propan-2-yl 3-[(3S)-3-ethyl-2-oxooxan-3-yl]propanoate | 192824-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: propan-2-yl 3-[(3S)-3-ethyl-2-oxooxan-3-yl]propanoate
• CAS: 192824-47-8
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: SEMRTVPELFJJRN-ZDUSSCGKSA-N

物化性质

• 沸点：
  345.0±15.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  propan-2-yl 3-[(3S)-3-ethyl-2-oxooxan-3-yl]propanoate 在 18-冠醚-6 、 四溴化碳 、 potassium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 (S)-3-ethyl-1-<2-(1H-indol-3-yl)ethyl>-2-oxo-3-piperidine propanoic acid isopropyl ester
  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
• 作为产物：
  描述：

  2-乙基环戊酮 在 盐酸 、 sodium tetrahydroborate 、 氧气 、 sodium isopropylate 、 对甲苯磺酸 、 臭氧 、 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 61.17h， 生成 propan-2-yl 3-[(3S)-3-ethyl-2-oxooxan-3-yl]propanoate
  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 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.