2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propenal | 38049-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propenal
• 英文别名: 2-[(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl]prop-2-enal
• CAS: 38049-01-3
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: AEHSFYBTEGCGHC-FKTZTGRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 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：

  2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propenal 在 silver carbonate 作用下， 以 苯 为溶剂， 反应 12.0h， 以1.85 g的产率得到trans-p-menthanolide
  参考文献：
  名称：

  Enzyme-Mediated Preparation of Enantiomerically Pure p-Menthan- 3,9-diols and Their Use for the Synthesis of Natural p-Menthane Lactones and Ethers

  摘要：

  The diasiereoselective preparation of the p-menthane-3,9-diols (+/-)-12, (+/-)-13a, (+/-)-13b, and (+/-)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

  DOI：

  10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9
• 作为产物：
  描述：

  [1R-(1Alpha,2β,5Alpha)]-5-甲基-2-(1-甲乙烯基)环己醇乙酸酯 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 生成 2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propenal
  参考文献：
  名称：

  Tadwalkar,V.R.; Rao,A.S., Indian Journal of Chemistry, 1971, vol. 9, p. 1416 - 1417

  摘要：

  DOI：

文献信息

• Isopulegol as a Model Compound: Metalation and Substitution of an Allylic Position in the Presence of an Unprotected Hydroxy Function
  作者：Manfred Schlosser、Martina Kotthaus

  DOI：10.1002/(sici)1099-0690(199902)1999:2<459::aid-ejoc459>3.0.co;2-f

  日期：1999.2
• BAL B. S.; CHILDERS W. E. JR.; PINNICK H. W., TETRAHEDRON, 1981, 37, NO 11, 2091-2096
  作者：BAL B. S.、 CHILDERS W. E. JR.、 PINNICK H. W.

  DOI：——

  日期：——
• FRIEDRICH, DIRK;BOHLMANN, FERDINAND, TETRAHEDRON, 44,(1988) N 5, 1369-1392
  作者：FRIEDRICH, DIRK、BOHLMANN, FERDINAND

  DOI：——

  日期：——