(+)-(R,R,R,E,E)-4-Ethyl-6-methylnona-2,7-diene-5-carboxylic acid | 150661-61-3

• 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,R,R,E,E)-4-Ethyl-6-methylnona-2,7-diene-5-carboxylic acid
• 英文别名: (E,2R,3R)-2-[(E,3R)-hex-4-en-3-yl]-3-methylhex-4-enoic acid
• CAS: 150661-61-3
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: VFTRDWWYISPFSB-IQLXBOHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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,R,R,E,E)-4-Ethyl-6-methylnona-2,7-diene-5-carboxylic acid 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3R,4S,5R)-4-Ethyl-5-((S)-1-iodo-ethyl)-3-((E)-(R)-1-methyl-but-2-enyl)-dihydro-furan-2-one 、 (3R,4S,5S)-4-Ethyl-5-((R)-1-iodo-ethyl)-3-((E)-(R)-1-methyl-but-2-enyl)-dihydro-furan-2-one 、 (3S,4S,5R)-3-((E)-(R)-1-Ethyl-but-2-enyl)-5-((S)-1-iodo-ethyl)-4-methyl-dihydro-furan-2-one 、 (3S,4S,5S)-3-((E)-(R)-1-Ethyl-but-2-enyl)-5-((R)-1-iodo-ethyl)-4-methyl-dihydro-furan-2-one
  参考文献：
  名称：

  Doubly Diastereoselective Iodolactonizations: Olefin and Face Selectivity in Nona-2,7-diene-5-carboxylic Acid Cyclizations

  摘要：

  Nonracemic nonadienoic acids (v) were subjected to iodolactonization conditions and, by doubly diastereoselective cyclization, delivered enantiomerically pure iodo lactones replete with up to five contiguous stereogenic centers.

  DOI：

  10.1021/jo00091a029
• 作为产物：
  描述：

  (+)-(S,E)-3-Methyl-4-hexenoic acid 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 59.08h， 生成 (+)-(R,R,R,E,E)-4-Ethyl-6-methylnona-2,7-diene-5-carboxylic acid
  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