N,N-Diethyl-5-bromo-2-hydroxy-6-deutero-4-methoxy-3-(prop-2-enyl)benzamide | 795288-04-9

• 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-6-deutero-4-methoxy-3-(prop-2-enyl)benzamide
• 英文别名: 3-bromo-2-deuterio-N,N-diethyl-6-hydroxy-4-methoxy-5-prop-2-enylbenzamide
• CAS: 795288-04-9
• 化学式: C₁₅H₂₀BrNO₃
• 分子量: 343.225
• InChiKey: PJSXNZCFBKAKKY-QOWOAITPSA-N

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-6-deutero-4-methoxy-3-(prop-2-enyl)benzamide 在 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.05h， 生成 2-deuterio-N,N-diethyl-4-methoxy-3-methyl-5-prop-2-enyl-6-(trideuteriomethoxy)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
• 作为产物：
  描述：

  4-甲氧基水杨酸甲酯 在 咪唑 、 氘代甲醇-d 、 四甲基乙二胺 、 四丁基氟化铵 、 溴 、 三甲基铝 、 叔丁基锂 、 potassium carbonate 、 叔丁胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 、 苯 为溶剂， 反应 44.33h， 生成 N,N-Diethyl-5-bromo-2-hydroxy-6-deutero-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.