(R)-2,2,4-trimethyl-cyclohex-3-enecarboxylic acid | 13746-43-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2,2,4-trimethyl-cyclohex-3-enecarboxylic acid
• 英文别名: (R)-2,2,4-Trimethyl-cyclohex-3-encarbonsaeure；(1R)-2,2,4-trimethylcyclohex-3-ene-1-carboxylic acid
• CAS: 13746-43-5
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: LMQGITVNFNTYPJ-QMMMGPOBSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  260.1±19.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (R)-2,2,4-trimethyl-cyclohex-3-enecarboxylic acid 在 sodium hydroxide 、 sodium hypobromide 、 臭氧 作用下， 生成 (R)-5,5-dimethyl-cyclopent-3-ene-1,3-dicarboxylic acid
  参考文献：
  名称：

  Nonaka, Nippon Kagaku Zasshi, 1956, vol. 77, p. 1818,1825

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,4-三甲基环己-3-烯-1-羧酸 在 (S)-(-)- α-甲基苄胺 作用下， 以17%的产率得到(R)-2,2,4-trimethyl-cyclohex-3-enecarboxylic acid
  参考文献：
  名称：

  Synthesis of both enantiomers of cis-α-irone and cis-γ-irone, principal constituents of iris oil, via resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid

  摘要：

  The principal constituents of iris oil, (-)-cis-alpha -irone and (-)-cis-gamma -irone, and their enantiomers, were synthesized from (-)- and (+)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acids. The racemic acid was resolved by recrystallization of its salt with a chiral amine, or by enzymatic hydrolysis of the corresponding alcohol. The fragrances of (-)-(1R,SS)-cis-alpha -irone and (-)-(1R,SS)-cis-gamma -irone were superior to those of (+)-(1S,5R)-cis-alpha -irone and (+)-(1S,5R)-cis-gamma -irone. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00345-1

文献信息

• Ireland-Claisen rearrangement for the stereoselective formation of the C2C3 bond in taxanes
  作者：Philip Magnus、Nicholas Westwood

  DOI：10.1016/s0040-4039(99)00828-x

  日期：1999.6

  Ireland-Claisen rearrangement of the ester 21 gave 22 with the correct C3 stereochemistry.

  酯21的爱尔兰-克莱森重排给出具有正确的C 3立体化学的22。
• Nonaka, Nippon Kagaku Zasshi, 1956, vol. 77, p. 1818,1825
  作者：Nonaka

  DOI：——

  日期：——
• Synthesis of both enantiomers of cis-α-irone and cis-γ-irone, principal constituents of iris oil, via resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid
  作者：Takahiro Inoue、Hiromasa Kiyota、Takayuki Oritani

  DOI：10.1016/s0957-4166(00)00345-1

  日期：2000.9

  The principal constituents of iris oil, (-)-cis-alpha -irone and (-)-cis-gamma -irone, and their enantiomers, were synthesized from (-)- and (+)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acids. The racemic acid was resolved by recrystallization of its salt with a chiral amine, or by enzymatic hydrolysis of the corresponding alcohol. The fragrances of (-)-(1R,SS)-cis-alpha -irone and (-)-(1R,SS)-cis-gamma -irone were superior to those of (+)-(1S,5R)-cis-alpha -irone and (+)-(1S,5R)-cis-gamma -irone. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Kotake; Nonaka, Justus Liebigs Annalen der Chemie, 1957, vol. 607, p. 153,158
  作者：Kotake、Nonaka

  DOI：——

  日期：——