(1S,2R,5R)-methyl 2-methyl-5-(prop-1-en-2-yl)cyclopentanecarboxylate | 177565-49-0

• 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: (1S,2R,5R)-methyl 2-methyl-5-(prop-1-en-2-yl)cyclopentanecarboxylate
• 英文别名: methyl (1S,2R,5R)-2-methyl-5-prop-1-en-2-ylcyclopentane-1-carboxylate
• CAS: 177565-49-0
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: RCJDOVCGMGATJJ-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R)-methyl 2-methyl-5-(prop-1-en-2-yl)cyclopentanecarboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 [(1S,2R,5R)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methanol
  参考文献：
  名称：

  通过双环羰基内酯与丙酸烯丙酯的环加成反应合成Guaianolide环系

  摘要：

  通过Rh 2（OAc）4催化的反应从重氮酮前体生成带有反式环戊烷环的环状羰基内酯，并用丙酸烯丙酯捕获。1,3-偶极环加成导致氧桥联多环的立体选择性形成。通过库尔蒂乌斯降解，将环加合物转变为倍半萜内酯的倍半萜内酯家族的典型环骨架。

  DOI：

  10.1021/ol1012185
• 作为产物：
  描述：

  methyl (1R,2S,3R,5R)-2-methyl-3-(((methylthio)carbonothioyl)oxy)-5-(prop-1-en-2-yl)cyclopentane-1-carboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以6.9 g的产率得到(1S,2R,5R)-methyl 2-methyl-5-(prop-1-en-2-yl)cyclopentanecarboxylate
  参考文献：
  名称：

  通过双环羰基内酯与丙酸烯丙酯的环加成反应合成Guaianolide环系

  摘要：

  通过Rh 2（OAc）4催化的反应从重氮酮前体生成带有反式环戊烷环的环状羰基内酯，并用丙酸烯丙酯捕获。1,3-偶极环加成导致氧桥联多环的立体选择性形成。通过库尔蒂乌斯降解，将环加合物转变为倍半萜内酯的倍半萜内酯家族的典型环骨架。

  DOI：

  10.1021/ol1012185

文献信息

• The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways
  作者：Glenn W. Dawson、John A. Pickett、Diane W.M. Smiley

  DOI：10.1016/0968-0896(96)00012-0

  日期：1996.3

  Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactune, (1R,4aS,7S,7aR)-nepetalactol and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols required samples authenticated by H-1 and C-13 NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclisation of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of molecular biology required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labelling, particularly 8-oxidised monoterpene alcohols and aldehydes. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of the Guaianolide Ring System via Cycloaddition of a Bicyclic Carbonyl Ylide with Allyl Propiolate
  作者：Vaidotas Navickas、Dmitry B. Ushakov、Martin E. Maier、Markus Ströbele、H.-Jürgen Meyer

  DOI：10.1021/ol1012185

  日期：2010.8.6

  trans-annulated cyclopentane ring was generated by a Rh2(OAc)4-catalyzed reaction from a diazoketone precursor and trapped with allyl propiolate. The 1,3-dipolar cycloaddition led to the stereoselective formation of an oxygen-bridged polycycle. Via Curtius degradation, the cycloadduct was transformed to the ring skeleton typical of the sesquiterpene family of guaianolides.

  通过Rh 2（OAc）4催化的反应从重氮酮前体生成带有反式环戊烷环的环状羰基内酯，并用丙酸烯丙酯捕获。1,3-偶极环加成导致氧桥联多环的立体选择性形成。通过库尔蒂乌斯降解，将环加合物转变为倍半萜内酯的倍半萜内酯家族的典型环骨架。