ethyl 2-[(3R)-3-hydroxy-3-[(S)-hydroxy(phenyl)methyl]-2-oxopiperidin-1-yl]acetate | 250248-77-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-[(3R)-3-hydroxy-3-[(S)-hydroxy(phenyl)methyl]-2-oxopiperidin-1-yl]acetate
• CAS: 250248-77-2
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: BUFRLOAWKRAOML-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(3R)-3-hydroxy-3-[(S)-hydroxy(phenyl)methyl]-2-oxopiperidin-1-yl]acetate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 1.0h， 生成 2-[(3R)-3-benzyl-3-hydroxy-2-oxopiperidin-1-yl]acetic acid
  参考文献：
  名称：

  Asymmetric synthesis of novel quaternary α-Hydroxy-δ-lactam dipeptide surrogates

  摘要：

  Application of the Sharpless AD protocol to a series of alpha-(E)-benzylidene-delta-lactam precursors followed by selective deoxygenation provided efficient synthetic routes to the chiral quaternary alpha-hydroxy-gamma-lactam derivatives 4 and 5. These functionalized intermediates and the diol precursors 3 are regarded as novel types of D-Phe-Pro dipeptide surrogates that are useful as enzyme active site probes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00448-5
• 作为产物：
  描述：

  ethyl 2-[(3E)-3-benzylidene-2-oxopiperidin-1-yl]acetate 在 potassium osmate(VI) 、 AD-mix-α 、 甲基磺酰胺 作用下， 以 水 、 叔丁醇 为溶剂， 以69%的产率得到ethyl 2-[(3R)-3-hydroxy-3-[(S)-hydroxy(phenyl)methyl]-2-oxopiperidin-1-yl]acetate
  参考文献：
  名称：

  Asymmetric synthesis of novel quaternary α-Hydroxy-δ-lactam dipeptide surrogates

  摘要：

  Application of the Sharpless AD protocol to a series of alpha-(E)-benzylidene-delta-lactam precursors followed by selective deoxygenation provided efficient synthetic routes to the chiral quaternary alpha-hydroxy-gamma-lactam derivatives 4 and 5. These functionalized intermediates and the diol precursors 3 are regarded as novel types of D-Phe-Pro dipeptide surrogates that are useful as enzyme active site probes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00448-5