ethyl (2Z,6R,1'S,5'R)-2-methyl-6-(4'-oxobicyclo[3.1.0]hex-1'-yl)hept-2-enoate | 1005411-90-4

• 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: ethyl (2Z,6R,1'S,5'R)-2-methyl-6-(4'-oxobicyclo[3.1.0]hex-1'-yl)hept-2-enoate
• 英文别名: ethyl (Z,6R)-2-methyl-6-[(1S,5R)-4-oxo-1-bicyclo[3.1.0]hexanyl]hept-2-enoate
• CAS: 1005411-90-4
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: IYYYVEKNKROOEH-KPQIZHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2Z,6R,1'S,5'R)-2-methyl-6-(4'-oxobicyclo[3.1.0]hex-1'-yl)hept-2-enoate 、 甲基三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以43%的产率得到ethyl (2Z,6R,1'S,5'S)-2-methyl-6-(4'-methylidenebicyclo[3.1.0]hex-1'yl)hept-2-enoate
  参考文献：
  名称：

  臭虫Erysarcoris lewisi（Distant），（2 Z，6 R，1 'S，5 'S）-2-甲基-6-（4'-亚甲基双环[3.1.0]的雄性聚集信息素的合成和绝对构型]己基）庚-2-烯-1-醇

  摘要：

  确定包括臭虫Erysarcoris lewisi（Distant）雄性产生的聚集信息素的绝对构型的结构为（2 Z，6 R，1 'S，5 'S）-2-甲基-6-（4 '-亚甲基双环[3.1.0]己基）庚-2-烯-1-醇1的生物测定及天然信息素的1 H NMR谱与（2 Z，6 R，1 'S，5'小号） -和（2 ž，6 - [R，1' - [R，5' - [R ）-异构体。这两个非对映异构体是由相应的酮合成的（6R，1 'S，5'R）-和（6 R，1'R，5 'S）-2通过脂肪酶催化（6 R，1 'S，4'的混合物的不对称乙酰化反应）制得小号，5' - [R） -和（6 - [R，1' - [R，4' - [R，5'小号）-7'- norsesquisabinen -4'-醇3。酮2的绝对构型通过与（1 R，5 S）-sabina酮4的CD比较来确定。（2 Z通过使用霍奇森的非对映选择性分子内

  DOI：

  10.1016/j.tetasy.2008.04.029
• 作为产物：
  描述：

  (4R,1'S,5'R)-4-(4'-oxobicyclo[3.1.0]hex-1'-yl)pentanal 、 ethyl 2-(di-o-tolylphosphono)propanoate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到ethyl (2Z,6R,1'S,5'R)-2-methyl-6-(4'-oxobicyclo[3.1.0]hex-1'-yl)hept-2-enoate
  参考文献：
  名称：

  Determination of the absolute configuration of the male aggregation pheromone, 2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol, of the stink bug Erysarcoris lewisi (Distant) as 2Z,6R,1′S,5′S by its synthesis

  摘要：

  Lipase-catalyzed asymmetric acetylation of a mixture of (6R,1'S,4'S,5'R)- and (6R,1'R,4'R,5'S)-7'-norsesquisabinen-4'-ol (3) afforded a separable mixture of the recovered former and the acetate of the latter. The recovered alcohol was oxidized to (6R,1'S,5'R)-sesquisabina ketone (2), whose absolute configuration could be assigned by its CD comparison with (1R,5S)-sabina ketone (4). Conversion of (6R,1'S,5'R)-sesquisabina ketone (2) to the bioactive pheromone revealed the stereostructure of the male aggregation pheromone of the stink bug Erysarcoris lewisi (Distant) to be (2Z,6R,1'S,5'S)-2-methyl-6-(4'-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol (sesquisabinen-1-ol, 1). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.036

文献信息

• Synthesis and absolute configuration of the male aggregation pheromone of the stink bug Erysarcoris lewisi (Distant), (2Z,6R,1′S,5′S)-2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol
  作者：Takuya Tashiro、Kenji Mori

  DOI：10.1016/j.tetasy.2008.04.029

  日期：2008.5

  (6R,1′S,5′R)- and (6R,1′R,5′S)-2, which were prepared by lipase-catalyzed asymmetric acetylation of a mixture of (6R,1′S,4′S,5′R)- and (6R,1′R,4′R,5′S)-7′-norsesquisabinen-4′-ol 3. The absolute configuration of ketone 2 was assigned by its CD comparison with (1R,5S)-sabina ketone 4. An alternative synthesis of (2Z,6R,1′S,5′S)-1 was achieved without recourse to enzyme by employing Hodgson’s diastereoselective

  确定包括臭虫Erysarcoris lewisi（Distant）雄性产生的聚集信息素的绝对构型的结构为（2 Z，6 R，1 'S，5 'S）-2-甲基-6-（4 '-亚甲基双环[3.1.0]己基）庚-2-烯-1-醇1的生物测定及天然信息素的1 H NMR谱与（2 Z，6 R，1 'S，5'小号） -和（2 ž，6 - [R，1' - [R，5' - [R ）-异构体。这两个非对映异构体是由相应的酮合成的（6R，1 'S，5'R）-和（6 R，1'R，5 'S）-2通过脂肪酶催化（6 R，1 'S，4'的混合物的不对称乙酰化反应）制得小号，5' - [R） -和（6 - [R，1' - [R，4' - [R，5'小号）-7'- norsesquisabinen -4'-醇3。酮2的绝对构型通过与（1 R，5 S）-sabina酮4的CD比较来确定。（2 Z通过使用霍奇森的非对映选择性分子内
• Determination of the absolute configuration of the male aggregation pheromone, 2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol, of the stink bug Erysarcoris lewisi (Distant) as 2Z,6R,1′S,5′S by its synthesis
  作者：Kenji Mori、Takuya Tashiro、Tomoko Yoshimura、Masami Takita、Jun Tabata、Shyuntaro Hiradate、Hajime Sugie

  DOI：10.1016/j.tetlet.2007.11.036

  日期：2008.1

  Lipase-catalyzed asymmetric acetylation of a mixture of (6R,1'S,4'S,5'R)- and (6R,1'R,4'R,5'S)-7'-norsesquisabinen-4'-ol (3) afforded a separable mixture of the recovered former and the acetate of the latter. The recovered alcohol was oxidized to (6R,1'S,5'R)-sesquisabina ketone (2), whose absolute configuration could be assigned by its CD comparison with (1R,5S)-sabina ketone (4). Conversion of (6R,1'S,5'R)-sesquisabina ketone (2) to the bioactive pheromone revealed the stereostructure of the male aggregation pheromone of the stink bug Erysarcoris lewisi (Distant) to be (2Z,6R,1'S,5'S)-2-methyl-6-(4'-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol (sesquisabinen-1-ol, 1). (C) 2007 Elsevier Ltd. All rights reserved.