(R)-1-(3-bromophenyl)-2-tosyl-1,2,3,4-tetrahydroisoquinoline | 1381986-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (R)-1-(3-bromophenyl)-2-tosyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (1R)-1-(3-bromophenyl)-2-(4-methylphenyl)sulfonyl-3,4-dihydro-1H-isoquinoline
• CAS: 1381986-36-2
• 化学式: C₂₂H₂₀BrNO₂S
• 分子量: 442.376
• InChiKey: CVKKJRSYMYJCBA-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(3-溴苯基)-3,4-二氢异喹啉 、 对甲苯磺酰氯 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 (R)-3,5-diMe-Synphos 、 氢气 、 1,8-双二甲氨基萘 作用下， 以 1,4-二氧六环 为溶剂， 40.0 ℃ 、1.0 MPa 条件下， 反应 18.0h， 生成 (R)-1-(3-bromophenyl)-2-tosyl-1,2,3,4-tetrahydroisoquinoline 、 (S)-1-(3-bromophenyl)-2-tosyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Enantioselective Synthesis of 1-Aryl-tetrahydroisoquinolines through Iridium Catalyzed Asymmetric Hydrogenation

  摘要：

  Asymmetric hydrogenation of 1-aryl-3,4-dihydrolsoquinolines using the [IrCODCl](2)/(R)-3,5-diMe-Synphos catalyst is reported. Under mild reaction conditions, this atom-economical process provides easy access to a variety of enantioenriched 1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives, which are important pharmacophores found in several pharmaceutical drug candidates, in high yields and enantiomeric excesses up to 99% after a single crystallization.

  DOI：

  10.1021/ol301281s

文献信息

• Enantioselective Synthesis of 1-Aryl-tetrahydroisoquinolines through Iridium Catalyzed Asymmetric Hydrogenation
  作者：Farouk Berhal、Zi Wu、Zhaoguo Zhang、Tahar Ayad、Virginie Ratovelomanana-Vidal

  DOI：10.1021/ol301281s

  日期：2012.7.6

  Asymmetric hydrogenation of 1-aryl-3,4-dihydrolsoquinolines using the [IrCODCl](2)/(R)-3,5-diMe-Synphos catalyst is reported. Under mild reaction conditions, this atom-economical process provides easy access to a variety of enantioenriched 1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives, which are important pharmacophores found in several pharmaceutical drug candidates, in high yields and enantiomeric excesses up to 99% after a single crystallization.