1-(2-iodo-4,5-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline | 286441-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(2-iodo-4,5-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline
• 英文别名: 1-[(2-Iodo-4,5-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline
• CAS: 286441-18-7
• 化学式: C₂₀H₂₂INO₄
• 分子量: 467.303
• InChiKey: WOEKJXVEONCNSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-iodo-4,5-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以95%的产率得到5,6-Dihydro-2,3,9,10-tetramethoxy-indolo<2,1-a>isoquinoline
  参考文献：
  名称：

  A Facile Route to Indolo[2,1-a]isoquinolines and Dibenzopyrrocoline Alkaloids

  摘要：

  Treatment of 1-(2'-bromobenzyl)-3,4-dihydroisoquinolines 2 in the presence of K2CO3 in boiling DMF efficiently provided a variety of alkoxy-substituted indolo[2,1-a]isoquinolines 3. Application of this cyclization to 7-benzyloxyisoquinoline derivatives, followed by further elaboration of the resultant 2-benzyloxy-5,6-dihydroindolo[2,1-a]isoquinolines 16a,b, led to the formal synthesis of dibenzopyrrocoline alkaloids, (+/-)-cryptaustoline (1a) and (+/-)-cryptowoline (1b).

  DOI：

  10.1021/ol005802d
• 作为产物：
  描述：

  N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(2-iodo-4,5-dimethoxyphenyl)acetamide 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(2-iodo-4,5-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline
  参考文献：
  名称：

  The synthesis of 2′,2′-bis-benzylisoquinolines and their cytostatic activities

  摘要：

  The novel laudanosine dimers in which two laudanosine units are linked via a C-2 ' biaryl bond have been prepared by a sequence that involves formation of the biaryl bond first and then formation of the isoquinoline rings. Two of these compounds showed higher cytostatic activity on three cancer cell lines than thalicarpine. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.083

文献信息

• A Facile Route to Indolo[2,1-<i>a</i>]isoquinolines and Dibenzopyrrocoline Alkaloids
  作者：Kazuhiko Orito、Rika Harada、Shiho Uchiito、Masao Tokuda

  DOI：10.1021/ol005802d

  日期：2000.6.1

  Treatment of 1-(2'-bromobenzyl)-3,4-dihydroisoquinolines 2 in the presence of K2CO3 in boiling DMF efficiently provided a variety of alkoxy-substituted indolo[2,1-a]isoquinolines 3. Application of this cyclization to 7-benzyloxyisoquinoline derivatives, followed by further elaboration of the resultant 2-benzyloxy-5,6-dihydroindolo[2,1-a]isoquinolines 16a,b, led to the formal synthesis of dibenzopyrrocoline alkaloids, (+/-)-cryptaustoline (1a) and (+/-)-cryptowoline (1b).
• The synthesis of 2′,2′-bis-benzylisoquinolines and their cytostatic activities
  作者：Stephen R. Taylor、Alison T. Ung、Stephen G. Pyne

  DOI：10.1016/j.tet.2007.08.083

  日期：2007.11

  The novel laudanosine dimers in which two laudanosine units are linked via a C-2 ' biaryl bond have been prepared by a sequence that involves formation of the biaryl bond first and then formation of the isoquinoline rings. Two of these compounds showed higher cytostatic activity on three cancer cell lines than thalicarpine. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.