(R)-methyl 4a-methyl-4a,9-dihydro-4H-carbazole-1-carboxylate | 1449683-75-3

• 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: (R)-methyl 4a-methyl-4a,9-dihydro-4H-carbazole-1-carboxylate
• 英文别名: methyl (4aR)-4a-methyl-4,9-dihydrocarbazole-1-carboxylate
• CAS: 1449683-75-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: BDVTVJORNDYHAF-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl 4a-methyl-4a,9-dihydro-4H-carbazole-1-carboxylate 、 N-(4-溴苯基)马来酰亚胺 以 甲苯 为溶剂， 反应 1.5h， 以95%的产率得到C₂₅H₂₁BrN₂O₄
  参考文献：
  名称：

  Enantioselective Intermolecular Formal [3 + 3] Cycloaddition of 2,3-Disubstituted Indoles with Acrolein

  摘要：

  An expedient enantioselective synthesis of highly substituted hydrocarbazoles has been realized by an organocatalyzed formal [3 + 3] cycloaddition between acrolein and 2,3-disubstituted indoles. Tricyclic hydrocarbazoles were obtained from a broad range of 2,3-disubstituted indoles and acrolein in good to excellent yields and excellent enantioselectivites.

  DOI：

  10.1021/ol401809d
• 作为产物：
  描述：

  (3-methyl-1H-indol-2-yl)acetic acid methyl ester 、 丙烯醛 在 邻硝基苯甲酸 、 quinidine 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到(R)-methyl 4a-methyl-4a,9-dihydro-4H-carbazole-1-carboxylate
  参考文献：
  名称：

  Enantioselective Intermolecular Formal [3 + 3] Cycloaddition of 2,3-Disubstituted Indoles with Acrolein

  摘要：

  An expedient enantioselective synthesis of highly substituted hydrocarbazoles has been realized by an organocatalyzed formal [3 + 3] cycloaddition between acrolein and 2,3-disubstituted indoles. Tricyclic hydrocarbazoles were obtained from a broad range of 2,3-disubstituted indoles and acrolein in good to excellent yields and excellent enantioselectivites.

  DOI：

  10.1021/ol401809d

文献信息

• Enantioselective Intermolecular Formal [3 + 3] Cycloaddition of 2,3-Disubstituted Indoles with Acrolein
  作者：Jianbiao Huang、Long Zhao、Yong Liu、Weiguo Cao、Xiaoyu Wu

  DOI：10.1021/ol401809d

  日期：2013.9.6

  An expedient enantioselective synthesis of highly substituted hydrocarbazoles has been realized by an organocatalyzed formal [3 + 3] cycloaddition between acrolein and 2,3-disubstituted indoles. Tricyclic hydrocarbazoles were obtained from a broad range of 2,3-disubstituted indoles and acrolein in good to excellent yields and excellent enantioselectivites.