1-Benzo[1,3]dioxol-5-ylmethyl-6,7-dimethoxy-isoquinoline-3-carboxylic acid methyl ester | 1046475-63-1

• 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-Benzo[1,3]dioxol-5-ylmethyl-6,7-dimethoxy-isoquinoline-3-carboxylic acid methyl ester
• 英文别名: Methyl 1-(1,3-benzodioxol-5-ylmethyl)-6,7-dimethoxyisoquinoline-3-carboxylate
• CAS: 1046475-63-1
• 化学式: C₂₁H₁₉NO₆
• 分子量: 381.385
• InChiKey: ASRTZUUUROWFOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-Benzo[1,3]dioxol-5-ylmethyl-6,7-dimethoxy-isoquinoline-3-carboxylic acid methyl ester 在 selenium(IV) oxide 、 溶剂黄146 作用下， 生成 1-(Benzo[1,3]dioxole-5-carbonyl)-6,7-dimethoxy-isoquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  6,7-Dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-Like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain

  摘要：

  A series of 1-benzoyl isoquinolines, based on compound 1, was synthesized and evaluated for their ability to displace IGF-I from its complex with IGF-binding protein-3. Successful modifications of I included the replacement of the 3,4-dihydroxy-benzoyl group with a substituted benzyl group. These alternations culminated in the discovery of compounds such as 7o which had excellent in vitro potency (K-i = 9.4 nM) but with one less of the labile catechol functionality of 1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00321-4
• 作为产物：
  描述：

  1-Benzo[1,3]dioxol-5-ylmethyl-6,7-dimethoxy-3,4-dihydro-isoquinoline-3-carboxylic acid methyl ester 在 sulfur 作用下， 生成 1-Benzo[1,3]dioxol-5-ylmethyl-6,7-dimethoxy-isoquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  6,7-Dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-Like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain

  摘要：

  A series of 1-benzoyl isoquinolines, based on compound 1, was synthesized and evaluated for their ability to displace IGF-I from its complex with IGF-binding protein-3. Successful modifications of I included the replacement of the 3,4-dihydroxy-benzoyl group with a substituted benzyl group. These alternations culminated in the discovery of compounds such as 7o which had excellent in vitro potency (K-i = 9.4 nM) but with one less of the labile catechol functionality of 1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00321-4

文献信息

• Synthesis of Isoquinoline-3-Carboxylates and Benzocyclobutanes via Reaction of 2-Amidoacrylate Esters with Arynes
  作者：Yeeman Ramtohul、Tom Blackburn

  DOI：10.1055/s-2008-1072723

  日期：2008.5

  A mild and general method for the synthesis of a variety of 2-substituted isoquinoline 3-carboxylates and benzocyclobutanes from the reaction of 2-amidoacrylate esters with arynes has been developed.

  已开发出一种温和且通用的方法，通过将2-酰胺丙烯酸酯与芳杂烯反应，合成多种2取代的异喹啉-3-羧酸酯和苯并环丁烷。