(3Z,7E)-homofarnesylic acid | 80183-39-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3Z,7E)-homofarnesylic acid
• 英文别名: (3Z,7E)-4,8,12-trimethyltrideca-3,7,11-trienoic acid
• CAS: 80183-39-7
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: FCINNSNPGOGNMQ-PVMFERMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3Z,7E)-homofarnesylic acid 、 氢化铝锂 以93%的产率得到
  参考文献：
  名称：

  VLAD, P. F.;UNGUR, N. D.;PERUTSKIJ, V. B., XIMIYA GETEROTSIKL. SOED.,(1990) N, S. 896-901

  摘要：

  DOI：
• 作为产物：
  描述：

  反式,反式-金合欢醇 在 乙二醇二甲醚溴化镍 、 锰 、 新铜试剂 、 三乙胺 、 magnesium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 (3Z,7E)-homofarnesylic acid 、 (3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienoic acid
  参考文献：
  名称：

  Ligand-Controlled Regiodivergent Ni-Catalyzed Reductive Carboxylation of Allyl Esters with CO₂

  摘要：

  A novel Ni-catalyzed regiodivergent reductive carboxylation of allyl esters with CO2 has been developed. This mild, user-friendly, and operationally simple method is characterized by an exquisite selectivity profile that is dictated by the ligand backbone.

  DOI：

  10.1021/ja509077a

文献信息

• PROCESS FOR THE PREPARATION OF UNSATURATED CARBOXYLIC ACIDS BY CARBONYLATION OF ALLYL ALCOHOLS AND THEIR ACYLATION PRODUCTS
  申请人：BASF SE

  公开号：US20200055834A1

  公开（公告）日：2020-02-20

  The present invention relates to a process for carbonylating allyl alcohols at low temperature, low pressure and/or low catalyst loading. In an alternative embodiment, an acylation product of the allyl alcohol is used for the carbonylation. The present invention likewise relates to the preparation of conversion products of these carbonylation products and specifically of (−)-ambrox.

  本发明涉及一种在低温、低压和/或低催化剂负载下对烯丙醇进行羰基化的过程。在另一实施方式中，烯丙醇的酰化产物被用于羰基化。本发明还涉及制备这些羰基化产物的转化产物，特别是(−)-龙涎香。
• Palladium‐Catalyzed Low Pressure Carbonylation of Allylic Alcohols by Catalytic Anhydride Activation
  作者：Mathias Schelwies、Rocco Paciello、Ralf Pelzer、Wolfgang Siegel、Michael Breuer

  DOI：10.1002/chem.202005324

  日期：2021.6.25

  A direct carbonylation of allylic alcohols has been realized for the first time with high catalyst activity at low pressure of CO (10 bar). The procedure is described in detail for the carbonylation of E-nerolidol, an important step in a new BASF-route to (−)-ambrox. Key to high activities in the allylic alcohol carbonylation is the finding that catalytic amounts of carboxylic anhydride activate the

  首次实现了烯丙醇的直接羰基化，在低压 CO（10 巴）下具有高催化剂活性。详细描述了E-橙花醇羰基化的过程，这是巴斯夫新途径（-）-氨溴索中的重要步骤。烯丙醇羰基化中高活性的关键是发现催化量的羧酸酐活化底物并在反应条件下用一氧化碳不断再生。确定的反应条件也可转移到其他底物。
• [EN] HYDROCARBONYLATION OR METHOXYCARBONYLATION OF 1,3-DIENE DERIVATIVES WITH PALLADIUM COMPLEX<br/>[FR] HYDROCARBONYLATION OU MÉTHOXYCARBONYLATION DE DÉRIVÉS 1,3-DIÈNE AVEC COMPLEXE DE PALLADIUM
  申请人：FIRMENICH & CIE

  公开号：WO2014079691A1

  公开（公告）日：2014-05-30

  The present invention concerns a process of carbonylation of poly-unsaturated diene with high selectivity for the preparation of a β,γ- unsaturated carboxylic acid or ester in the presence of water or alcohol and catalyzed by [PdCl2P2] complex wherein P2 is two mono or one bidendate phosphine ligand.

  本发明涉及一种在水或醇的存在下，由[PdCl2P2]复合物催化的，具有高选择性的聚不饱和二烯的羰基化过程，用于制备β,γ-不饱和羧酸或酯。其中P2是两个单磷或一个双齿膦配体。
• CYCLIZATION OF E,E-HOMOFARNESIC ACID AND ITS RELATED COMPOUNDS
  作者：Akira Saito、Hajime Matsushita、Hajime Kaneko

  DOI：10.1246/cl.1984.591

  日期：1984.4.5

  Acid-catalyzed cyclization of homofarnesic acid was examined in detail. E,E- and Z,E-homofarnesic acid in dichloromethane cyclyzed by catalysis of boron trifluoride etherate at −20°C to afford trans-anti-trans and trans-syn-cis norambreinolide in 38% and 52% yield respectively. Cyclization mechanism was discussed.

  研究人员详细考察了酸催化环化高法萘酸的过程。在三氟化硼醚化物的催化下，二氯甲烷中的 E,E- 和 Z,E- 卤马尼酸在-20°C 下发生环化反应，生成反式-反式和反式-顺式去甲卤马尿苷内酯，收率分别为 38% 和 52%。对环化机理进行了讨论。
• [EN] METHOD FOR THE ISOMERIZATION OF A 3-(Z)-UNSATURATED CARBOXYLIC ACID TO THE 3-(E)-ISOMER<br/>[FR] PROCÉDÉ D'ISOMÉRISATION D'UN ACIDE CARBOXYLIQUE 3-(Z)-INSATURÉ EN ISOMÈRE 3-(E)
  申请人：BASF SE

  公开号：WO2019158611A1

  公开（公告）日：2019-08-22

  The present invention relates to a method for isomerizing a 3-(Z)-unsaturated carboxylic acid of the formula l-Z or a salt thereof, wherein R2 is C1-C24-alkyl, C2-C24-alkenylhaving 1, 2, 3 or more than 3 C-C double bonds, unsubstituted or substituted C5-C12-cycloalkyl, or unsubstituted or substituted aryl; R1 is hydrogen or has one of the definitions specified for R2; with the proviso that R2 has a higher priority than R1 in accordance with lUPAC; to give a 3-(E)-unsaturated carboxylic acid of the formula I-E or a salt thereof, wherein the isomerization of the compound of the formula l-Z is effected in the presence of an anhydride of an organic acid and a base or in the presence of a ketene of formula CR11R12C(0), wherein R11 and R12 are as defined in the claims and in the specification and a base. In particular, the present invention relates to a method for preparing compositions with increased content of (3E, 7E)-homofarnesylic acid starting from compositions comprising (3Z,7E)- and (3E, 7E)-homofarnesylic acid.

  本发明涉及一种异构化3-(Z)-不饱和羧酸的方法，其化学式为l-Z或其盐，其中R2为C1-C24烷基，C2-C24烯基，具有1、2、3或多于3个C-C双键，未取代或取代的C5-C12环烷基或未取代或取代的芳基；R1为氢或具有R2指定的定义之一；在符合lUPAC的前提下，R2优先级高于R1，从而得到3-(E)-不饱和羧酸的化学式I-E或其盐。其中，在存在有机酸酐和碱或存在化学式为CR11R12C(0)的酮（其中R11和R12在权利要求和说明书中定义）和碱的情况下，对化合物l-Z进行异构化。特别地，本发明涉及一种制备含有增加的(3E,7E)-同型法尼酸的组合物的方法，其起始物为含有(3Z,7E)-和(3E,7E)-同型法尼酸的组合物。