6,7-dimethoxy-4-(2-hydroxy-ethyl)-3-(3,4-methylenedioxyphenyl)-isoquinoline | 912649-13-9

• 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: 6,7-dimethoxy-4-(2-hydroxy-ethyl)-3-(3,4-methylenedioxyphenyl)-isoquinoline
• 英文别名: 2-[3-(1,3-Benzodioxol-5-yl)-6,7-dimethoxyisoquinolin-4-yl]ethanol
• CAS: 912649-13-9
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: ALYBNAFSTOOIRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-4-(2-hydroxy-ethyl)-3-(3,4-methylenedioxyphenyl)-isoquinoline 在 草酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 以77%的产率得到6,7-dimethoxy-4-(2-oxo-ethyl)-3-(3,4-methylenedioxyphenyl)-isoquinoline
  参考文献：
  名称：

  A concise synthesis of nornitidine via nickel- or palladium-catalyzed annulation

  摘要：

  A concise method to synthesize benzo[c]phenanthridine alkaloid, nornitidine, was developed utilizing nickel- or palladium-catalyzed iminoannulation of an internal alkyne. The advantages of this strategy included readily available starting materials, inexpensive reagents, short reaction steps, and good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.048
• 作为产物：
  描述：

  6-溴藜芦醛 在 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 锌 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 6,7-dimethoxy-4-(2-hydroxy-ethyl)-3-(3,4-methylenedioxyphenyl)-isoquinoline
  参考文献：
  名称：

  A concise synthesis of nornitidine via nickel- or palladium-catalyzed annulation

  摘要：

  A concise method to synthesize benzo[c]phenanthridine alkaloid, nornitidine, was developed utilizing nickel- or palladium-catalyzed iminoannulation of an internal alkyne. The advantages of this strategy included readily available starting materials, inexpensive reagents, short reaction steps, and good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.048

文献信息

• Short synthesis and antimalarial activity of fagaronine
  作者：M. Rivaud、A. Mendoza、M. Sauvain、A. Valentin、V. Jullian

  DOI：10.1016/j.bmc.2012.05.061

  日期：2012.8

  Herein, we report a new synthesis of fagaronine 1, inspired by the synthesis reported by Luo for nornitidine. The in vitro biological activity of fagaronine against malaria on several chloroquine-sensitive and resistant Plasmodium falciparum strains was confirmed, and the selectivity index compared to mammalian cells was calculated. Fagaronine was found to have very good antimalarial activity in vivo, comparable to the activity of the reference compound chloroquine. Therefore, fagaronine appears to be a good potential lead for the design of new antimalarial molecules. (C) 2012 Elsevier Ltd. All rights reserved.
• A concise synthesis of nornitidine via nickel- or palladium-catalyzed annulation
  作者：Yu Luo、Yuhua Mei、Jianbo Zhang、Wei Lu、Jie Tang

  DOI：10.1016/j.tet.2006.07.048

  日期：2006.9

  A concise method to synthesize benzo[c]phenanthridine alkaloid, nornitidine, was developed utilizing nickel- or palladium-catalyzed iminoannulation of an internal alkyne. The advantages of this strategy included readily available starting materials, inexpensive reagents, short reaction steps, and good yields. (c) 2006 Elsevier Ltd. All rights reserved.