N-ethyl-2-chlorodopamine | 102851-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-ethyl-2-chlorodopamine
• 英文别名: 3-Chloro-4-[2-(ethylamino)ethyl]benzene-1,2-diol
• CAS: 102851-72-9
• 化学式: C₁₀H₁₄ClNO₂
• 分子量: 215.68
• InChiKey: JLIPDGUALDIARD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-1-(氯甲基)-3,4-二甲氧基苯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 碘代三甲硅烷 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 环丁砜 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 251.0h， 生成 N-ethyl-2-chlorodopamine
  参考文献：
  名称：

  Synthesis and renal vasodilator activity of 2-chlorodopamine and N-substituted derivatives

  摘要：

  A four-step synthesis of 2-chlorodopamine (2b) is presented as well as methods for the syntheses of the N-methyl, ethyl, and n-propyl analogues (2c-e). Compounds 2b and 2c were essentially equipotent to dopamine for increasing renal blood flow in anesthetized dogs that had been treated with the alpha-adrenergic antagonist phenoxybenzamine. The increases in renal blood flow were blocked by the DA1 antagonist (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. Compounds 2d and 2e were significantly less potent than dopamine in the same model; the increases in renal blood flow were attenuated by propranolol and blocked by a combination of propranolol and (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. The significance of an o-chloro substituent on dopamine analogues for the activation of the DA1 receptor is briefly discussed.

  DOI：

  10.1021/jm00159a005

文献信息

• Synthesis and renal vasodilator activity of 2-chlorodopamine and N-substituted derivatives
  作者：James R. McCarthy、Jefferson McCowan、Mark B. Zimmerman、Marcia A. Wenger、Lee W. Emmert

  DOI：10.1021/jm00159a005

  日期：1986.9

  A four-step synthesis of 2-chlorodopamine (2b) is presented as well as methods for the syntheses of the N-methyl, ethyl, and n-propyl analogues (2c-e). Compounds 2b and 2c were essentially equipotent to dopamine for increasing renal blood flow in anesthetized dogs that had been treated with the alpha-adrenergic antagonist phenoxybenzamine. The increases in renal blood flow were blocked by the DA1 antagonist (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. Compounds 2d and 2e were significantly less potent than dopamine in the same model; the increases in renal blood flow were attenuated by propranolol and blocked by a combination of propranolol and (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. The significance of an o-chloro substituent on dopamine analogues for the activation of the DA1 receptor is briefly discussed.