(2S,3S,4S)-4-amino-3,4-diphenyl-2-methyl-2,3-epoxybutyric acid | 914490-00-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3S,4S)-4-amino-3,4-diphenyl-2-methyl-2,3-epoxybutyric acid
• 英文别名: (2S,3S)-3-[(S)-amino(phenyl)methyl]-2-methyl-3-phenyloxirane-2-carboxylic acid
• CAS: 914490-00-9
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: PKMKEXZCYUSPEM-UAGQMJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-amino-3,4-diphenyl-2-methyl-2,3-epoxybutyric acid 在 trimethylsilyl diazomethane 、 溶剂黄146 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 0.5h， 以98%的产率得到(3S,4S,5S)-4,5-diphenyl-3-methyl-3,4-epoxypyrrolidin-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Novel 4,5-Epoxy-1,2-oxazin-6-ones and α,β-Epoxy-γ-amino Acids from β-Lithiated Oxazolinyloxiranes and Nitrones

  摘要：

  A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5] decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-amino gamma- acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.

  DOI：

  10.1021/ol0618609
• 作为产物：
  描述：

  (1R,2S,4S')-(+)-2-(4-isopropyl-2-oxazolin-2-yl)-1-phenyl-1,2-epoxypropane 在 palladium on activated charcoal 四甲基乙二胺 、 氢气 、 仲丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 64.5h， 生成 (2S,3S,4S)-4-amino-3,4-diphenyl-2-methyl-2,3-epoxybutyric acid
  参考文献：
  名称：

  Stereoselective Synthesis of Novel 4,5-Epoxy-1,2-oxazin-6-ones and α,β-Epoxy-γ-amino Acids from β-Lithiated Oxazolinyloxiranes and Nitrones

  摘要：

  A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5] decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-amino gamma- acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.

  DOI：

  10.1021/ol0618609

文献信息

• Stereoselective Synthesis of Novel 4,5-Epoxy-1,2-oxazin-6-ones and α,β-Epoxy-γ-amino Acids from β-Lithiated Oxazolinyloxiranes and Nitrones
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi、Pasqualina Punzi

  DOI：10.1021/ol0618609

  日期：2006.10.1

  A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5] decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-amino gamma- acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.