Benzoic acid (R)-1-(naphthalen-1-yloxymethyl)-2-(toluene-4-sulfonyloxy)-ethyl ester | 155185-35-6

• 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: Benzoic acid (R)-1-(naphthalen-1-yloxymethyl)-2-(toluene-4-sulfonyloxy)-ethyl ester
• 英文别名: [(2R)-1-(4-methylphenyl)sulfonyloxy-3-naphthalen-1-yloxypropan-2-yl] benzoate
• CAS: 155185-35-6
• 化学式: C₂₇H₂₄O₆S
• 分子量: 476.55
• InChiKey: LKVAYSFWWIPLBY-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异丙胺 、 Benzoic acid (R)-1-(naphthalen-1-yloxymethyl)-2-(toluene-4-sulfonyloxy)-ethyl ester 以 甲醇 为溶剂， 反应 4.0h， 以78%的产率得到(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-((2S,4R,4aR,6R,8aS)-2,6-diphenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-2-methanesulfonyloxy-ethyl ester 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙二醇 、 二甲基亚砜 为溶剂， 反应 207.0h， 生成 Benzoic acid (R)-1-(naphthalen-1-yloxymethyl)-2-(toluene-4-sulfonyloxy)-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.