2,3-二氢-1,3-二甲基喹啉-4(1H)-酮 | 53207-49-1

• 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
• 中文名称: 2,3-二氢-1,3-二甲基喹啉-4(1H)-酮
• 英文名称: 1,3-Dimethyl-2,3-dihydro-4-quinolinone
• 英文别名: 1,3-dimethyl-2,3-dihydro-1H-quinolin-4-one；1,3-Dimethyl-2,3-dihydroquinolin-4(1h)-one；1,3-dimethyl-2,3-dihydroquinolin-4-one
• CAS: 53207-49-1
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: IWTPNBHUUFMRKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为产物：
  描述：

  1,3-Dimethyl-4-(phenylamino)-1,2-dihydroquinoline 在 盐酸 作用下， 反应 0.17h， 生成 2,3-二氢-1,3-二甲基喹啉-4(1H)-酮
  参考文献：
  名称：

  A Versatile Method for the Preparation of Substituted 1,2,3,4-Tetrahydroquinolines

  摘要：

  N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 1 react with acetaldehyde to give 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 11 in good yields along with minor amounts of diamines 12. Reactions of 1 with higher enolizable aldehydes R(1)CH(2)CHO lead to 4-(benzotriazol-1-yl)tetrahydroquinolines with an R(1) substituent at C-3 (17, 18). Condensation of N-methylaniline with two molecules of aldehyde RCH(2)CHO and one molecule of benzotriazole produces 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 34 bearing an R substituent at C-3 and RCH(2) on C-2. In all of these products, the benzotriazol-1-yl moiety can be replaced by a hydrogen atom (by reduction with lithium aluminum hydride) or by an alkyl or aryl group (by reaction with a Grignard reagent). Treatment of 11 with sodium alkoxides leads to 4-alkoxy-1,2,3,4-tetrahydroquinolines 10. Elimination of a molecule of nitrogen from the benzotriazole system of 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 17, 18, and 35 by sodium hydride produces the corresponding 4-(phenylamino)-1,2-dihydroquinolines 26 (R(1) = alkyl) or 4-(phenylimino)-1,2,3,4-tetrahydroquinolines 27 and 38 (R = Ph), depending on the nature of the substituents at C-3 and the workup conditions.

  DOI：

  10.1021/jo00128a041

文献信息

• METHODS FOR TREATING SCHIZOPHRENIA
  申请人：Lichter Jay

  公开号：US20120184547A1

  公开（公告）日：2012-07-19

  Provided herein are PAK inhibitors. Also provided herein are compositions and methods for treating an individual suffering from schizophrenia.

  提供PAK抑制剂。此外，还提供了用于治疗患有精神分裂症的个体的组合物和方法。
• METHODS FOR TREATING NEUROLOGICAL CONDITIONS
  申请人：Lichter Jay

  公开号：US20130225575A1

  公开（公告）日：2013-08-29

  Provided herein are PAK inhibitors. Also provided herein are compositions and methods for treating an individual suffering from certain neurological conditions.

  本文提供了PAK抑制剂。同时提供了用于治疗患有某些神经疾病的个体的组合物和方法。
• A Versatile Method for the Preparation of Substituted 1,2,3,4-Tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00128a041

  日期：1995.11

  N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 1 react with acetaldehyde to give 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 11 in good yields along with minor amounts of diamines 12. Reactions of 1 with higher enolizable aldehydes R(1)CH(2)CHO lead to 4-(benzotriazol-1-yl)tetrahydroquinolines with an R(1) substituent at C-3 (17, 18). Condensation of N-methylaniline with two molecules of aldehyde RCH(2)CHO and one molecule of benzotriazole produces 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 34 bearing an R substituent at C-3 and RCH(2) on C-2. In all of these products, the benzotriazol-1-yl moiety can be replaced by a hydrogen atom (by reduction with lithium aluminum hydride) or by an alkyl or aryl group (by reaction with a Grignard reagent). Treatment of 11 with sodium alkoxides leads to 4-alkoxy-1,2,3,4-tetrahydroquinolines 10. Elimination of a molecule of nitrogen from the benzotriazole system of 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 17, 18, and 35 by sodium hydride produces the corresponding 4-(phenylamino)-1,2-dihydroquinolines 26 (R(1) = alkyl) or 4-(phenylimino)-1,2,3,4-tetrahydroquinolines 27 and 38 (R = Ph), depending on the nature of the substituents at C-3 and the workup conditions.