(2S,3S,4S)-tert-butyl 2,3-bis(4-chlorobenzoyl)-4-(2-oxoethyl)-3,4-dihydro-1H-carbazole-9(2H)-carboxylate | 1360110-57-1

• 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-bis(4-chlorobenzoyl)-4-(2-oxoethyl)-3,4-dihydro-1H-carbazole-9(2H)-carboxylate
• CAS: 1360110-57-1
• 化学式: C₃₃H₂₉Cl₂NO₅
• 分子量: 590.503
• InChiKey: LVHYPZARYWEHOX-AHPZMPFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.96
• 重原子数：
  41.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.44
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-tert-butyl 2,3-bis(4-chlorobenzoyl)-4-(2-oxoethyl)-3,4-dihydro-1H-carbazole-9(2H)-carboxylate 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 sodium acetate 作用下， 以 甲苯 为溶剂， 反应 40.0h， 生成 、 (3S,3aS,4S,10cS)-tert-butyl 4-(4-chlorobenzoyl)-3-(4-chlorophenyl)-3-hydroxy-2-oxo-1,3,3a,4,5,10c-hexahydrocyclopenta[c]carbazole-6(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
• 作为产物：
  描述：

  (E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione 、 tert-butyl 2-methyl-3-(3-oxoprop-1-enyl)-1H-indole-1-carboxylate 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， 以76%的产率得到(2S,3S,4S)-tert-butyl 2,3-bis(4-chlorobenzoyl)-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