methyl 3-[(1R,3E)-3-ethylidene-1-methyl-2-oxocyclopentyl]propanoate | 918813-53-3

• 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: methyl 3-[(1R,3E)-3-ethylidene-1-methyl-2-oxocyclopentyl]propanoate
• CAS: 918813-53-3
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: FKGZWNDQBWBHBZ-OXFRDRNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  methyl 3-[(1R,3E)-3-ethylidene-1-methyl-2-oxocyclopentyl]propanoate 在 lead(IV) acetate 、 氢氧化钾 、 碘 作用下， 以 甲醇 、 四氯化碳 、 乙醚 为溶剂， 反应 15.5h， 生成 (2R)-2-(2-iodoethyl)-5-isopropyl-2-methylcylopentanone
  参考文献：
  名称：

  Asymmetric synthesis of the tricyclic core of cyathin diterpenoids via intramolecular Heck reaction

  摘要：

  The enantioselective synthesis of the ketones 3 which displays the carbon core of NGF-inducing cyathane diterpenes is described. The key tricyclic trienone 22 was assembled in 13 steps from Michael adduct (R)-8a via intramolecular Heck cyclization of the chiral triflate 21. The trienone 22 was further elaborated into ketone 3 through tritnethylaluminum-promoted expansion of the Gring with trimethylsilyldiazomethane. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.157
• 作为产物：
  描述：

  methyl (1R)-{1-methyl-2-[(trimethylsilyl)oxy]cyclopent-2-en-1-yl}propanoate 在 4-二甲氨基吡啶 、 四氯化钛 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 6.5h， 生成 methyl 3-[(1R,3E)-3-ethylidene-1-methyl-2-oxocyclopentyl]propanoate
  参考文献：
  名称：

  Asymmetric synthesis of the tricyclic core of cyathin diterpenoids via intramolecular Heck reaction

  摘要：

  The enantioselective synthesis of the ketones 3 which displays the carbon core of NGF-inducing cyathane diterpenes is described. The key tricyclic trienone 22 was assembled in 13 steps from Michael adduct (R)-8a via intramolecular Heck cyclization of the chiral triflate 21. The trienone 22 was further elaborated into ketone 3 through tritnethylaluminum-promoted expansion of the Gring with trimethylsilyldiazomethane. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.157

文献信息

• Asymmetric synthesis of the tricyclic core of cyathin diterpenoids via intramolecular Heck reaction
  作者：Emmanuelle Drège、Georges Morgant、Didier Desmaële

  DOI：10.1016/j.tetlet.2005.07.157

  日期：2005.10

  The enantioselective synthesis of the ketones 3 which displays the carbon core of NGF-inducing cyathane diterpenes is described. The key tricyclic trienone 22 was assembled in 13 steps from Michael adduct (R)-8a via intramolecular Heck cyclization of the chiral triflate 21. The trienone 22 was further elaborated into ketone 3 through tritnethylaluminum-promoted expansion of the Gring with trimethylsilyldiazomethane. (c) 2005 Elsevier Ltd. All rights reserved.