(R)-2-hydroxy-3-(naphthalen-1-yloxy)-propyl-carbamic acid tert-butyl ester | 1173884-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-hydroxy-3-(naphthalen-1-yloxy)-propyl-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2R)-2-hydroxy-3-naphthalen-1-yloxypropyl]carbamate
• CAS: 1173884-52-0
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: MUSAKXUJZRCLKQ-CQSZACIVSA-N

物化性质

• 熔点：
  102-107 °C
• 沸点：
  515.0±40.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(1-萘氧基)-1,2-环氧丙烷 、 氨基甲酸叔丁酯 在 chiral Co(III) polymeric salen complex 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 以99.9%的产率得到
  参考文献：
  名称：

  Asymmetric Aminolytic Kinetic Resolution of Racemic Epoxides Using Recyclable Chiral Polymeric Co(III)-Salen Complexes: A Protocol for Total Utilization of Racemic Epoxide in the Synthesis of (R)-Naftopidil and (S)-Propranolol

  摘要：

  Chiral polymeric Co(III) salen complexes with chiral ((R)/(S)-BINOL, diethyl tartrate) and achiral (piper- azine and trigol) linkers with varying stereogenic centers were synthesized for the first time and used as catalysts for aminolytic kinetic resolution (AKR) of a variety of terminal epoxides and glycidyl ethers to get enantio-pure epoxides (ee, 99%) and N-protected beta-amino alcohols (ee, 99%) with quantitative yield in 16 h at RT under optimized reaction conditions. This protocol was also used for the synthesis of two enantiomerically pure drug molecules (R)-Naftopidil (alpha(1)-blocker) and (S)-Propranolol (beta-blocker) as a key step via AKR of single racemic naphthylglycidyl ether with Boc-protected isoproylamine with 100% epoxide utilization at 1 g level. The catalyst 1 was successfully recycled for a number of times.

  DOI：

  10.1021/jo4012656