dimethyl 1-(methylsulfonyl)-2-phenyl-2,3,5,6,7,7a-hexahydro-1H-6,7-indoledicarboxylate

• 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: dimethyl 1-(methylsulfonyl)-2-phenyl-2,3,5,6,7,7a-hexahydro-1H-6,7-indoledicarboxylate
• 英文别名: dimethyl (2R,6S,7S,7aS)-1-methylsulfonyl-2-phenyl-2,3,5,6,7,7a-hexahydroindole-6,7-dicarboxylate
• 化学式: C₁₉H₂₃NO₆S
• 分子量: 393.461
• InChiKey: VTEFASLBGKTGDJ-VVLHAWIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  马来酸二甲酯 、 1-mesyl-3-vinyl-5-phenyl-4,5-dihydropyrrole 以 甲苯 为溶剂， 反应 20.0h， 以80%的产率得到dimethyl 1-(methylsulfonyl)-2-phenyl-2,3,5,6,7,7a-hexahydro-1H-6,7-indoledicarboxylate
  参考文献：
  名称：

  Synthesis, Reactivity and Demetallation of Tungsten–Azacyclic Carbeniums via Cycloalkenation of Tungsten–Alkynylamine Compounds

  摘要：

  Treatment of tungsten-eta(1)-alpha,delta-alkynylamine compounds with aldehyde and BF3. Et2O led to cycloalkenation reaction, giving good yields of tungsten-eta(1)-pyrrolylidium salts. These azacyclic carbeniums provide a short synthesis of alpha-alkylidene-gamma-lactam via oxidation with m-CPBA. In contrast with tungsten-eta(1)-oxacyclic carbenium, this salt reacts with one molecule of organometallic reagents such as NaBH3CN, CH3MgBr and Me2CuLi to give tungsten-eta(1)-4,5-dihydropyrrole complexes. An alternative use of this cyclialkenation is to provide a short synthesis of 3-vinyl-Delta(2)-pyrrolines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00215-5

文献信息

• Synthesis, Reactivity and Demetallation of Tungsten–Azacyclic Carbeniums via Cycloalkenation of Tungsten–Alkynylamine Compounds
  作者：Ming-Jung Chen、Shie-Tsung Chang、Rai-Shung Liu

  DOI：10.1016/s0040-4020(00)00215-5

  日期：2000.7

  Treatment of tungsten-eta(1)-alpha,delta-alkynylamine compounds with aldehyde and BF3. Et2O led to cycloalkenation reaction, giving good yields of tungsten-eta(1)-pyrrolylidium salts. These azacyclic carbeniums provide a short synthesis of alpha-alkylidene-gamma-lactam via oxidation with m-CPBA. In contrast with tungsten-eta(1)-oxacyclic carbenium, this salt reacts with one molecule of organometallic reagents such as NaBH3CN, CH3MgBr and Me2CuLi to give tungsten-eta(1)-4,5-dihydropyrrole complexes. An alternative use of this cyclialkenation is to provide a short synthesis of 3-vinyl-Delta(2)-pyrrolines. (C) 2000 Elsevier Science Ltd. All rights reserved.