5-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene | 27164-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene
• 英文别名: 1-chloro-2,3-dimethoxy-5-(2-nitroethenyl)benzene
• CAS: 27164-13-2
• 化学式: C₁₀H₁₀ClNO₄
• 分子量: 243.647
• InChiKey: AYULBTLOYLJHSB-UHFFFAOYSA-N

物化性质

• 沸点：
  378.7±42.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene 在 盐酸 、 锌 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以87%的产率得到2-氯-3,4-二甲氧基苯乙胺
  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
• 作为产物：
  描述：

  5-氯香草醛 在 ammonium acetate 、 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 13.0h， 生成 5-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene
  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

• Hellot,J.-P. et al., Chimica Therapeutica, 1970, vol. 5, p. 55 - 64
  作者：Hellot,J.-P. et al.

  DOI：——

  日期：——
• 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.