(S)-6,7-dimethoxy-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline | 1068158-43-9

• 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: (S)-6,7-dimethoxy-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6,7-dimethoxy-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline；(1S)-1-cyclohexyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 1068158-43-9
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: WCIGAVRPVAPXAG-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-cyclohexyl-3,4-dihydro-6,7-dimethoxyisoquinoline 在 silver hexafluoroantimonate 、 C₃₁H₃₆ClN₂O₂RhS 、 氢气 作用下， 以 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 反应 4.0h， 以94%的产率得到(S)-6,7-dimethoxy-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Asymmetric Hydrogenation of Cyclic Imines with an Ionic Cp*Rh(III) Catalyst

  摘要：

  When associated with a noncoordinating bulky conunteranion, a cationic Cp*Rh(III)-diamine catalyst displayed excellent enantioselectivities in asymmetric hydrogenation of cyclic imines, affording bioactive tetrahydroisoquinolines and tetrahydro-beta-carbolines frequently with 99% ee's.

  DOI：

  10.1021/ja8050958

文献信息

• Highly Enantioselective Synthesis of Chiral Tetrahydroquinolines and Tetrahydroisoquinolines by Ruthenium‐Catalyzed Asymmetric Hydrogenation in Ionic Liquid
  作者：Zi‐Yuan Ding、Tianli Wang、Yan‐Mei He、Fei Chen、Hai‐Feng Zhou、Qing‐Hua Fan、Qingxiang Guo、Albert S. C. Chan

  DOI：10.1002/adsc.201300698

  日期：2013.12.16

  AbstractAsymmetric hydrogenation reactions of quinolines and 3,4‐dihydroisoquinolines using the chiral cationic ruthenium complex Ru(TsDPEN) [TsDPEN=N‐(p‐toluenesulfonyl)‐1,2‐diphenylethylenediamine] as catalyst in neat imidazolium ionic liquids have been investigated. The catalytic performance was influenced by the anion of the ionic liquids for both substrate classes. A range of 2‐alkyl‐substituted 1,2,3,4‐tetrahydroquinolines and 1‐alkyl‐substituted 1,2,3,4‐tetrahydroisoquinolines was obtained in high yields with up to >99% ee. Interestingly, the hydrogenation of quinoline derivatives bearing a carbonyl group was selective for the CN (quinoline) over the CO (ketone) bonds, while such a unique chemoselectivity was not observed in methanol. Furthermore, the ruthenium catalysts could be easily recycled at least 5 times in the asymmetric hydrogenation of 3,4‐dihydroisoquinoline by solvent extraction. To further facilitate the recovery of catalyst and reduce the use of organic solvent, a thin film of ionic liquid containing Ru(TsDPEN) was supported on silica gels. This supported ionic liquid‐phase catalyst was effective in the asymmetric hydrogenation of quinoline, and could be recycled at least 6 times by simple filtration.magnified image