(2R,4R)-2-methyl-1,2,3,4-tetrahydroquinoline-4-ol

• 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
• 英文名称: (2R,4R)-2-methyl-1,2,3,4-tetrahydroquinoline-4-ol
• 英文别名: (2R,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-ol
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: IFQVLAITGJIHRS-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基喹啉 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium formate 、 (1R,2R)-(-)-N-(对甲基苯磺酰基)-1,2-二苯基乙二胺 作用下， 以 aq. acetate buffer 为溶剂， 反应 36.0h， 以47%的产率得到(2R,4R)-2-methyl-1,2,3,4-tetrahydroquinoline-4-ol
  参考文献：
  名称：

  Asymmetric combinational “metal-biocatalytic system”: One approach to chiral 2-subsituted-tetrahydroquinoline-4-ols towards two-step one-pot processes in aqueous media

  摘要：

  A novel asymmetric "metal-biocatalytic system", involving Rh-catalyzed asymmetric transfer hydrogenation and whole cell mediated asymmetric hydroxylation in aqueous buffer, has been achieved. The methodology gives access to 2-subsituted-tetrahydroquinoline-4-ols bearing two stereocenters from 2-subsituted-quinolines in moderate to excellent results (up to 47% yield, 99:1 dr, and >99% ee). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.04.074

文献信息

• Enantioselective synthesis of 1,2,3,4-tetrahydroquinoline-4-ols and 2,3-dihydroquinolin-4(1H)-ones via a sequential asymmetric hydroxylation/diastereoselective oxidation process using Rhodococcus equi ZMU-LK19
  作者：Ke Li、Juxiang Wang、Kailin Wu、Daijun Zheng、Xiaojian Zhou、Wenyong Han、Nanwei Wan、Baodong Cui、Yongzheng Chen

  DOI：10.1039/c7ob00151g

  日期：——

  A cascade biocatalysis system containing asymmetric hydroxylation and diastereoselective oxidation was developed using Rhodococcus equi ZMU-LK19, which gave chiral 2-substituted-1,2,3,4-tetrahydroquinoline-4-ols (2) (up to 57% isolated yield, 99:1 dr, and >99%...

  使用马生红球菌ZMU-LK19开发了一种包含不对称羟基化和非对映选择性氧化的级联生物催化系统，该系统可得到手性2-取代-1,2,3,4-四氢喹啉-4-醇（2）（分离产率高达57％， 99：1博士，> 99％...
• CAN-catalyzed three-component reaction between anilines and alkyl vinyl ethers: stereoselective synthesis of 2-methyl-1,2,3,4-tetrahydroquinolines and studies on their aromatization
  作者：Vellaisamy Sridharan、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1016/j.tet.2006.11.002

  日期：2007.1

  The CAN-catalyzed reaction between anilines and vinyl ethers at room temperature provides a convenient and efficient access to 4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines. This reaction is stereoselective, favouring a cis arrangements for the alkoxy and methyl groups, and involves a three-component process that leaves a molecule of alcohol as the only side product. 2-Methylquinoline derivatives were efficiently prepared from 4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines by Pd-C-promoted dehydrogenation. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric combinational “metal-biocatalytic system”: One approach to chiral 2-subsituted-tetrahydroquinoline-4-ols towards two-step one-pot processes in aqueous media
  作者：Juxiang Wang、Ke Li、Xiaojian Zhou、Wenyong Han、Nanwei Wan、Baodong Cui、Huihui Wang、Weicheng Yuan、Yongzheng Chen

  DOI：10.1016/j.tetlet.2017.04.074

  日期：2017.6

  A novel asymmetric "metal-biocatalytic system", involving Rh-catalyzed asymmetric transfer hydrogenation and whole cell mediated asymmetric hydroxylation in aqueous buffer, has been achieved. The methodology gives access to 2-subsituted-tetrahydroquinoline-4-ols bearing two stereocenters from 2-subsituted-quinolines in moderate to excellent results (up to 47% yield, 99:1 dr, and >99% ee). (C) 2017 Elsevier Ltd. All rights reserved.