2-[(4R)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid | 1408287-38-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-[(4R)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid
• 英文别名: 2-[(4r)-8-Chloro-2-methyl-6-methylidene-oct-2-en-4-yloxycarbonyl]benzoic acid；2-[(4R)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yl]oxycarbonylbenzoic acid
• CAS: 1408287-38-6
• 化学式: C₁₈H₂₁ClO₄
• 分子量: 336.815
• InChiKey: YJDJGEKWFIPORN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4R)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid 在 potassium tert-butylate 、 叔丁醇 作用下， 反应 1.0h， 以55%的产率得到(R)-(-)-2-Methyl-6-methylene-2,7-octadien-4-ol
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family

  摘要：

  (R)- and (S)-Ipsdienols, components of pheromones of bark beetles of the Ips family, were synthesized with high enantiomeric purity (> 98%) from 8-chloro-2-methyl-6-methylideneoct-2-en-4-ol prepared from ethyl 3-chloropropionate via cyclopropanation according to Kulinkovich. 8-Chloro-2-methyl-6-methylideneoct-2-en-4-ol was converted into the corresponding hydrogen phthalate whose stereoisomeric salts with (R)- and (S)-1-phenylethanamines were separated by crystallization, and subsequent hydrolysis of the latter and dehydrohalogenation with potassium tert-butoxide gave targeted (R)- and (S)-ipsdienols.

  DOI：

  10.1134/s1070428012090035
• 作为产物：
  描述：

  苯酐 在 硫酸 、 水 、 三乙胺 作用下， 以 丙酮 、 苯 为溶剂， 反应 12.75h， 生成 2-[(4R)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family

  摘要：

  (R)- and (S)-Ipsdienols, components of pheromones of bark beetles of the Ips family, were synthesized with high enantiomeric purity (> 98%) from 8-chloro-2-methyl-6-methylideneoct-2-en-4-ol prepared from ethyl 3-chloropropionate via cyclopropanation according to Kulinkovich. 8-Chloro-2-methyl-6-methylideneoct-2-en-4-ol was converted into the corresponding hydrogen phthalate whose stereoisomeric salts with (R)- and (S)-1-phenylethanamines were separated by crystallization, and subsequent hydrolysis of the latter and dehydrohalogenation with potassium tert-butoxide gave targeted (R)- and (S)-ipsdienols.

  DOI：

  10.1134/s1070428012090035

文献信息

• Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family
  作者：V. N. Kovalenko、E. A. Matyushenkov

  DOI：10.1134/s1070428012090035

  日期：2012.9

  (R)- and (S)-Ipsdienols, components of pheromones of bark beetles of the Ips family, were synthesized with high enantiomeric purity (> 98%) from 8-chloro-2-methyl-6-methylideneoct-2-en-4-ol prepared from ethyl 3-chloropropionate via cyclopropanation according to Kulinkovich. 8-Chloro-2-methyl-6-methylideneoct-2-en-4-ol was converted into the corresponding hydrogen phthalate whose stereoisomeric salts with (R)- and (S)-1-phenylethanamines were separated by crystallization, and subsequent hydrolysis of the latter and dehydrohalogenation with potassium tert-butoxide gave targeted (R)- and (S)-ipsdienols.