(S)-3-苄基-1,2,3,4-四氢喹啉 | 37045-17-3

• 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
• 中文名称: (S)-3-苄基-1,2,3,4-四氢喹啉
• 英文名称: (S)-3-benzyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 3-benzyl-1,2,3,4-tetrahydroquinoline；3-benzyl-1,2,3,4-tetrahydro-quinoline；3-Benzyl-1,2,3,4-tetrahydro-chinolin；1,2,3,4-Tetrahydro-3-benzylquinoline
• CAS: 37045-17-3
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: AQFUPZFWRXHCAN-UHFFFAOYSA-N

物化性质

• 熔点：
  80.5-81.5 °C
• 沸点：
  184-187 °C(Press: 3 Torr)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-苄基-1,2,3,4-四氢喹啉 在 Pd-BaSO₄ 作用下， 生成 3-benzylquinoline
  参考文献：
  名称：

  Reduction and Benzylation by Means of Benzyl Alcohol. III. Experiments in the Pyridine Series¹

  摘要：

  DOI：

  10.1021/ja01597a063
• 作为产物：
  描述：

  3-benzyl-3,4-dihydroquinolin-2(1H)-one 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 以67 mg的产率得到(S)-3-苄基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  Enantioselective Annulations for Dihydroquinolones by in Situ Generation of Azolium Enolates

  摘要：

  A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.

  DOI：

  10.1021/ja505880r

文献信息

• Ionic diamine rhodium complex catalyzed hydroaminomethylation of 2-allylanilines
  作者：Kazumi Okuro、Howard Alper

  DOI：10.1016/j.tetlet.2010.07.048

  日期：2010.9

  Ionic diamine rhodium complexes catalyze the hydroaminomethylation of 2-allylanilines. The reaction involves initial hydroformylation followed by reductive amination, which provides direct access to 1,2,3,4-tetrahydroquinolines and 2,3,4,5-1H-1-benzazepines. (C) 2010 Elsevier Ltd. All rights reserved.
• Reduction and Benzylation by Means of Benzyl Alcohol. III. Experiments in the Pyridine Series¹
  作者：Moshe Avramoff、Yaër Sprinzak

  DOI：10.1021/ja01597a063

  日期：1956.8
• Enantioselective Annulations for Dihydroquinolones by in Situ Generation of Azolium Enolates
  作者：Anna Lee、Ashkaan Younai、Christopher K. Price、Javier Izquierdo、Rama K. Mishra、Karl A. Scheidt

  DOI：10.1021/ja505880r

  日期：2014.7.30

  A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.