(R)-2-ethyl-2-(2-methoxycarbonylethyl) cyclopentanone | 134983-93-0

• 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: (R)-2-ethyl-2-(2-methoxycarbonylethyl) cyclopentanone
• CAS: 134983-93-0
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: JBWHFLOARWMIAT-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-ethyl-2-(2-methoxycarbonylethyl) cyclopentanone 在 四氧化钌 sodium periodate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 苯 为溶剂， 反应 48.0h， 生成 ((R)-1-Ethyl-2-oxo-cyclopentyl)-acetic acid methyl ester
  参考文献：
  名称：

  Asymmetric Michael addition of chiral imines to phenylvinylsulfone: Preparation of key chiral building blocks for the synthesis of Aspidosperma and Hunteria alkaloids.

  摘要：

  Addition of chiral imine 8 to phenylvinylsulfone 9 led, after hydrolytic work-up to adduct 11 (91 % stereoselectivity). This derivative has been converted into target cyclopentanones 14 and 16.

  DOI：

  10.1016/s0957-4166(00)82358-7
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 24.0h， 生成 (R)-2-ethyl-2-(2-methoxycarbonylethyl) cyclopentanone
  参考文献：
  名称：

  Asymmetric Michael addition of chiral imines to phenylvinylsulfone: Preparation of key chiral building blocks for the synthesis of Aspidosperma and Hunteria alkaloids.

  摘要：

  Addition of chiral imine 8 to phenylvinylsulfone 9 led, after hydrolytic work-up to adduct 11 (91 % stereoselectivity). This derivative has been converted into target cyclopentanones 14 and 16.

  DOI：

  10.1016/s0957-4166(00)82358-7

文献信息

• Stereocontrolled elaboration of quaternary carbon centers involving the asymmetric michael-type alkylation of chiral imines: an efficient enantioselective access to (+)-vincamine
  作者：Jose C.F. Alves、Alessandro B.C. Simas、Paulo R.R. Costa、Jean d'Angelo

  DOI：10.1016/s0957-4166(97)00210-3

  日期：1997.6

  Michael adduct , resulting from the condensation of chiral imine 4 with methyl acrylate, was transformed in two steps into lactone . Tryptamine-induced ring-opening of this lactone gave 9, which was finally converted in three steps into the key tricyclic derivative , a known precursor of (+)-vincamine 1.

  手性亚胺4与丙烯酸甲酯缩合而得的迈克尔加合物分两步转化为内酯。由色胺酮引起的内酯开环生成9，最终将其分三步转化为关键的三环衍生物，即已知的（+）-长春胺1的前体。
• Formal enantioselective synthesis of (+)-vincamine. The first enantioselective route to (+)-3,14-epivincamine and its enantiomer
  作者：José C.F Alves、Alessandro B.C Simas、Paulo R.R Costa

  DOI：10.1016/s0957-4166(98)00489-3

  日期：1999.1

  A formal synthesis of (+)- vincamine (1) from (S)-(+)- 2-ethyl-2-(2-methoxycarbonylethyl) cyclopentanone (6a) is described. This intermediate had previously been obtained by our research group in 90% ee through d'Angelo's deracemizing alkylation of the chiral imine 7, easily prepared from (R)-(+)-alpha-methylbenzylamine and 2-ethyl cyclopentanone with methyl acrylate. A potencial advanced intermediate for the synthesis of (+)-4, an epimer of (+)-1 at positions C-3 and C-14, has also been prepared from 6a. (C) 1999 Elsevier Science Ltd. All rights reserved.