1-(3-chloro-4-methoxyphenyl)-2-aminoethanol | 778536-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-chloro-4-methoxyphenyl)-2-aminoethanol
• 英文别名: 2-Amino-1-(3-chloro-4-methoxyphenyl)ethan-1-ol；2-amino-1-(3-chloro-4-methoxyphenyl)ethanol
• CAS: 778536-58-6
• 化学式: C₉H₁₂ClNO₂
• 分子量: 201.653
• InChiKey: FNZGVRAIYSDTRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  359.0±42.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-4-iodo-1H-pyridin-2-one 、 1-(3-chloro-4-methoxyphenyl)-2-aminoethanol 以 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-4-[2-(3-chloro-4-methoxy-phenyl)-2-hydroxy-ethylamino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one
  参考文献：
  名称：

  Novel 1H-(benzimidazol-2-yl)-1H-pyridin-2-one inhibitors of insulin-like growth factor I (IGF-1R) kinase

  摘要：

  A novel class of 1H-(benzimidazol-2-yl)-1H-pyridin-2-one inhibitors of insulin-like growth factor I (IGF-1R) kinase is described. This report discusses the SAR of 4-(2-hydroxy-2-phenylethylamino)-substituted pyridones with improved IGF-1R potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.041
• 作为产物：
  描述：

  3-氯-4-羟基苯甲酸 在 manganese(IV) oxide 、 sodium hydroxide 、 硫酸 、 硼烷 、 potassium carbonate 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 50.0h， 生成 1-(3-chloro-4-methoxyphenyl)-2-aminoethanol
  参考文献：
  名称：

  Evaluation of isomeric 4-(chlorohydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines as dopamine D-1 antagonists

  摘要：

  The isomeric 4-(3-chloro-4-hydroxyphenyl)- and 4-(4-chloro-3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines, the N-methyl derivative of the 4-(4-chloro-3-hydroxyphenyl) isomer, and 4-(3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline were synthesized and evaluated for dopamine D-1 antagonist activity. The 4-(3-chloro-4-hydroxyphenyl) and the 4-(3-hydroxyphenyl) isomer possessed similar potencies as D-1 antagonists. Introduction of the N-methyl group enhanced potency about twofold. The "pharmacophore" for selective dopamine D-1 antagonist activity appears to be a tertiary 2-(3-hydroxyphenyl)-2-phenethylamine.

  DOI：

  10.1021/jm00393a033

文献信息

• Evaluation of isomeric 4-(chlorohydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines as dopamine D-1 antagonists
  作者：Robert M. Riggs、David E. Nichols、Mark M. Foreman、Lewis L. Truex

  DOI：10.1021/jm00393a033

  日期：1987.10

  The isomeric 4-(3-chloro-4-hydroxyphenyl)- and 4-(4-chloro-3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines, the N-methyl derivative of the 4-(4-chloro-3-hydroxyphenyl) isomer, and 4-(3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline were synthesized and evaluated for dopamine D-1 antagonist activity. The 4-(3-chloro-4-hydroxyphenyl) and the 4-(3-hydroxyphenyl) isomer possessed similar potencies as D-1 antagonists. Introduction of the N-methyl group enhanced potency about twofold. The "pharmacophore" for selective dopamine D-1 antagonist activity appears to be a tertiary 2-(3-hydroxyphenyl)-2-phenethylamine.
• Novel 1H-(benzimidazol-2-yl)-1H-pyridin-2-one inhibitors of insulin-like growth factor I (IGF-1R) kinase
  作者：Mark D. Wittman、Balu Balasubramanian、Karen Stoffan、Upender Velaparthi、Pieying Liu、Subramaniam Krishnanathan、Joan Carboni、Aixin Li、Ann Greer、Ricardo Attar、Marco Gottardis、Chiehying Chang、Bruce Jacobson、Yax Sun、Steven Hansel、Mary Zoeckler、Dolatrai M. Vyas

  DOI：10.1016/j.bmcl.2006.11.041

  日期：2007.2

  A novel class of 1H-(benzimidazol-2-yl)-1H-pyridin-2-one inhibitors of insulin-like growth factor I (IGF-1R) kinase is described. This report discusses the SAR of 4-(2-hydroxy-2-phenylethylamino)-substituted pyridones with improved IGF-1R potency. (c) 2006 Elsevier Ltd. All rights reserved.