N,N-Diethyl-5-bromo-2-hydroxy-4-methoxy-3-(prop-2-enyl)benzamide | 165258-21-9

• 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: N,N-Diethyl-5-bromo-2-hydroxy-4-methoxy-3-(prop-2-enyl)benzamide
• 英文别名: 5-bromo-N,N-diethyl-2-hydroxy-4-methoxy-3-prop-2-enylbenzamide
• CAS: 165258-21-9
• 化学式: C₁₅H₂₀BrNO₃
• 分子量: 342.233
• InChiKey: PJSXNZCFBKAKKY-UHFFFAOYSA-N

物化性质

• 沸点：
  477.5±45.0 °C(predicted)
• 密度：
  1.312±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-Diethyl-5-bromo-2-hydroxy-4-methoxy-3-(prop-2-enyl)benzamide 在 咪唑 、 sodium tetrahydroborate 、 四甲基乙二胺 、 叔丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.74h， 生成 1,3-Dihydro-4-<(tert-butyldimethylsilyl)oxy>-6-methoxy-7-methyl-3-oxo-5-(prop-2-enyl)isobenzofuran
  参考文献：
  名称：

  The Synthesis of Mycophenolic Acid from 2,4-Dihydroxybenzoic Acid

  摘要：

  Mycophenolic acid (1) has been synthesized from 2,4-dihydroxybenzoic acid by regioselective introduction of the three required carbon substituents. A key transformation in this sequence is the introduction of the methyl substituent at position 5 by a rapid, uncatalyzed replacement of the bromide in 8 at low temperature by methyllithium. The scope and mechanism of this methylation reaction are examined.

  DOI：

  10.1021/jo00119a036
• 作为产物：
  描述：

  4-甲氧基水杨酸甲酯 在 溴 、 三甲基铝 、 potassium carbonate 、 叔丁胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 43.0h， 生成 N,N-Diethyl-5-bromo-2-hydroxy-4-methoxy-3-(prop-2-enyl)benzamide
  参考文献：
  名称：

  The Synthesis of Mycophenolic Acid from 2,4-Dihydroxybenzoic Acid

  摘要：

  Mycophenolic acid (1) has been synthesized from 2,4-dihydroxybenzoic acid by regioselective introduction of the three required carbon substituents. A key transformation in this sequence is the introduction of the methyl substituent at position 5 by a rapid, uncatalyzed replacement of the bromide in 8 at low temperature by methyllithium. The scope and mechanism of this methylation reaction are examined.

  DOI：

  10.1021/jo00119a036

文献信息

• The Synthesis of Mycophenolic Acid from 2,4-Dihydroxybenzoic Acid
  作者：John W. Patterson

  DOI：10.1021/jo00119a036

  日期：1995.7

  Mycophenolic acid (1) has been synthesized from 2,4-dihydroxybenzoic acid by regioselective introduction of the three required carbon substituents. A key transformation in this sequence is the introduction of the methyl substituent at position 5 by a rapid, uncatalyzed replacement of the bromide in 8 at low temperature by methyllithium. The scope and mechanism of this methylation reaction are examined.