano, saturated or unsaturated cycloalkyl or bicycloalkyl of 3 to 12 carbon atoms also optionally substituted, and optionally interrupted by an oxygen atom or containing a keto group, (c) cycloalkyl of 3 to 12 carbon atoms optionally having at least one double bond and at least one alkyl substituent of 1 to 4 carbon atoms, (d) aryl, arylalkyl, aralkenyl and aralkynyl of 6 to 20 carbon atoms optionally substituted on the aryl ring and the alkyl, alkenyl or alkynyl being optionally interrupted with an oxygen or containing a ketone group and (e) heteroaryl, heteroaralkyl, heteroaralkenyl and heteroaralkynyl optionally substituted on the heteroaryl ring and the alkyl, alkenyl and alkynyl being optionally interrupted with an oxygen atom or having a keto group with the proviso that R is not methyl when R.sub.1 is 2-methyl-1-propenyl, useful as perfume agents.
    • 式Ⅰ化合物的所有可能的异构体形式及其混合物,其中R 1选自1至8个碳原子的烷基和2至8个碳原子的链烯基,R选自 (a)氢,(b)1至12个碳原子的烷基和2至12个碳原子的烯基和炔基,其任选被氰基,3至12个碳原子的饱和或不饱和环烷基或双环烷基取代,也可任选地被 氧原子或含有酮基,(c)任选具有至少一个双键和至少一个碳原子数为1至4的烷基取代基的碳原子数为3至12的环烷基,(d)芳基,芳基烷基,芳烯基和芳炔基 任选在芳基环上被取代的碳原子数6〜20个,烷基,链烯基或炔基任选被氧或含有酮基中断,和(e)杂芳基,杂芳烷基,杂链烯基和杂炔基任选地 在杂芳基环上被取代,并且烷基,烯基和炔基任选被氧原子中断或具有酮基,条件是当R 1是2-甲基-1-丙烯基时,R不是甲基,可用作香料剂。
    • 9. 发明授权
    • Novel cyclopropanecarboxylic acids and esters
    • US4206140A
    • 1980-06-03
    • US910695
    • 1978-05-30
    • Jacques MartelChanh HuynhJean Buendia
    • Jacques MartelChanh HuynhJean Buendia
    • B23D61/02B29C37/00C07C21/14C07C22/04C07C35/04C07C61/35C07D307/45C07D307/54C07D309/04C07D309/10C07D309/20C07C61/18C07C61/28
    • C07D307/42B23D61/02B29C37/00C07C21/14C07C22/04C07C35/045C07C61/35C07D307/54C07D309/04C07D309/10C07D309/20
    • Novel cyclopropanecarboxylic acids and esters of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are selected from the group consisting of hydrogen, alkyl, aralkyl, aryl, alkenyl non-conjugated with the cyclopropane ring, alkynyl non-conjugated with the cyclopropane ring, cycloalkyl, cycloalkenyl and heterocyclic; R is selected from the group consisting of OH and OR' in which R' is selected from the group consisting of lower alkyl which may be substituted, benzyl which may be substituted on the phenyl or methylene portion, N-methylene-dicarboximide, (5-benzyl-furyl-3) methyl, and a cyclopentene of the formula ##STR2## wherein R" is selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic; A is a bivalent alkyl radical selected from the group consisting of ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen and lower alkyl, R.sub.2 and R.sub.3 are selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic and taken together with the carbon atom to which they are attached form a ring selected from the group consisting of carbon homo rings and unsaturated carbon homo rings of 3 to 7 carbon atoms and heterocyclic rings which may be substitued with lower alkyl or lower alkoxy and R.sub.2 and R.sub.3 may together form a polycyclic aromatic radical, R.sub.4 is lower alkyl, R.sub.5 is selected from the group consisting of hydrogen and lower alkyl and R.sub.4 and R.sub.5 together with the carbon atoms to which they are attached may form a saturated or unsaturated carbon homo ring or a heterocyclic ring, Y is selected from the group consisting of methylene and a saturated or unsaturated carbon chain and Y' is selected from the group consisting of methine and a saturated or unsaturated carbon chain with the proviso that when Z.sub.1 and Z.sub.2 are methyl and R.sub.1 is hydrogen, R.sub.2 is other than methyl and their preparation.
    • 10. 发明授权
    • Cyclopropanecarboxylic acid chlorides
    • US4101574A
    • 1978-07-18
    • US749402
    • 1976-12-10
    • Jacques MartelChanh HuynhJean Buendia
    • Jacques MartelChanh HuynhJean Buendia
    • B23D61/02B29C37/00C07C21/14C07C22/04C07C35/04C07C61/35C07D307/45C07D307/54C07D309/04C07D309/20C07C61/18
    • C07D309/20B29C37/00C07C21/14C07C22/04C07C35/045C07C61/35C07D307/42C07D307/54C07D309/04
    • Novel cyclopropanecarboxylic acids and esters of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are selected from the group consisting of hydrogen, alkyl, aralkyl, aryl, alkenyl non-conjugated with the cyclopropane ring, alkynyl non-conjugated with the cyclopropane ring, cycloalkyl, cycloalkenyl and heterocyclic; R is selected from the group consisting of OH and OR' in which R' is selected from the group consisting of lower alkyl which may be substituted, benzyl which may be substituted on the phenyl or methylene portion, N-methylene-dicarboximide, (5-benzyl-furyl-3) methyl, and a cyclopentene of the formula ##STR2## WHEREIN R" is selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic; A is a bivalent alkyl radical selected from the group consisting of ##STR3## WHEREIN R.sub.1 is selected from the group consisting of hydrogen and lower alkyl, R.sub.2 and R.sub.3 are selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic and taken together with the carbon atom to which they are attached form a ring selected from the group consisting of carbon homo rings and unsaturated carbon homo rings of 3 to 7 carbon atoms and heterocyclic rings which may be substituted with lower alkyl or lower alkoxy and R.sub.2 and R.sub.3 may together form a polycyclic aromatic radical, R.sub.4 is lower alkyl, R.sub.5 is selected from the group consisting of hydrogen and lower alkyl and R.sub.4 and R.sub.5 together with the carbon atoms to which they are attached may form a saturated or unsaturated carbon homo ring or a heterocyclic ring, Y is selected from the group consisting of methylene and a saturated or unsaturated carbon chain and Y' is selected from the group consisting of methine and a saturated or unsaturated carbon chain with the proviso that when Z.sub.1 and Z.sub.2 are methyl and R.sub.1 is hydrogen, R.sub.2 is other than methyl and their preparation.