1-(2-iodophenyl)-3,4-dihydro-6,7-dimethoxyisoquinoline | 143600-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 1-(2-iodophenyl)-3,4-dihydro-6,7-dimethoxyisoquinoline
• 英文别名: 1-(2-Iodophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline；1-(2-iodophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline
• CAS: 143600-70-8
• 化学式: C₁₇H₁₆INO₂
• 分子量: 393.224
• InChiKey: FPSCMKVRGNGMEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-iodophenyl)-3,4-dihydro-6,7-dimethoxyisoquinoline 在 palladium on activated charcoal sodium thiosulfate 作用下， 以 水 、 苯 为溶剂， 反应 7.25h， 生成 5,6-dimethoxyindeno<1,2,3-i>isoquinoline
  参考文献：
  名称：

  Photocyclization of 1-(2-halophenyl)-3,4-dihydro-6,7-dimethoxyisoquinolines: a short and new synthesis of triclisine

  摘要：

  A short and new synthesis of the non-phenolic azafluoranthene alkaloid triclisine utilizing the photocyclization of 1-(2-halophenyl)-3,4-dihydro-6,7-dimethoxyisoquinolines as a key step has been described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.076
• 作为产物：
  描述：

  N-(3,4-dimethoxyphenethyl)-2-iodo benzamide 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 1-(2-iodophenyl)-3,4-dihydro-6,7-dimethoxyisoquinoline
  参考文献：
  名称：

  通过环亚胺-环酸酐反应制备的新型角取代[1,4]噻嗪并[3,4-a]异喹啉羧酸

  摘要：

  首次研究了1-芳基-3,4-二氢异喹啉与单环酸酐的反应。该方法是获得以前未知的具有反式构型的角芳基取代外消旋 [1,4] 噻嗪并 [3,4-a] 异喹啉衍生物的第一个单步路线。研究发现，起始 3,4-二氢异喹啉中芳基对位的吸电子取代基导致更高的产率和更短的反应时间，这与之前对高邻苯二甲酸酐和类似无环 N 反应的观察结果相反-芳基甲胺。

  DOI：

  10.1002/jhet.4601

文献信息

• Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation
  作者：Marc Perez、Zi Wu、Michelangelo Scalone、Tahar Ayad、Virginie Ratovelomanana-Vidal

  DOI：10.1002/ejoc.201500951

  日期：2015.9

  A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(η6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH–Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral

  使用 [RuIICl(η6-苯)TsDPEN] 配合物与 5:2 HCOOH-Et3N 共沸混合物作为氢源，方便且通用地对各种 1-芳基-3,4-二氢异喹啉衍生物进行不对称转移氢化已开发。在温和的反应条件下，所描述的催化转化确保了获得相应有价值的手性 1-芳基四氢异喹啉单元的实际合成途径，该单元具有高原子经济性、广泛的底物范围、高分离产率（高达 97%）和良好的对映选择性（高达99% ee)。发现反应的立体化学结果受催化剂结构和底物上存在的取代基的强烈影响。
• Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines: Access to Valuable Chiral 1-Aryl-Tetrahydroisoquinoline Scaffolds
  作者：Zi Wu、Marc Perez、Michelangelo Scalone、Tahar Ayad、Virginie Ratovelomanana-Vidal

  DOI：10.1002/anie.201301134

  日期：2013.4.26

  Give me an H! Give me another H! The first general and highly enantioselective Ru‐catalyzed transfer hydrogenation of a wide range of 1‐aryl‐substituted 1,2,3,4‐dihydroisoquinolines is described. This atom‐economic reaction proceeds under mild conditions, allowing rapid access to the corresponding biologically relevant 1‐aryl‐tetrahydroisoquinoline derivatives, in high yields and enantioselectivities

  给我一个H！再给我一个H！描述了第一个普通的和高对映选择性的Ru催化的广泛的1-芳基取代的1,2,3,4-二氢异喹啉的转移加氢反应。这种原子经济反应在温和的条件下进行，可以快速获得相应的生物学相关的1-芳基-四氢异喹啉衍生物，且收率高，对映选择性高达99％。
• Silver- and Gold-Mediated Intramolecular Cyclization to Substituted Tetracyclic Isoquinolizinium Hexafluorostilbates
  作者：Fang Liu、Xiao Ding、Lei Zhang、Yu Zhou、Linxiang Zhao、Hualiang Jiang、Hong Liu

  DOI：10.1021/jo1006174

  日期：2010.9.3

  A convenient route for the synthesis of various charged tetracyclic isoquinolizinium hexafluorostilbates was developed using AgSbF6/AuCl(PPh3) for the intramolecular addition of amine to alkyne. The described process is tolerant of a variety of functional groups and broadens the diversity of substrates with the use of 8-substituted tetracyclic isoquinolizinium salts.
• Photocyclization of 1-(2-halophenyl)-3,4-dihydro-6,7-dimethoxyisoquinolines: a short and new synthesis of triclisine
  作者：M.M.V. Ramana、R.H. Sharma、J.A. Parihar

  DOI：10.1016/j.tetlet.2005.04.076

  日期：2005.6

  A short and new synthesis of the non-phenolic azafluoranthene alkaloid triclisine utilizing the photocyclization of 1-(2-halophenyl)-3,4-dihydro-6,7-dimethoxyisoquinolines as a key step has been described. (c) 2005 Elsevier Ltd. All rights reserved.
• Novel angularly substituted [1,4]thiazino[3,4‐a]isoquinoline carboxylic acids prepared by cyclic imine‐cyclic anhydride reaction
  作者：Aleksandar Pashev、Nikola Burdzhiev、Elena Stanoeva

  DOI：10.1002/jhet.4601

  日期：2023.3

  The reaction between 1-aryl-3,4-dihydroisoquinolines and monocyclic anhydrides was studied for the first time. The method is the first one-step route to previously unknown angularly-aryl substituted racemic [1,4]thiazino[3,4-a]isoquinoline derivatives with trans configuration. It was found that electron-withdrawing substituents in the p-position of the aryl group in the starting 3,4-dihydroisoquinoline

  首次研究了1-芳基-3,4-二氢异喹啉与单环酸酐的反应。该方法是获得以前未知的具有反式构型的角芳基取代外消旋 [1,4] 噻嗪并 [3,4-a] 异喹啉衍生物的第一个单步路线。研究发现，起始 3,4-二氢异喹啉中芳基对位的吸电子取代基导致更高的产率和更短的反应时间，这与之前对高邻苯二甲酸酐和类似无环 N 反应的观察结果相反-芳基甲胺。