tert-butyl N-[(2S)-1-hydroxy-3-[(3R)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamate | 249736-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl N-[(2S)-1-hydroxy-3-[(3R)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamate
• CAS: 249736-44-5
• 化学式: C₁₂H₂₂N₂O₄
• 分子量: 258.318
• InChiKey: IASISKBRBNTMFU-BDAKNGLRSA-N

物化性质

• 沸点：
  480.0±20.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-hydroxy-3-[(3R)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 以64%的产率得到(S)-2-((tert-Butoxycarbonyl)amino)-3-((R)-2-oxopyrrolidin-3-yl)propanoic acid
  参考文献：
  名称：

  Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase

  摘要：

  A series of keto-glutamine tetrapeptide analogs containing a 2-oxo-pyrrolidine ring as a glutamine side chain mimic were synthesized with both R and S configuration at the beta-carbon. Compounds bearing a phthalhydrazide moiety show improved reversible inhibition of HAV 3C proteinase in the low micromolar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.021
• 作为产物：
  描述：

  (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-cyanomethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 platinum(IV) oxide lithium hydroxide 、 氯仿 、 四丁基氟化铵 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 78.0h， 生成 tert-butyl N-[(2S)-1-hydroxy-3-[(3R)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamate
  参考文献：
  名称：

  Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase

  摘要：

  A series of keto-glutamine tetrapeptide analogs containing a 2-oxo-pyrrolidine ring as a glutamine side chain mimic were synthesized with both R and S configuration at the beta-carbon. Compounds bearing a phthalhydrazide moiety show improved reversible inhibition of HAV 3C proteinase in the low micromolar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.021

文献信息

• Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase
  作者：Rajendra P Jain、John C Vederas

  DOI：10.1016/j.bmcl.2004.05.021

  日期：2004.7

  A series of keto-glutamine tetrapeptide analogs containing a 2-oxo-pyrrolidine ring as a glutamine side chain mimic were synthesized with both R and S configuration at the beta-carbon. Compounds bearing a phthalhydrazide moiety show improved reversible inhibition of HAV 3C proteinase in the low micromolar range. (C) 2004 Elsevier Ltd. All rights reserved.