(2S)-1-chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propyl stearate | 1107647-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2S)-1-chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propyl stearate
• 英文别名: [(2S)-1-chloro-3-[4-(2-methoxyethyl)phenoxy]propan-2-yl] octadecanoate
• CAS: 1107647-82-4
• 化学式: C₃₀H₅₁ClO₄
• 分子量: 511.186
• InChiKey: DITSXGHBOJEEIO-GDLZYMKVSA-N

物化性质

• 熔点：
  42-43 °C
• 沸点：
  581.3±40.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  35
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S)-1-chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propyl stearate 在 sodium hydroxide 作用下， 反应 24.0h， 以96%的产率得到(R)-3-[4-(2-甲氧基乙基)苯氧基]-1,2-环氧丙烷
  参考文献：
  名称：

  Chemoenzymatic synthesis of the potential antihypertensive agent (2R,2′S)-β-hydroxyhomometoprolol

  摘要：

  The kinetic resolution of 1-chloro-3-[4-(2-methoxyetliyl)phenoxy]-2-propanol rac-4 with Novozym 435 and vinyl stearate, a key step in the gram-scale synthesis of (2S)-2-[[(2R)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy] propyl]amino]-1-butanol (R,S)-1 a potent antihypertensive agent currently under investigation, is reported here. Our approach differs from the previously reported synthesis, which involves a tedious and poorly effective fractional crystallization of (R,S)-1. This novel approach incorporates an enzymatic resolution for the efficient preparation of the oxirane precursor (R)-3. The two main advantages arising from this strategy are the high enantioselectivity of the enzymatic process and the facilitated recovery of the hydrophobic stearate intermediate (S)-5. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.003
• 作为产物：
  描述：

  硬脂酸酯乙烯基 、 1-氯-3-[4-(2-甲氧基乙基)苯氧基]-2-丙醇 在 Novozym 435 作用下， 以 正己烷 、 丙酮 为溶剂， 反应 28.0h， 以35.4%的产率得到(2S)-1-chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propyl stearate
  参考文献：
  名称：

  Chemoenzymatic synthesis of the potential antihypertensive agent (2R,2′S)-β-hydroxyhomometoprolol

  摘要：

  The kinetic resolution of 1-chloro-3-[4-(2-methoxyetliyl)phenoxy]-2-propanol rac-4 with Novozym 435 and vinyl stearate, a key step in the gram-scale synthesis of (2S)-2-[[(2R)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy] propyl]amino]-1-butanol (R,S)-1 a potent antihypertensive agent currently under investigation, is reported here. Our approach differs from the previously reported synthesis, which involves a tedious and poorly effective fractional crystallization of (R,S)-1. This novel approach incorporates an enzymatic resolution for the efficient preparation of the oxirane precursor (R)-3. The two main advantages arising from this strategy are the high enantioselectivity of the enzymatic process and the facilitated recovery of the hydrophobic stearate intermediate (S)-5. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.003

文献信息

• Chemoenzymatic synthesis of the potential antihypertensive agent (2R,2′S)-β-hydroxyhomometoprolol
  作者：Ignacio Regla、Axel Luviano-Jardón、Patricia Demare、Enrique Hong、Alejandro Torres-Gavilán、Agustin López-Munguía、Edmundo Castillo

  DOI：10.1016/j.tetasy.2008.11.003

  日期：2008.11

  The kinetic resolution of 1-chloro-3-[4-(2-methoxyetliyl)phenoxy]-2-propanol rac-4 with Novozym 435 and vinyl stearate, a key step in the gram-scale synthesis of (2S)-2-[[(2R)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy] propyl]amino]-1-butanol (R,S)-1 a potent antihypertensive agent currently under investigation, is reported here. Our approach differs from the previously reported synthesis, which involves a tedious and poorly effective fractional crystallization of (R,S)-1. This novel approach incorporates an enzymatic resolution for the efficient preparation of the oxirane precursor (R)-3. The two main advantages arising from this strategy are the high enantioselectivity of the enzymatic process and the facilitated recovery of the hydrophobic stearate intermediate (S)-5. (C) 2008 Elsevier Ltd. All rights reserved.