(S)-(+)-2-ethyl-2-2'-carboxymethyl-ethylcyclopentanone | 152266-60-9

• 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: (S)-(+)-2-ethyl-2-2'-carboxymethyl-ethylcyclopentanone
• 英文别名: (S)-2-ethyl-2-(2-methoxycarbonylethyl) cyclopentanone；methyl 3-[(1S)-1-ethyl-2-oxocyclopentyl]propanoate
• CAS: 152266-60-9
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: JBWHFLOARWMIAT-NSHDSACASA-N

物化性质

• 沸点：
  268.3±13.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (S)-(+)-2-ethyl-2-2'-carboxymethyl-ethylcyclopentanone 在 sodium tetrahydroborate 、 sodium isopropylate 、 臭氧 、 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 0.75h， 生成 (2S)-2-ethyl-2-(3-hydroxypropyl)-5-oxo-5-propan-2-yloxypentanoic acid
  参考文献：
  名称：

  涉及手性亚胺的不对称迈克尔型烷基化的季碳中心的立体控制修饰：对（+）-长春胺的有效对映选择性

  摘要：

  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。

  DOI：

  10.1016/s0957-4166(97)00210-3
• 作为产物：
  描述：

  2-乙基环戊酮 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 54.0h， 生成 (S)-(+)-2-ethyl-2-2'-carboxymethyl-ethylcyclopentanone
  参考文献：
  名称：

  Formal enantioselective synthesis of (+)-vincamine. The first enantioselective route to (+)-3,14-epivincamine and its enantiomer

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(98)00489-3

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 synthesis of (−)-Vallesamidine A 2,2,3-trialkylindoline alkaloid
  作者：Paulo R.R. Costa、Rosane N. Castro、Florence M.C. Farias、Octavio A.C. Antunes、Lothar Bergter

  DOI：10.1016/s0957-4166(00)80350-x

  日期：1993.7

  (S)-(+)-2-ethyl-2[2'-carboxymethyl]cyclopentanone 6 was prepared regio- and enantioselectively (ee = 90%) by ''deracemizing alkylation'' of the chiral imine 5 with methylacrylate. Compound 6 was transformed into the bicyclic imine (R)-(+)-3. This intermediate was used by Heathcock, in the racemic form, to the total synthesis of (+/-)-Vallesamidine 1, a 2,2,3-trialkylindoline alkaloid.
• Asymmetric Michael addition of chiral imines to phenylvinylsulfone: Preparation of key chiral building blocks for the synthesis of Aspidosperma and Hunteria alkaloids.
  作者：Jean d'Angelo、Gilbert Revial、Paulo R.R. Costa、Rosane N. Castro、Octavio A.C. Antunes

  DOI：10.1016/s0957-4166(00)82358-7

  日期：1991.1

  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.
• 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.