(R)-7-bromo-2-phenyl-1,2,3,4-tetrahydroquinoxaline | 1221687-18-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-7-bromo-2-phenyl-1,2,3,4-tetrahydroquinoxaline
• 英文别名: (2R)-7-bromo-2-phenyl-1,2,3,4-tetrahydroquinoxaline
• CAS: 1221687-18-8
• 化学式: C₁₄H₁₃BrN₂
• 分子量: 289.175
• InChiKey: WMJKBEQPIFQNDX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-bromo-2-phenylquinoxaline 在 (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl phosphate 、 二氢吡啶 作用下， 以 氯仿 为溶剂， 以53%的产率得到(R)-7-bromo-2-phenyl-1,2,3,4-tetrahydroquinoxaline
  参考文献：
  名称：

  Continuous-flow catalytic asymmetric hydrogenations: Reaction optimization using FTIR inline analysis

  摘要：

  已经开发了在连续流微反应器中对苯并噁嗪、喹啉、喹啉和3- H-吲哚的不对称有机催化氢化反应。通过使用内联ReactIR流动池进行反应监测，可以快速方便地优化反应参数。还原反应进行顺利，并且所需产物以高收率和优异的对映选择性分离。

  DOI：

  10.3762/bjoc.8.32

文献信息

• The First General, Efficient and Highly Enantioselective Reduction of Quinoxalines and Quinoxalinones
  作者：Magnus Rueping、Francisco Tato、Fenja. R. Schoepke

  DOI：10.1002/chem.200902907

  日期：——

  Simple yet efficient: A series of diverse substituted tetrahydroquinoxalines and dihydroquinoxalinones have been synthesized for the first time in a highly enantioselective fashion (see scheme). Using this metal‐free hydrogenation it is possible to isolate these products, which are of high pharmaceutical interest, in good yields and with excellent enantioselectivities in a minimal number of reaction

  简单而有效：首次以高度对映选择性的方式合成了一系列多样的取代的四氢喹喔啉和二氢喹喔啉（参见方案）。使用这种无金属的氢化反应，可以在最少的反应步骤中分离出具有高度药用价值，高收率和出色对映选择性的这些产物。
• Asymmetric Organocatalytic Tandem Cyclization/Transfer Hydrogenation: A Synthetic Strategy for Enantioenriched Nitrogen Heterocycles
  作者：Feng Shi、Wei Tan、Hong‐Hao Zhang、Mei Li、Qin Ye、Guan‐Hua Ma、Shu‐Jiang Tu、Guigen Li

  DOI：10.1002/adsc.201300576

  日期：2013.12.16

  AbstractAn asymmetric organocatalytic tandem reaction comprising cyclization/transfer hydrogenation has been established in a compatible and synergistic way, leading to the step‐economical synthesis of enantioenriched tetrahydroquinoxalines and dihydroquinoxalinones from readily accessible materials in excellent enantioselectivity of up to >99% ee. This protocol of a one‐operation tandem reaction combines the merits of both tandem reactions and asymmetric organocatalysis, providing an efficient strategy for concisely and enantioselectively synthesizing nitrogen heterocycles with biological relevance.magnified image
• Continuous-flow catalytic asymmetric hydrogenations: Reaction optimization using FTIR inline analysis
  作者：Magnus Rueping、Teerawut Bootwicha、Erli Sugiono

  DOI：10.3762/bjoc.8.32

  日期：——

  The asymmetric organocatalytic hydrogenation of benzoxazines, quinolines, quinoxalines and 3H-indoles in continuous-flow microreactors has been developed. Reaction monitoring was achieved by using an inline ReactIR flow cell, which allows fast and convenient optimization of reaction parameters. The reductions proceeded well, and the desired products were isolated in high yields and with excellent enantioselectivities.

  已经开发了在连续流微反应器中对苯并噁嗪、喹啉、喹啉和3- H-吲哚的不对称有机催化氢化反应。通过使用内联ReactIR流动池进行反应监测，可以快速方便地优化反应参数。还原反应进行顺利，并且所需产物以高收率和优异的对映选择性分离。