(1R,2R)-ethyl 2-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxocyclopentanecarboxylate | 1260612-71-2

• 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: (1R,2R)-ethyl 2-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxocyclopentanecarboxylate
• 英文别名: ethyl (1R,2R)-2-methyl-1-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-5-oxocyclopentane-1-carboxylate
• CAS: 1260612-71-2
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: DVLWYTOVAUIOGE-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R)-ethyl 2-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxocyclopentanecarboxylate 在 palladium diacetate 、 sodium hexamethyldisilazane 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 45.0 ℃ 、101.33 kPa 条件下， 反应 32.5h， 生成 (1R,5R)-1-ethyl 2-methyl 5-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclopent-2-ene-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of the Cyclohexane Core of Phomactins and a New Route to the Bicyclo[9.3.1]pentadecane Diterpenoid Skeleton

  摘要：

  Conjugate reduction of an enone accompanied by in situ intramolecular aldol condensation was used to construct the tetrasubstituted cyclohexane nucleus of phomactins. Subsequent relay ring-closing metathesis completed the nine-membered ansa bridge of the diterpenoid framework.

  DOI：

  10.1021/ol1026816
• 作为产物：
  描述：

  (2R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate 在 三氟甲磺酸三甲基硅酯 、 caesium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 30.17h， 生成 (1R,2R)-ethyl 2-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Synthesis of the Cyclohexane Core of Phomactins and a New Route to the Bicyclo[9.3.1]pentadecane Diterpenoid Skeleton

  摘要：

  Conjugate reduction of an enone accompanied by in situ intramolecular aldol condensation was used to construct the tetrasubstituted cyclohexane nucleus of phomactins. Subsequent relay ring-closing metathesis completed the nine-membered ansa bridge of the diterpenoid framework.

  DOI：

  10.1021/ol1026816

文献信息

• Synthesis of the Cyclohexane Core of Phomactins and a New Route to the Bicyclo[9.3.1]pentadecane Diterpenoid Skeleton
  作者：Keith D. Schwartz、James D. White

  DOI：10.1021/ol1026816

  日期：2011.1.21

  Conjugate reduction of an enone accompanied by in situ intramolecular aldol condensation was used to construct the tetrasubstituted cyclohexane nucleus of phomactins. Subsequent relay ring-closing metathesis completed the nine-membered ansa bridge of the diterpenoid framework.