4-(2-(4-methylbenzylideneamino)ethyl)phenol | 1085313-37-6

• 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: 4-(2-(4-methylbenzylideneamino)ethyl)phenol
• 英文别名: N-(4-methylbenzylidene)tyramine；4-[2-[(4-methylphenyl)methylideneamino]ethyl]phenol
• CAS: 1085313-37-6
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: JCINOQAUQGINQB-UHFFFAOYSA-N

物化性质

• 熔点：
  178.4-180.5 °C
• 沸点：
  405.6±38.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-(4-methylbenzylideneamino)ethyl)phenol 、 碘甲烷 在 caesium carbonate 、 盐酸 作用下， 以 甲基叔丁基醚 、 N,N-二甲基甲酰胺 、 醋酸异丙酯 、 水 、 乙酸乙酯 为溶剂， 反应 11.5h， 以85.6%的产率得到2-(4-甲氧基苯基)乙胺盐酸盐
  参考文献：
  名称：

  Syntheses of a Selective Peroxisome Proliferator Activated Receptor Modulator and Practical New Preparations of 2-(4-Alkoxyphenyl)ethylamines

  摘要：

  This article describes chemistry that was developed to give access to multigram quantities of the selective peroxisome proliferator activated receptor modulator (SPPARM), compound 1.(1) Fischer esterifications, phase transfer-catalyzed alkylations, amide couplings, crystallizations, and a new synthesis were developed to accomplish this task. In addition, an efficient method for preparing 2-(4-alkoxyphenyl)ethylamines 7a-d from tyramine 9 was developed that involves O-alkylation of intermediate Schiff base 11 and subsequent acid-catalyzed hydrolysis to afford the target molecules as crystalline hydrochloride salts.

  DOI：

  10.1021/op800215a
• 作为产物：
  描述：

  对羟基苯乙胺 、 对甲基苯甲醛 以 甲苯 为溶剂， 反应 1.55h， 以96.2%的产率得到4-(2-(4-methylbenzylideneamino)ethyl)phenol
  参考文献：
  名称：

  Syntheses of a Selective Peroxisome Proliferator Activated Receptor Modulator and Practical New Preparations of 2-(4-Alkoxyphenyl)ethylamines

  摘要：

  This article describes chemistry that was developed to give access to multigram quantities of the selective peroxisome proliferator activated receptor modulator (SPPARM), compound 1.(1) Fischer esterifications, phase transfer-catalyzed alkylations, amide couplings, crystallizations, and a new synthesis were developed to accomplish this task. In addition, an efficient method for preparing 2-(4-alkoxyphenyl)ethylamines 7a-d from tyramine 9 was developed that involves O-alkylation of intermediate Schiff base 11 and subsequent acid-catalyzed hydrolysis to afford the target molecules as crystalline hydrochloride salts.

  DOI：

  10.1021/op800215a

文献信息

• Syntheses of a Selective Peroxisome Proliferator Activated Receptor Modulator and Practical New Preparations of 2-(4-Alkoxyphenyl)ethylamines
  作者：Nicholas A. Magnus、Bret A. Astleford、John Brennan、James R. Stout、Roger W. Tharp-Taylor

  DOI：10.1021/op800215a

  日期：2009.3.20

  This article describes chemistry that was developed to give access to multigram quantities of the selective peroxisome proliferator activated receptor modulator (SPPARM), compound 1.(1) Fischer esterifications, phase transfer-catalyzed alkylations, amide couplings, crystallizations, and a new synthesis were developed to accomplish this task. In addition, an efficient method for preparing 2-(4-alkoxyphenyl)ethylamines 7a-d from tyramine 9 was developed that involves O-alkylation of intermediate Schiff base 11 and subsequent acid-catalyzed hydrolysis to afford the target molecules as crystalline hydrochloride salts.