2-(2-chlorobenzylamino)-5-methylphenol

• 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: 2-(2-chlorobenzylamino)-5-methylphenol
• 英文别名: 2-[(2-chlorophenyl)methylamino]-5-methylphenol
• 化学式: C₁₄H₁₄ClNO
• 分子量: 247.724
• InChiKey: XKOAEGXWRBJALM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2-chlorobenzylamino)-5-methylphenol 在 potassium phosphate monohydrate 、 N,N-diisopropyl-2-(dicyclohexylphosphanyl)benzamide 、 水 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 4-(biphenyl-2-ylmethyl)-3,4-dihydro-2,7-dimethyl-3-oxo-2H-1,4-benzoxazine
  参考文献：
  名称：

  Increasing appendage diversity on 3,4-dihydro-3-oxo-2H-1,4-benzoxazines via Aphos–Pd(OAc)2-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides

  摘要：

  A library of 32 members of 3,4-dihydro-3-oxo-2H-1,4-benzoxazines has been synthesized from two substituted 2-aminophenols via microwave-assisted one-pot regioselective annulation of 2-bromoalkanoates and subsequent Suzuki-Miyaura cross-coupling of the chloro-substituted scaffolds. The latter transformation was carried out using our Aphos-Pd(OAc)(2) catalyst and the coupling of the aryl chlorides with arylboronic acids proceeded under mild reaction conditions at 60-80 degrees C in THF-H2O (10:1) in the presence of K3PO4 center dot 3H(2)O as the base to furnish the corresponding biaryl products in 80-98% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.057
• 作为产物：
  描述：

  2-氯苯甲醛 、 6-氨基间甲酚 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以89%的产率得到2-(2-chlorobenzylamino)-5-methylphenol
  参考文献：
  名称：

  Increasing appendage diversity on 3,4-dihydro-3-oxo-2H-1,4-benzoxazines via Aphos–Pd(OAc)2-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides

  摘要：

  A library of 32 members of 3,4-dihydro-3-oxo-2H-1,4-benzoxazines has been synthesized from two substituted 2-aminophenols via microwave-assisted one-pot regioselective annulation of 2-bromoalkanoates and subsequent Suzuki-Miyaura cross-coupling of the chloro-substituted scaffolds. The latter transformation was carried out using our Aphos-Pd(OAc)(2) catalyst and the coupling of the aryl chlorides with arylboronic acids proceeded under mild reaction conditions at 60-80 degrees C in THF-H2O (10:1) in the presence of K3PO4 center dot 3H(2)O as the base to furnish the corresponding biaryl products in 80-98% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.057