(3aS,10aS,10bS)-2-methyl-10-(2,2,2-trifluoroacetyl)-3a,4,10,10a-tetrahydropyrrolo[3,4-a]carbazole-1,3(2H,10bH)-dione | 1104643-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3aS,10aS,10bS)-2-methyl-10-(2,2,2-trifluoroacetyl)-3a,4,10,10a-tetrahydropyrrolo[3,4-a]carbazole-1,3(2H,10bH)-dione
• 英文别名: (3aS,10aS,10bS)-2-methyl-10-(2,2,2-trifluoroacetyl)-3a,4,10a,10b-tetrahydropyrrolo[3,4-a]carbazole-1,3-dione
• CAS: 1104643-73-3
• 化学式: C₁₇H₁₃F₃N₂O₃
• 分子量: 350.297
• InChiKey: QTBBULOJZQCCOB-WCFLWFBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-vinylindole 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3aS,10aS,10bS)-2-methyl-10-(2,2,2-trifluoroacetyl)-3a,4,10,10a-tetrahydropyrrolo[3,4-a]carbazole-1,3(2H,10bH)-dione
  参考文献：
  名称：

  Enantioselective synthesis of functionalised tetrahydrocarbazoles via an organocatalysed Diels–Alder/ene reaction strategy

  摘要：

  Functionalised tetrahydrocarbazoles are accessed through an enantioselective organocatalysed Diels-Alder reaction of 3-vinyl-1H-indole with a suitable dienophile in combination with an in situ N-protection. A subsequent diastereospecific ene reaction is then used to transfer chirality from the 10a to the 5 position with rearomatisation of the indolic ring, to give the target tetrahydrocarbazoles with high % ee. The in situ introduction of different N-protecting groups is explored along with their influence on the subsequent ene reactions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.09.004

文献信息

• Asymmetric Diels-Alder Reactions of Vinylindoles Using Organocatalysis
  作者：Luca Bernardi、Alfredo Ricci、Claudio Gioia

  DOI：10.1055/s-0029-1217046

  日期：2010.1

  The different behavior of 3- and 2-vinylindoles in Diels-Alder cycloaddition reactions in the presence of bifunctional hydrogen bond donor organocatalysts is described. asymmetric catalysis - Diels-Alder reactions - kinetic resolution - organocatalysis - vinylindoles

  描述了在双官能氢键供体有机催化剂存在下，Diels-Alder环加成反应中3-和2-乙烯基吲哚的不同行为。 不对称催化-Diels-Alder反应-动力学拆分-有机催化-乙烯基吲哚
• Organocatalytic Asymmetric Diels–Alder Reactions of 3‐Vinylindoles
  作者：Claudio Gioia、Agnès Hauville、Luca Bernardi、Francesco Fini、Alfredo Ricci

  DOI：10.1002/anie.200804275

  日期：2008.11.17