3-((S)-1-Ethyl-2-trimethylsilanyloxy-cyclopent-2-enyl)-propionic acid isopropyl ester | 192824-46-7

• 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: 3-((S)-1-Ethyl-2-trimethylsilanyloxy-cyclopent-2-enyl)-propionic acid isopropyl ester
• CAS: 192824-46-7
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: LVSGBJINKDFTOT-INIZCTEOSA-N

物化性质

• 沸点：
  317.1±25.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-((S)-1-Ethyl-2-trimethylsilanyloxy-cyclopent-2-enyl)-propionic acid isopropyl ester 在 盐酸 、 sodium tetrahydroborate 、 18-冠醚-6 、 四溴化碳 、 sodium perchlorate 、 水 、 氧气 、 potassium hydride 、 臭氧 、 三苯基膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 59.92h， 生成 (15S)-15-ethyl-11-aza-1-azoniapentacyclo[9.7.2.02,7.08,19.015,20]icosa-1,3,5,7,19-pentaen-18-one;perchlorate
  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：

  在 sodium isopropylate 、 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 异丙醇 为溶剂， 反应 49.92h， 生成 3-((S)-1-Ethyl-2-trimethylsilanyloxy-cyclopent-2-enyl)-propionic 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

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。