[(1S)-2,2,4-trimethylcyclohex-3-en-1-yl]methyl acetate | 127075-63-2

• 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: [(1S)-2,2,4-trimethylcyclohex-3-en-1-yl]methyl acetate
• CAS: 127075-63-2
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: BXGBHMMYDWACGQ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  [(1S)-2,2,4-trimethylcyclohex-3-en-1-yl]methyl acetate 在 PPL (SIGMA type II) from Porcine pancreas 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以57%的产率得到(S)-2,2,4-trimethyl-3-cyclohexen-1-methanol
  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
• 作为产物：
  描述：

  乙酸乙烯酯 、 (2,2,4-trimethyl-3-cyclohexen-1-yl)methanol 在 PPL (SIGMA type II) from Porcine pancreas 作用下， 以 正己烷 、 异丙醚 为溶剂， 反应 72.0h， 生成 [(1S)-2,2,4-trimethylcyclohex-3-en-1-yl]methyl acetate 、 [(1R)-2,2,4-trimethylcyclohex-3-en-1-yl]methyl acetate
  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

• HELMLINGER, DANIEL;FRATER, GEORG, HELV. CHIM. ACTA, 72,(1989) N, C. 1515-1521
  作者：HELMLINGER, DANIEL、FRATER, GEORG

  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.