(-)-(R,E)-3-Methyl-4-hexenoic acid | 35666-74-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (-)-(R,E)-3-Methyl-4-hexenoic acid
• 英文别名: (3R,4E)-3-Methyl-4-hexenoic acid；(E,3R)-3-methylhex-4-enoic acid
• CAS: 35666-74-1
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: VUJRXCTYDXMWKO-YUDCMIJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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,E)-3-Methyl-4-hexenoic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以88%的产率得到(-)-(R,E)-3-Methyl-4-hexen-1-ol
  参考文献：
  名称：

  Iterative enolate Claisen rearrangements: versatile route to optically pure 2,7-nonadiene-5-carboxylic acids

  摘要：

  A short, versatile, and diastereoselective method of preparing 2,7-nonadiene-5-carboxylic acids by an iterative enolate Claisen rearrangement procedure has been developed. Homochiral (E)- and (Z) secondary allylic alcohols 1-4, prepared from (S)-(-)-ethyl lactate, were esterified with acetic acid and enolized, and the resulting silyl ketene acetals were warmed to room temperature to effect [3,3]-sigmatropic rearrangement to 4-hexenoic acids 5-8. Esterification of these acids with alcohols 1-4 followed by a second enolate Claisen rearrangement delivered the targeted 2,7-nonadiene-5-carboxylic acids with high diastereoselectivity. This second [3,3]-sigmatropic rearrangement provides well-placed and potentially synthetically useful functionality and stereochemistry.

  DOI：

  10.1021/jo00069a019
• 作为产物：
  描述：

  ethyl (E)-3-methyl-4-hexenoate 在 sodium hydroxide 作用下， 生成 (-)-(R,E)-3-Methyl-4-hexenoic acid
  参考文献：
  名称：

  Asymmetric induction in the thermal reactions of allylic alcohols with N,N-dimethylacetamide dimethylacetal and triethyl orthoacetate

  摘要：

  DOI：

  10.1021/jo00796a035

文献信息

• Processes and intermediates for N-(S-3-alkylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine
  申请人：PFIZER INC.

  公开号：EP0258032B1

  公开（公告）日：1992-07-29
• Asymmetric induction in the thermal reactions of allylic alcohols with N,N-dimethylacetamide dimethylacetal and triethyl orthoacetate
  作者：Richard K. Hill、Raghovan Soman、Seiji Sawada

  DOI：10.1021/jo00796a035

  日期：1972.11
• Iterative enolate Claisen rearrangements: versatile route to optically pure 2,7-nonadiene-5-carboxylic acids
  作者：John C. McKew、Mark J. Kurth

  DOI：10.1021/jo00069a019

  日期：1993.8

  A short, versatile, and diastereoselective method of preparing 2,7-nonadiene-5-carboxylic acids by an iterative enolate Claisen rearrangement procedure has been developed. Homochiral (E)- and (Z) secondary allylic alcohols 1-4, prepared from (S)-(-)-ethyl lactate, were esterified with acetic acid and enolized, and the resulting silyl ketene acetals were warmed to room temperature to effect [3,3]-sigmatropic rearrangement to 4-hexenoic acids 5-8. Esterification of these acids with alcohols 1-4 followed by a second enolate Claisen rearrangement delivered the targeted 2,7-nonadiene-5-carboxylic acids with high diastereoselectivity. This second [3,3]-sigmatropic rearrangement provides well-placed and potentially synthetically useful functionality and stereochemistry.