(2S,3S,4S)-tert-butyl 2,3-dibenzoyl-4-(2-oxoethyl)-3,4-dihydro-1H-carbazole-9(2H)-carboxylate | 1360110-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2S,3S,4S)-tert-butyl 2,3-dibenzoyl-4-(2-oxoethyl)-3,4-dihydro-1H-carbazole-9(2H)-carboxylate
• 英文别名: tert-butyl (2S,3S,4S)-2,3-dibenzoyl-4-(2-oxoethyl)-1,2,3,4-tetrahydrocarbazole-9-carboxylate
• CAS: 1360110-55-9
• 化学式: C₃₃H₃₁NO₅
• 分子量: 521.613
• InChiKey: QJWLONWQUDNEON-AHPZMPFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 2-methyl-3-(3-oxoprop-1-enyl)-1H-indole-1-carboxylate 、 反-1,2-二苯酰乙烯 在 (2R)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 2,4,6-三甲基苯甲酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 、 (2S,3S,4S)-tert-butyl 2,3-dibenzoyl-4-(2-oxoethyl)-3,4-dihydro-1H-carbazole-9(2H)-carboxylate
  参考文献：
  名称：

  Multicatalytic Asymmetric Synthesis of Complex Tetrahydrocarbazoles via a Diels–Alder/Benzoin Reaction Sequence

  摘要：

  Expanding upon the recently developed aminocatalytic asymmetric indole-2,3-quinodimethane strategy, a straightforward synthesis of structurally and stereochemically complex tetrahydrocarbazoles has been devised. The chemistry's complexity-generating power was further harnessed by designing a multicatalytic, one-pot Diels-Alder/benzoin reaction sequence to stereoselectively access trans-fused tetracyclic indole-based compounds having four stereogenic centers with very high fidelity.

  DOI：

  10.1021/ol300192p

文献信息

• Multicatalytic Asymmetric Synthesis of Complex Tetrahydrocarbazoles via a Diels–Alder/Benzoin Reaction Sequence
  作者：Yankai Liu、Manuel Nappi、Eduardo C. Escudero-Adán、Paolo Melchiorre

  DOI：10.1021/ol300192p

  日期：2012.3.2

  Expanding upon the recently developed aminocatalytic asymmetric indole-2,3-quinodimethane strategy, a straightforward synthesis of structurally and stereochemically complex tetrahydrocarbazoles has been devised. The chemistry's complexity-generating power was further harnessed by designing a multicatalytic, one-pot Diels-Alder/benzoin reaction sequence to stereoselectively access trans-fused tetracyclic indole-based compounds having four stereogenic centers with very high fidelity.