7-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline | 72105-98-7

• 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: 7-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 72105-98-7
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: RQVDQPKNWIVQDU-UHFFFAOYSA-N

物化性质

• 沸点：
  352.2±11.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  7-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline 在 N,N-二甲基甲酰胺 作用下， 反应 24.0h， 以75%的产率得到7-methyl-1-phenyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  溶剂促进的四氢异喹啉在没有催化剂和氢受体的情况下高度选择性的脱氢

  摘要：

  描述了一种不寻常的溶剂DMF促进的1-取代的1,2,3,4-四氢异喹啉脱氢反应，合成环亚胺。这种对环境友好的反应不需要任何金属催化剂，氧化剂或氢受体。可以以良好的产率和优异的化学选择性获得各种结构变化的3，4-二氢异喹啉。

  DOI：

  10.1016/j.tetlet.2016.01.008
• 作为产物：
  描述：

  7-methyl-1-phenyl-3,4-dihydroisoquinoline 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.0h， 以79%的产率得到7-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  氨基甲酸酯活化率的提高使得能够合成四环苯并内酰胺：8-氧代berbines及其5和7元C环同系物

  摘要：

  开发了直接酰胺化芳族环系N-氨基甲酰基四氢异喹啉底物的途径。该途径使人们能够普遍获得8-氧小ber碱及其5和7元C环同系物。它克服了导致异喹啉主链破坏的不希望的串联副反应，这种副反应在我们先前报道的超酸性氨基甲酸酯活化方法下不可避免地发生。

  DOI：

  10.1039/d0ob02096f

文献信息

• Substituted 4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-4-oxobutyric acid amide as KCNQ2/3 modulators
  申请人：Kühnert Sven

  公开号：US20100152234A1

  公开（公告）日：2010-06-17

  The invention relates to substituted tetrahydroisoquinolinyl-4-oxobutyric acid amides, methods for the preparation thereof, medicinal products containing these compounds and the use of these compounds for the preparation of medicinal products.

  这项发明涉及替代的四氢异喹啉基-4-氧基丁酸酰胺，其制备方法，含有这些化合物的药物产品以及利用这些化合物制备药物产品的用途。
• Substituted 4-(1.2,3,4-tetrahydroisoquinolin-2-yl)-4-oxobutyric acid amide as KCNQ2/3 modulators
  申请人：Kühnert Sven

  公开号：US08367700B2

  公开（公告）日：2013-02-05

  The invention relates to substituted tetrahydroisoquinolinyl-4-oxobutyric acid amides, methods for the preparation thereof, medicinal products containing these compounds and the use of these compounds for the preparation of medicinal products.

  本发明涉及取代的四氢异喹啉基-4-氧代丁酰胺，其制备方法，含有这些化合物的药物产品以及使用这些化合物制备药物产品的用途。
• Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C
  作者：Yue Ji、Mu-Wang Chen、Lei Shi、Yong-Gui Zhou

  DOI：10.1016/s1872-2067(14)60243-6

  日期：2015.1

  A highly selective procedure has been developed for the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines over K3PO4 center dot 3H(2)O-modified Pd/C catalyst. This new method provides facile, atom-economical and environmentally friendly access to 1-substituted-3,4-dihydroisoquinolines without the need for stoichiometric amounts of harmful oxidants. The use of standard Pd/C as a catalyst for this process gave poor chemoselectivity. Pleasingly, the use of a K3PO4 center dot 3H(2)O-modified Pd/C catalyst promoted the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines with excellent chemoselectivity by suppressing further dehydroaromatization. Furthermore, conducting the reaction under an atmosphere of oxygen led to further improvements in the chemoselectivity of the dehydrogenation, with the ratio of imine to isoquinoline reaching up to 32/1. The heterogenous Pd/C catalyst could also be recycled and reused at least three times with excellent conversion and chemoselectivity, demonstrating the significantly practical potential of this methodology. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
• Concise Redox Deracemization of Secondary and Tertiary Amines with a Tetrahydroisoquinoline Core via a Nonenzymatic Process
  作者：Yue Ji、Lei Shi、Mu-Wang Chen、Guang-Shou Feng、Yong-Gui Zhou

  DOI：10.1021/jacs.5b06659

  日期：2015.8.26

  A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridum-catalyzed asymmetric hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.
• SUBSTITUIERTE 4-(1,2,3,4-TETRAHYDROISOCHINOLIN-2-YL)-4-OXO-BUTTERSÄUREAMIDE ALS KCNQ2/3 MODULATOREN
  申请人：Grünenthal GmbH

  公开号：EP2358681A1

  公开（公告）日：2011-08-24