trans-2-benzyl-4-methyl-3-phenyl-isoxazolidin-5-one | 321851-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: trans-2-benzyl-4-methyl-3-phenyl-isoxazolidin-5-one
• 英文别名: (3S,4R)-2-benzyl-4-methyl-3-phenyl-1,2-oxazolidin-5-one
• CAS: 321851-51-8
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: GOXDUNZFDGBOKM-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-2-benzyl-4-methyl-3-phenyl-isoxazolidin-5-one 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成 3-amino-2-methyl-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of α,β-Disubstituted-β-amino Acids

  摘要：

  Highly diastereoselective and enantioselective addition of N-benzylhydroxylamine to imides 17 and 20-30 produces alpha,beta-trans-disubstituted N-benzylisoxazolidinones 19 and 31-41. These reactions proceed in 60-96% ee with 93-99% de's using 5 mol % of Mg(NTf2)2 and ligand 18. The product isoxazolidinones can be hydrogenolyzed directly to provide alpha,beta-disubstituted-beta-amino acids.

  DOI：

  10.1021/ja0372309
• 作为产物：
  描述：

  (E)-2-methyl-3-phenylacryloyl chloride 在 chiral 2,2'-cC₃H₄-bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 、 sodium hydride 、 magnesium triflimide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 trans-2-benzyl-4-methyl-3-phenyl-isoxazolidin-5-one
  参考文献：
  名称：

  Enantioselective Synthesis of α,β-Disubstituted-β-amino Acids

  摘要：

  Highly diastereoselective and enantioselective addition of N-benzylhydroxylamine to imides 17 and 20-30 produces alpha,beta-trans-disubstituted N-benzylisoxazolidinones 19 and 31-41. These reactions proceed in 60-96% ee with 93-99% de's using 5 mol % of Mg(NTf2)2 and ligand 18. The product isoxazolidinones can be hydrogenolyzed directly to provide alpha,beta-disubstituted-beta-amino acids.

  DOI：

  10.1021/ja0372309

文献信息

• BETA-AMINO ACIDS AND METHODS AND INTERMEDIATES FOR MAKING SAME
  申请人：Sibi Mukund P.

  公开号：US20110218342A1

  公开（公告）日：2011-09-08

  Disclosed are β-amino acids that are unsubstituted in the β position; that are substituted in the β position with an aryl group; that are substituted in the α position with an aryl group; that bear two substituents in the α position; and/or that are substituted in the α and β positions with groups which, together with the carbon atoms at the α and β positions, form a ring. Also disclosed are methods for making the above-mentioned β-amino acids and other β-amino acids which involve providing an α,β-unsaturated imide; converting the α,β-unsaturated imide to a 2-substituted-isoxazolidin-5-one; and converting the 2-substituted-isoxazolidin-5-one to a β-amino acid.

  披露了未在β位取代的β-氨基酸；在β位用芳基取代的β-氨基酸；在α位用芳基取代的β-氨基酸；在α位带有两个取代基的β-氨基酸；和/或在α和β位用与α和β位的碳原子一起形成环的基团取代的β-氨基酸。还披露了制备上述β-氨基酸和其他β-氨基酸的方法，包括提供α，β-不饱和亚胺；将α，β-不饱和亚胺转化为2-取代异噁唑啉-5-酮；将2-取代异噁唑啉-5-酮转化为β-氨基酸。
• US8034974B2
  申请人：——

  公开号：US8034974B2

  公开（公告）日：2011-10-11
• Enantioselective Synthesis of α,β-Disubstituted-β-amino Acids
  作者：Mukund P. Sibi、Prabagaran Narayanasamy、Sandeep G. Ghorpade、Craig P. Jasperse

  DOI：10.1021/ja0372309

  日期：2003.10.1

  Highly diastereoselective and enantioselective addition of N-benzylhydroxylamine to imides 17 and 20-30 produces alpha,beta-trans-disubstituted N-benzylisoxazolidinones 19 and 31-41. These reactions proceed in 60-96% ee with 93-99% de's using 5 mol % of Mg(NTf2)2 and ligand 18. The product isoxazolidinones can be hydrogenolyzed directly to provide alpha,beta-disubstituted-beta-amino acids.