5-chlorodopamine | 116653-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-chlorodopamine
• 英文别名: 5-(2-Aminoethyl)-3-chlorobenzene-1,2-diol；5-(2-aminoethyl)-3-chlorobenzene-1,2-diol
• CAS: 116653-25-9
• 化学式: C₈H₁₀ClNO₂
• 分子量: 187.626
• InChiKey: LOHZNVBFLUDIHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene 在 盐酸 、 三溴化硼 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-chlorodopamine
  参考文献：
  名称：

  Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues

  摘要：

  A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 degrees C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.

  DOI：

  10.1055/s-0034-1379481

文献信息

• Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues
  作者：Justin Maresh、Arthur Ralko、Tom Speltz、James Burke、Casey Murphy、Zachary Gaskell、JoAnn Girel、Erin Terranova、Conrad Richtscheidt、Mark Krzeszowiec

  DOI：10.1055/s-0034-1379481

  日期：——

  A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 degrees C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.