(S)-2,2,4-trimethyl-3-cyclohexen-1-methanol | 108448-46-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2,2,4-trimethyl-3-cyclohexen-1-methanol
• 英文别名: (-)-(S)-2,2,4-trimethyl-3-cyclohexene-1-methanol；[(1S)-2,2,4-trimethylcyclohex-3-en-1-yl]methanol
• CAS: 108448-46-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: XPYOIEYPDVHLNN-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2,2,4-trimethyl-3-cyclohexen-1-methanol 在 platinum(IV) oxide N-甲基吗啉 、 甲醇 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 甲烷磺酸 、 氢气 、 锌 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醚 、 氯仿 为溶剂， 反应 17.0h， 生成 ((1R,2R,5S)-9,9-Dimethyl-8-methylene-3-oxa-bicyclo[3.3.1]non-2-yl)-acetic 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
• 作为产物：
  描述：

  (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 、 甲苯 为溶剂， 反应 120.0h， 生成 (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

文献信息

• C45- und C50-Carotinoide. 4. Mitteilung. Synthese von optisch aktiven cyclischen C20-Bausteinen und von (2R,2?R)-2,2?-Bis(4-hydroxy-3-methyl-2-butenyl)-?,?-carotin ( =C.p.450)
  作者：Heinz Wolleb、Hanspeter Pfander

  DOI：10.1002/hlca.19860690315

  日期：1986.5.7

  C45- and C50-Carotenoids: Synthesis of Optically Active Cyclic C20-Building Blocks and of (2R,2′R)-2,2′-Bis(4-hydroxy-3-methyl-2-butenyl)-β,β-carotene ( = C.p. 450)

  Ç 45 -和C 50 -Carotenoids：光学活性的环状C的合成20路技术块和（2 - [R，2' - [R）-2,2'-双（4-羟基-3-甲基-2-丁烯基） - β，β-胡萝卜素（= Cp 450）
• 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.