(S)-3-hydroxy-4-(4-methoxyphenoxy)-butanoic acid | 159622-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3-hydroxy-4-(4-methoxyphenoxy)-butanoic acid
• 英文别名: (S) 3-hydroxy-4-(4-methoxyphenoxy)butanoic acid；(3S)-3-hydroxy-4-(4-methoxyphenoxy)butanoic acid
• CAS: 159622-34-1
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: QJQRGQYPJXMCLW-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (S)-3-hydroxy-4-(4-methoxyphenoxy)-butanoic acid 以 乙醚 为溶剂， 以90%的产率得到(S)-3-hydroxy-4-(4-methoxyphenoxy)-butanoic acid methyl ester
  参考文献：
  名称：

  Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics

  摘要：

  Both anantiomers of 4-p-anisyloxy-3-hydroxybutanoates 4 have been prepared in high e.e. by reduction of the corresponding beta-ketoesters or beta-ketocarboxylates with immobilized fermenting baker's yeast. the utility of these new chiral building blocks in the synthesis of pharmacologically important beta-lactam antibiotics has been demonstrated.

  DOI：

  10.1016/s0040-4020(01)89309-1
• 作为产物：
  描述：

  对甲氧基苯氧乙酸 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 38.25h， 生成 (S)-3-hydroxy-4-(4-methoxyphenoxy)-butanoic acid
  参考文献：
  名称：

  Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics

  摘要：

  Both anantiomers of 4-p-anisyloxy-3-hydroxybutanoates 4 have been prepared in high e.e. by reduction of the corresponding beta-ketoesters or beta-ketocarboxylates with immobilized fermenting baker's yeast. the utility of these new chiral building blocks in the synthesis of pharmacologically important beta-lactam antibiotics has been demonstrated.

  DOI：

  10.1016/s0040-4020(01)89309-1

文献信息

• Chemoenzymatic route to β-blockers via 3-hydroxy esters
  作者：Kerstin Wünsche、Ulrich Schwaneberg、Uwe T. Bornscheuer、Hartmut H. Meyer

  DOI：10.1016/0957-4166(96)00243-1

  日期：1996.7

  phenoxy-2-propanol) were synthesized. Key step is the lipase-catalyzed kinetic resolution of rac-3-hydroxy esters either by O-acylation using vinyl acetate or by hydrolysis of the ester group. Both approaches were highly enantioselective (> 95 %ee) with E-values > 150 using lipase from Pseudomonas cepacia. The formal synthesis of (−)-(S)-propranolol was developed in subsequent steps.

  合成了对映体纯的β-阻滞剂（普萘洛尔，阿普洛尔和1-（异丙氨基）-3-对甲氧基-苯氧基-2-丙醇）。关键步骤是使用乙酸乙烯酯的O-酰化作用或酯基的水解，可实现rac -3-羟基酯的脂肪酶催化动力学拆分。两种方法均使用洋葱假单胞菌的脂肪酶对映体选择性高（> 95％ee），E值> 150 。在随后的步骤中开发了（-）-（S）-普萘洛尔的形式合成。
• Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics
  作者：Luca Banfi、Giuseppe Cascio、Chiara Ghiron、Giuseppe Guanti、Elso Manghisi、Enrica Narisano、Renata Riva

  DOI：10.1016/s0040-4020(01)89309-1

  日期：1994.1

  Both anantiomers of 4-p-anisyloxy-3-hydroxybutanoates 4 have been prepared in high e.e. by reduction of the corresponding beta-ketoesters or beta-ketocarboxylates with immobilized fermenting baker's yeast. the utility of these new chiral building blocks in the synthesis of pharmacologically important beta-lactam antibiotics has been demonstrated.