methyl (3aR,5aR,8aS,8bS)-2,3,3a,5a,7,8,8a,8b-octahydrofuro[2,3-g]indole-1-carboxylate | 130760-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (3aR,5aR,8aS,8bS)-2,3,3a,5a,7,8,8a,8b-octahydrofuro[2,3-g]indole-1-carboxylate
• CAS: 130760-75-7
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: RONOCBYQMDLQSA-ZDCRXTMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (3aS,6S,7R,7aR)-6-Hydroxy-7-(2-hydroxy-ethyl)-2,3,3a,6,7,7a-hexahydro-indole-1-carboxylic acid methyl ester 在 1,1-二甲氧基-N,N-二甲基乙胺 作用下， 以 xylene 为溶剂， 以75%的产率得到methyl (3aR,5aR,8aS,8bS)-2,3,3a,5a,7,8,8a,8b-octahydrofuro[2,3-g]indole-1-carboxylate
  参考文献：
  名称：

  Total synthesis of (dl)-stenine

  摘要：

  Intramolecular Diels-Alder cycloadduct 10 was converted to the Stemona alkaloid stenine (1) via a reaction sequence that features a Curtius rearrangement (12 --> 13), Eschenmoser-Claisen rearrangement (19 --> 20) and stereoselective free radical allylation (4 --> 21).

  DOI：

  10.1021/jo00313a003

文献信息

• A Diels-Alder approach to Stemona alkaloids: total synthesis of stenine
  作者：Cheng Yi Chen、David J. Hart

  DOI：10.1021/jo00067a015

  日期：1993.7

  A total synthesis of dl-stenine (4) is described. Key features involve (1) use of an intramolecular Diels-Alder cycloaddition-aminimide rearrangement sequence to construct the perhydroindole substructure (29 --> 36 --> 27), (2) application of an Eschenmoser-Claisen rearrangement-iodolactonization sequence to prepare the butenolide substructure (58 --> 59 --> 61), (3) use of a free-radical allylation to introduce the C(9)-ethyl group (61 --> 62), and (4) thermal cyclization of an amino ester to afford azepinone 68. A variety of intermolecular and intramolecular Diels-Alder reactions, including examples in which alpha,beta-unsaturated thioesters play the role of dienophile, are also described.
• CHEN, CHENG-YI;HART, DAVID J., J. ORG. CHEM., 55,(1990) N6, C. 6236-6240
  作者：CHEN, CHENG-YI、HART, DAVID J.

  DOI：——

  日期：——