cis-9-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-9H-carbazole

• 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: cis-9-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-9H-carbazole
• 英文别名: cis-4-(Carbazol-9-yl)-2-methyl-1,2,3,4-tetrahydroquinoline；9-[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]carbazole
• 化学式: C₂₂H₂₀N₂
• 分子量: 312.414
• InChiKey: PBFZEJQXRCOERQ-OYHNWAKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  16.96
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-乙烯基咔唑 、 苯胺 在 三氯化锑 作用下， 以 乙腈 为溶剂， 反应 1.58h， 以51%的产率得到cis-9-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-9H-carbazole
  参考文献：
  名称：

  一锅药用重要的顺式-2-甲基-4-氨基取代的1,2,3,4-四氢喹啉

  摘要：

  简单合成具有医学重要性的顺式-2-甲基-4-氮杂泛-2-1-2-，1,2,3,4-四氢喹啉/顺式-9-（2-甲基1,2,3,4-四氢喹啉-4 -yl）-9 H-咔唑的报道。以三氯化锑为催化剂，乙腈为溶剂，通过亚氨基Diels-Alder反应，与苯胺和N-乙烯基己内酰胺/ N-乙烯基咔唑进行多组分一锅合成。NMR技术（2D）用于研究新合成化合物的区域和立体化学。产品的顺式非对映选择性是通过COZY和NOESY研究预测的。

  DOI：

  10.1002/cjoc.201100180

文献信息

• Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00118a014

  日期：1995.6

  Reactions of N-alkyl-N-phenyl-1H-benzotriazole-1-methanamines 1 with N-vinyl-2-pyrrolidinone and with N-vinyl-N-methylacetamide give 4-(2-pyrrolidinon-1-yl)- and 4-(N-methylacetamido-N-yl)-1,2,3 ,4-tetrahydroquinolines (5 and 32), respectively. In a reaction with N-vinyl-2-pyrrolidinone, alpha-alkyl (11) and alpha-aryl(18) derivatives of 1 stereoselectively give cis-2,4-disubstituted tetrahydroquinolines 16 and 21, respectively. The 2-pyrrolidinon-1-yl and acetamido-N-yl substituents in the products are reduced with lithium aluminum hydride to the corresponding amino groups. Similar reactions of N-phenyl-1H-benzotriazole-1-methanamines 1 with 9-vinylcarbazole (40) lead to the corresponding 4-(carbazol-9-yl)-1,2,3,4-tetrahydroquinolines (41 and 42) and/or analogous 4-(benzotriazol-1-yl) or 4-(benzotriazol-2-yl) derivatives (37, 38, 43, and 44), depending on the nature of the starting material and the reaction conditions. By commencing with aniline derivatives in which the nitrogen atom is built into a heterocyclic system, this method allows for the addition of a another ring to the system, as exemplified by the conversion of phenothiazine into 46 and [3,1]benzoxazine into 49, 52, and 53.
• One Pot Synthesis of Medicinally Important cis-2-Methyl-4-amino substituted-1,2,3,4-tetrahydroquinolines
  作者：Kumar H. C. Kiran、K. M. Mahadevan、Varma P. Prabhakara、A. Srinivasa

  DOI：10.1002/cjoc.201100180

  日期：2012.3

  A simple synthesis of medicinally important cis‐2‐methyl‐4‐azapan‐2‐one‐1,2,3,4‐tetrahydroquinolines/cis‐9‐(2‐methyl‐1,2,3,4‐tetrahydroquinolin‐4‐yl)‐9H‐carbazole was reported. Multicomponent one pot synthesis with anilines and N‐vinylcaprolactam/N‐vinyl carbazole via imino Diels‐Alder reaction by using antimony trichloride as catalyst and acetonitrile as solvent was employed. NMR technique (2D) was

  简单合成具有医学重要性的顺式-2-甲基-4-氮杂泛-2-1-2-，1,2,3,4-四氢喹啉/顺式-9-（2-甲基1,2,3,4-四氢喹啉-4 -yl）-9 H-咔唑的报道。以三氯化锑为催化剂，乙腈为溶剂，通过亚氨基Diels-Alder反应，与苯胺和N-乙烯基己内酰胺/ N-乙烯基咔唑进行多组分一锅合成。NMR技术（2D）用于研究新合成化合物的区域和立体化学。产品的顺式非对映选择性是通过COZY和NOESY研究预测的。