Benzoic acid (S)-1-hydroxymethyl-2-(naphthalen-1-yloxy)-ethyl ester | 155185-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Benzoic acid (S)-1-hydroxymethyl-2-(naphthalen-1-yloxy)-ethyl ester
• 英文别名: [(2S)-1-hydroxy-3-naphthalen-1-yloxypropan-2-yl] benzoate
• CAS: 155185-34-5
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: RVYWOUAKOQLYQJ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzoic acid (S)-1-hydroxymethyl-2-(naphthalen-1-yloxy)-ethyl ester 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 为溶剂， 反应 172.0h， 生成 (S)-1-(异丙基氨基)-3-(萘基氧基)丙-2-醇
  参考文献：
  名称：

  Synthesis of enantiomerically pure (S)-(−)-propranolol from sorbitol

  摘要：

  Synthesis of enantiomerically pure (S)-(-)-propranolol, the most active optical isomer of. the widely used beta-Sympatholyticum, was achieved in high optical yield starting from sorbitol, an inexpensive and easily accessible carbohydrate. Via regioselective protection and coupling of alpha-naphthol, the key intermediate 5 was obtained. Deprotection of the intermediate acetals and successive oxidative degradation followed by some simple conversion steps lead to the formation of (S)-(-)-propranolol with high optically purity.

  DOI：

  10.1016/s0957-4166(00)82209-0
• 作为产物：
  描述：

  Benzoic acid (R)-1-formyl-2-(naphthalen-1-yloxy)-ethyl ester 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 Benzoic acid (S)-1-hydroxymethyl-2-(naphthalen-1-yloxy)-ethyl ester
  参考文献：
  名称：

  Synthesis of enantiomerically pure (S)-(−)-propranolol from sorbitol

  摘要：

  Synthesis of enantiomerically pure (S)-(-)-propranolol, the most active optical isomer of. the widely used beta-Sympatholyticum, was achieved in high optical yield starting from sorbitol, an inexpensive and easily accessible carbohydrate. Via regioselective protection and coupling of alpha-naphthol, the key intermediate 5 was obtained. Deprotection of the intermediate acetals and successive oxidative degradation followed by some simple conversion steps lead to the formation of (S)-(-)-propranolol with high optically purity.

  DOI：

  10.1016/s0957-4166(00)82209-0

文献信息

• Synthesis of enantiomerically pure (S)-(−)-propranolol from sorbitol
  作者：Ronald A. Veloo、Gerrit-Jan Koomen

  DOI：10.1016/s0957-4166(00)82209-0

  日期：1993.1

  Synthesis of enantiomerically pure (S)-(-)-propranolol, the most active optical isomer of. the widely used beta-Sympatholyticum, was achieved in high optical yield starting from sorbitol, an inexpensive and easily accessible carbohydrate. Via regioselective protection and coupling of alpha-naphthol, the key intermediate 5 was obtained. Deprotection of the intermediate acetals and successive oxidative degradation followed by some simple conversion steps lead to the formation of (S)-(-)-propranolol with high optically purity.