(4S)-phenylmethyl-3-N-(1,1-dimethylethoxy-carbonyl)-5(S)-ethenyl-5(S)-(2'-propenyl)oxazolidin-2-one | 160002-08-4

• 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: (4S)-phenylmethyl-3-N-(1,1-dimethylethoxy-carbonyl)-5(S)-ethenyl-5(S)-(2'-propenyl)oxazolidin-2-one
• 英文别名: tert-butyl (4S,5S)-4-benzyl-5-ethenyl-2-oxo-5-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 160002-08-4
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: NVYLWBNQCWYHEH-OXJNMPFZSA-N

物化性质

• 沸点：
  406.162±48.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.140±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-phenylmethyl-3-N-(1,1-dimethylethoxy-carbonyl)-5(S)-ethenyl-5(S)-(2'-propenyl)oxazolidin-2-one 在 sodium cyanoborohydride 、 臭氧 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 (4S,5S)-4-Benzyl-7-[(S)-1-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-2-oxo-1-oxa-3,7-diaza-spiro[4.4]nonane-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A convergent synthesis of novel conformationally restricted HIV-1 protease inhibitors

  摘要：

  Conformationally restricted HIV-1 protease inhibitors containing the transition state hydroxyl group in pyrrolidine or piperidine ring systems were synthesized stereoselectively utilizing the inherent stereochemistry of an amino acid derivative. A convergent double reductive amination strategy was used to construct the heterocyclic rings.

  DOI：

  10.1016/s0040-4039(00)77051-1
• 作为产物：
  描述：

  BOC-PHE-甲氧基甲胺 在 cerium(III) chloride 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (4S)-phenylmethyl-3-N-(1,1-dimethylethoxy-carbonyl)-5(S)-ethenyl-5(S)-(2'-propenyl)oxazolidin-2-one
  参考文献：
  名称：

  A convergent synthesis of novel conformationally restricted HIV-1 protease inhibitors

  摘要：

  Conformationally restricted HIV-1 protease inhibitors containing the transition state hydroxyl group in pyrrolidine or piperidine ring systems were synthesized stereoselectively utilizing the inherent stereochemistry of an amino acid derivative. A convergent double reductive amination strategy was used to construct the heterocyclic rings.

  DOI：

  10.1016/s0040-4039(00)77051-1

文献信息

• US5512560A
  申请人：——

  公开号：US5512560A

  公开（公告）日：1996-04-30
• A convergent synthesis of novel conformationally restricted HIV-1 protease inhibitors
  作者：B.Moon Kim、James P. Guare、Colleen M. Hanifin、Deborah J. Arford-Bickerstaff、Joseph P. Vacca、Richard G. Ball

  DOI：10.1016/s0040-4039(00)77051-1

  日期：1994.7

  Conformationally restricted HIV-1 protease inhibitors containing the transition state hydroxyl group in pyrrolidine or piperidine ring systems were synthesized stereoselectively utilizing the inherent stereochemistry of an amino acid derivative. A convergent double reductive amination strategy was used to construct the heterocyclic rings.