(S,S)-3-甲基-7-辛基-7-辛烯-2-醇 | 385424-02-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S,S)-3-甲基-7-辛基-7-辛烯-2-醇
• 英文名称: (S,S)-3-methyl-7-octyl-7-octen-2-ol
• 英文别名: (2RS,3RS)-3-methyl-7-octyl-oct-7-en-2-ol；erythro-7-Hydroxy-6-methyl-2-octyl-2-octen；(2S,3S)-3-methyl-7-methylidenepentadecan-2-ol
• CAS: 385424-02-2
• 化学式: C₁₇H₃₄O
• 分子量: 254.456
• InChiKey: MDAUMHFYJOYCTH-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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,S)-3-甲基-7-辛基-7-辛烯-2-醇 在 10percent Pd/C 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成 (2S,3S,7R/S)-3,7-dimethylpentadecan-2-yl acetate
  参考文献：
  名称：

  Synthesis of the Insect Pheromone (2S,3S,7RS)-Diprionyl Acetate by Diastereoselective Protonation

  摘要：

  The insect pheromone (2S,3S,7RS)-diprionyl acetate (1) was prepared from (S,S)-2,3-dimethylcyclohexanone (2), which in turn was obtained by the 1,4-addition of lithium dimethyl-cuprate to (S)-(+)-carvone (3) and diastereoselective protonation of the resulting enolate with phenyl salicylate, followed by removal of the isopropenyl group and hydrogenation. Baeyer-Villiger rearrangement of (S,S)-2 and opening of the lactone (S,S)-8 with octyllithium provided the hydroxy ketone (S,S)-9, which was transformed into the target molecule (2S,3S,7RS)-1 by carbonyl olefination with Petasis' reagent, acylation and hydrogenation.

  DOI：

  10.1002/1099-0690(200110)2001:20<3831::aid-ejoc3831>3.0.co;2-2
• 作为产物：
  描述：

  (S,S)-6,7-dimethyl-2-oxepanone 在 叔丁基锂 作用下， 以 乙醚 、 甲苯 、 正戊烷 为溶剂， 反应 16.0h， 生成 (S,S)-3-甲基-7-辛基-7-辛烯-2-醇
  参考文献：
  名称：

  Synthesis of the Insect Pheromone (2S,3S,7RS)-Diprionyl Acetate by Diastereoselective Protonation

  摘要：

  The insect pheromone (2S,3S,7RS)-diprionyl acetate (1) was prepared from (S,S)-2,3-dimethylcyclohexanone (2), which in turn was obtained by the 1,4-addition of lithium dimethyl-cuprate to (S)-(+)-carvone (3) and diastereoselective protonation of the resulting enolate with phenyl salicylate, followed by removal of the isopropenyl group and hydrogenation. Baeyer-Villiger rearrangement of (S,S)-2 and opening of the lactone (S,S)-8 with octyllithium provided the hydroxy ketone (S,S)-9, which was transformed into the target molecule (2S,3S,7RS)-1 by carbonyl olefination with Petasis' reagent, acylation and hydrogenation.

  DOI：

  10.1002/1099-0690(200110)2001:20<3831::aid-ejoc3831>3.0.co;2-2

文献信息

• Synthesis of the Insect Pheromone (2S,3S,7RS)-Diprionyl Acetate by Diastereoselective Protonation
  作者：Sophia Ebert、Norbert Krause

  DOI：10.1002/1099-0690(200110)2001:20<3831::aid-ejoc3831>3.0.co;2-2

  日期：2001.10

  The insect pheromone (2S,3S,7RS)-diprionyl acetate (1) was prepared from (S,S)-2,3-dimethylcyclohexanone (2), which in turn was obtained by the 1,4-addition of lithium dimethyl-cuprate to (S)-(+)-carvone (3) and diastereoselective protonation of the resulting enolate with phenyl salicylate, followed by removal of the isopropenyl group and hydrogenation. Baeyer-Villiger rearrangement of (S,S)-2 and opening of the lactone (S,S)-8 with octyllithium provided the hydroxy ketone (S,S)-9, which was transformed into the target molecule (2S,3S,7RS)-1 by carbonyl olefination with Petasis' reagent, acylation and hydrogenation.