benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate | 698386-61-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate
• 英文别名: benzyl (4S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 698386-61-7
• 化学式: C₂₀H₁₉NO₆
• 分子量: 369.374
• InChiKey: MNPQZMTVCGDTIP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate 在 三氯化硼 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.17h， 生成 3-(羟甲基)-L-酪氨酸
  参考文献：
  名称：

  A convenient two step transformation of tyrosine into the antihypertensive amino acid (S)-4-hydroxy-3-hydroxymethylphenylalanine

  摘要：

  Treatment of tyrosine with paraformaldehyde and catalytic amounts of p-toluenesulfonic acid, at reflux in toluene, directly generates benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate, which on treatment with boron trichloride in dichloromethane, affords (S)-4-hydroxy-3-hydroxymethylphenylalanine. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.02.031
• 作为产物：
  描述：

  (S)-2-(Benzyloxycarbonyl-hydroxymethyl-amino)-3-(4-hydroxy-3-hydroxymethyl-phenyl)-propionic acid 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 1.17h， 生成 benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate
  参考文献：
  名称：

  A convenient two step transformation of tyrosine into the antihypertensive amino acid (S)-4-hydroxy-3-hydroxymethylphenylalanine

  摘要：

  Treatment of tyrosine with paraformaldehyde and catalytic amounts of p-toluenesulfonic acid, at reflux in toluene, directly generates benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate, which on treatment with boron trichloride in dichloromethane, affords (S)-4-hydroxy-3-hydroxymethylphenylalanine. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.02.031

文献信息

• A convenient two step transformation of tyrosine into the antihypertensive amino acid (S)-4-hydroxy-3-hydroxymethylphenylalanine
  作者：Pietro Allevi、Riccardo Cribiù、Mario Anastasia

  DOI：10.1016/j.tetasy.2004.02.031

  日期：2004.4

  Treatment of tyrosine with paraformaldehyde and catalytic amounts of p-toluenesulfonic acid, at reflux in toluene, directly generates benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate, which on treatment with boron trichloride in dichloromethane, affords (S)-4-hydroxy-3-hydroxymethylphenylalanine. (C) 2004 Published by Elsevier Ltd.