Butyric acid (R)-3-bromo-4,5-dihydro-isoxazol-5-ylmethyl ester | 140384-88-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Butyric acid (R)-3-bromo-4,5-dihydro-isoxazol-5-ylmethyl ester
• 英文别名: [(5R)-3-bromo-4,5-dihydro-1,2-oxazol-5-yl]methyl butanoate
• CAS: 140384-88-9
• 化学式: C₈H₁₂BrNO₃
• 分子量: 250.092
• InChiKey: CKUSNHIFXNXECL-ZCFIWIBFSA-N

物化性质

• 沸点：
  269.6±32.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正丁酸2,2,2-三氟乙酯 、 (+/-)-3-bromo-5-hydroxymethyl isoxazoline 在 molecular sieve 作用下， 以 various solvent(s) 为溶剂， 生成 Butyric acid (R)-3-bromo-4,5-dihydro-isoxazol-5-ylmethyl ester
  参考文献：
  名称：

  介质和反应条件对脂肪酶在有机溶剂中对映选择性的影响及可能的理论依据

  摘要：

  有机溶剂的性质显着影响猪胰脂肪酶和脂肪酶PS在三氟乙基丁酸酯与两种不相关的醇（±）-磺胺醇（± ）和（±）-3-bromo- 5-羟甲基异恶唑啉（）。但是，对映选择性和溶剂的物理化学特性如疏水性和介电常数之间没有相关性。提出了基于溶剂-酶复合物形成的基本原理来解释结果。酶的对映选择性也受温度影响，但不受酰化剂链长的影响，也不受分子筛从反应介质中除去水的影响。还研究了这些参数对酯交换率的影响。

  DOI：

  10.1016/s0957-4166(00)80206-2

文献信息

• Nitrile oxides in medicinal chemistry. 4. Chemoenzymic synthesis of chiral heterocyclic derivatives
  作者：Marco De Amici、Paolo Magri、Carlo De Micheli、Francesca Cateni、Roberto Bovara、Giacomo Carrea、Sergio Riva、Gianluigi Casalone

  DOI：10.1021/jo00036a013

  日期：1992.5

  The two enantiomers of 3-bromo-5-(hydroxymethyl)-DELTA-2-isoxazoline (1) and 2-phenyl-5-(hydroxymethyl)-isoxazolidin-3-one (9) have been prepared in enantiomeric excess higher than 90% by hydrolysis of the corresponding butyrates under the catalysis of lipase PS, which was the most selective catalyst of the enzymes tested. The pairs of enantiomers of 1 and 9 were transformed into the chiral forms of the potent muscarinic ligands 3 and 5. The results obtained with the homogeneous set of esters 6, 7, 10a-d evidence a strong dependence of reaction rate and enantioselectivity of the lipase PS-catalyzed transformations upon both the size of the acyl moiety and the shape of the group carrying the alcoholic part of the ester. In the series of esters 10a-d, the best results were obtained with butyrate 10b. Quite interestingly, on passing from the butyrate of 1 to that of 9, the value of the enantiomeric ratio remained remarkably high but the enantiopreference switched from R to S. In between lies the butyrate of 2-methyl-5-(hydroxymethyl)isoxazolidin-3-one [(+/-)-6] which was barely recognized by lipase PS and yielded alcohol (R)-(-)-2 in a modest enantiomeric excess.
• Carnielli; De Amici; De Micheli, Il Farmaco, 1995, vol. 50, # 1, p. 21 - 27
  作者：Carnielli、De Amici、De Micheli、Gianferrara、Maurich、Zacchigna、Grana、Boselli

  DOI：——

  日期：——