abienol acetate | 119987-18-7

• 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: abienol acetate
• 英文别名: [(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-[(2Z)-3-methylpenta-2,4-dienyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl] acetate
• CAS: 119987-18-7
• 化学式: C₂₂H₃₆O₂
• 分子量: 332.527
• InChiKey: UYMUJGVWTFGNHE-YJKYYOEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  abienol acetate 、 氢化铝锂 生成 (+)-顺式-枞醇
  参考文献：
  名称：

  COSTE-MANIERE, I. C.;ZAHRA, J. P.;WAEGELL, B., TETRAHEDRON LETT., 29,(1988) N 9, 1017-1020

  摘要：

  DOI：
• 作为产物：
  描述：

  香紫苏醇 在 palladium diacetate N,N-二甲基苯胺 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 生成 abienol acetate
  参考文献：
  名称：

  Zahra, Jean-Pierre; Chauvet, Frederic; Coste-Maniere, Ivan, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 10,11, p. 1001 - 1024

  摘要：

  DOI：

文献信息

• Synthesis of ambergris fragrance chemicals from sclareol, involving palladium catalysed key steps
  作者：I.C. Coste-Manière、J.P. Zahra、B. Waegell

  DOI：10.1016/0040-4039(88)85323-1

  日期：1988.1

  Ambraoxide, Ambrox ®, methylambraoxide and ambracetal are synthetised via key steps involving respectively a palladium acetate catalysed elimination and a PdCl2(CH3CN)2 catalysed isomerisation of the mixture of sclareol and episclareol acetates.

  通过关键步骤合成Ambraoxide，Ambrox®，甲基Ambraoxide和ambracetal，这些关键步骤分别包括醋酸钯催化的香紫苏醇和醋酸表紫醇的混合物的乙酸钯催化的消除和PdCl 2（CH 3 CN）2催化的异构化。
• [EN] METHOD FOR THE CONVERSION OF ABIENOL TO SCLAREDIOL<br/>[FR] PROCÉDÉ POUR LA CONVERSION D'ABIÉNOL EN SCLAREDIOL
  申请人：GIVAUDAN SA

  公开号：WO2016146769A1

  公开（公告）日：2016-09-22

  A method of selective conversion of Abienol, represented by formula 1, to Sclareodial, represented by formula 2 by ozonolysis and subsequent reduction. The ozonolysis is carried out at temperatures above -60 °C, preferably in nonhalogenated solvents. R is selected from H, acetals, aminals, optionally substituted alkyl groups, such as benzyl group, carboxylates such as acetates or formates, carbonates such as methyl or ethyl carbonates, carbamates, and any protecting group which can be attached to 1 and cleaved from 2, R' is selected from CH=CH2, an alkyl moiety with C2-C20, e.g. CH2-CH3, or a cycloalkyl or polycycloalkyl moiety with C3-C20, e.g. cyclopropyl, optionally alkylated, respectively, and the wavy bond is depicting an unspecified configuration of the adjacent double bond between C2 and C3.

  一种通过臭氧化和随后还原选择性转化Abienol（化学式1）为Sclareodial（化学式2）的方法。臭氧化在-60°C以上的温度下进行，最好在非卤代溶剂中进行。R可以选择为H、缩醛、缩胺、可选的取代烷基，如苄基、羧酸酯，如乙酸盐或甲酸盐、碳酸酯，如甲基或乙基碳酸酯、氨基甲酸酯，以及可以附加到1并从2中断裂的任何保护基团，R'可以选择为CH=CH2、具有C2-C20的烷基残基，例如 -CH3，或具有C3-C20的环烷基或多环烷基残基，例如环丙基，分别进行烷基化，波浪线表示C2和C3之间相邻双键的未指定构型。
• Method for the conversion of Abienol to Sclarediol
  申请人：GIVAUDAN SA

  公开号：US10633314B2

  公开（公告）日：2020-04-28

  A method of selective conversion of Abienol, represented by formula 1, to Sclareodiol, represented by formula 2 by ozonolysis and subsequent reduction. The ozonolysis is carried out at temperatures above −60° C., preferably in nonhalogenated solvents. R is selected from H, acetals, aminals, optionally substituted alkyl groups, such as benzyl group, carboxylates such as acetates or formates, carbonates such as methyl or ethyl carbonates, carbamates, and any protecting group which can be attached to 1 and cleaved from 2, R′ is selected from CH═CH2, an alkyl moiety with C2-C20, e.g. CH2—CH3, or a cycloalkyl or polycycloalkyl moiety with C3-C20, e.g. cyclopropyl, optionally alkylated, respectively, and the wavy bond is depicting an unspecified configuration of the adjacent double bond between C2 and C3.

  一种将式 1 所代表的 Abienol 选择性转化为式 2 所代表的 Sclareodiol 的方法 通过臭氧分解和随后的还原。臭氧分解在-60°C 以上的温度下进行，最好在非卤化溶剂中进行。R 选自 H、乙醛、氨基、任选取代的烷基（如苄基）、羧酸盐（如乙酸盐或甲酸盐）、碳酸 盐（如碳酸甲酯或碳酸乙酯）、氨基甲酸酯以及任何可连接到 1 并从 2 中裂解的保护基，R′ 选自 CH═CH2、C2-C20 的烷基（如 -CH3）或环芳基。例如 - ，或 C3-C20 的环烷基或多环烷基，例如环丙基，可选烷基化，波浪键表示 C2 和 C3 之间相邻双键的未指定构型。
• METHOD FOR THE CONVERSION OF ABIENOL TO SCLAREDIOL
  申请人：Givaudan S.A.

  公开号：EP3271343B1

  公开（公告）日：2019-10-09
• Method for the Conversion of Abienol to Sclarediol
  申请人：GIVAUDAN SA

  公开号：US20180072644A1

  公开（公告）日：2018-03-15

  A method of selective conversion of Abienol, represented by formula 1, to Sclareodiol, represented by formula 2 by ozonolysis and subsequent reduction. The ozonolysis is carried out at temperatures above −60° C., preferably in nonhalogenated solvents. R is selected from H, acetals, aminals, optionally substituted alkyl groups, such as benzyl group, carboxylates such as acetates or formates, carbonates such as methyl or ethyl carbonates, carbamates, and any protecting group which can be attached to 1 and cleaved from 2, R′ is selected from CH═CH 2 , an alkyl moiety with C2-C20, e.g. CH 2 —CH 3 , or a cycloalkyl or polycycloalkyl moiety with C3-C20, e.g. cyclopropyl, optionally alkylated, respectively, and the wavy bond is depicting an unspecified configuration of the adjacent double bond between C2 and C3.