1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate | 161201-95-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate
• CAS: 161201-95-2
• 化学式: C₃₂H₃₉IN₂O₆S
• 分子量: 706.642
• InChiKey: JPRNKCCBYNWKOS-BBFBZJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103.7
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate 在 palladium diacetate 、 thallium(I) acetate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 60.0h， 以69%的产率得到(7R,9R,9aS)-2-Benzenesulfonyl-7-methyl-6-oxo-2,6,7,8,9,9a-hexahydro-2,6a-diaza-cyclopenta[d]acenaphthylene-7,9-dicarboxylic acid 9-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester 7-methyl ester
  参考文献：
  名称：

  Sequential and cascade 1,3-dipolar cycloaddition-palladium catalysed carbonylation-cyclisation reactions. Diastereospecific and homochiral processes

  摘要：

  Combinations of imine --> azomethine ylide --> cycloaddition cascades with Pd(0) catalysed cyclisation-carbonylation forming 5- and 6-membered lactams in sequential reactions are described and both diastereospecific and homochiral examples are provided, The azomethine ylides can be generated either via thermal 1,2-prototropy or metal ion catalysis at ambient temperature. The former sequence has been combined with the Pd(0) catalysed cascade into a one-pot protocol.

  DOI：

  10.1016/0040-4020(94)00956-u
• 作为产物：
  描述：

  1-(Benzenesulfonyl)-4-iodoindole-3-carbaldehyde 在 silver(I) acetate 、 magnesium sulfate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.5h， 生成 1S,2R,5S-menthyl r-2S-methoxycarbonyl-2-methyl-c-5S-(4'-iodo-N-phenylsuphonylindol-3'-yl)pyrrolidine-c-4R-carboxylate
  参考文献：
  名称：

  Sequential and cascade 1,3-dipolar cycloaddition-palladium catalysed carbonylation-cyclisation reactions. Diastereospecific and homochiral processes

  摘要：

  Combinations of imine --> azomethine ylide --> cycloaddition cascades with Pd(0) catalysed cyclisation-carbonylation forming 5- and 6-membered lactams in sequential reactions are described and both diastereospecific and homochiral examples are provided, The azomethine ylides can be generated either via thermal 1,2-prototropy or metal ion catalysis at ambient temperature. The former sequence has been combined with the Pd(0) catalysed cascade into a one-pot protocol.

  DOI：

  10.1016/0040-4020(94)00956-u