(S)-4-benzyl-3-(2-benzyl-prop-2-enoyl)-1,3-oxazolidin-2-one | 439799-67-4

• 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: (S)-4-benzyl-3-(2-benzyl-prop-2-enoyl)-1,3-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-(2-benzylprop-2-enoyl)-1,3-oxazolidin-2-one
• CAS: 439799-67-4
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: VCAMCEAGTLNSLG-SFHVURJKSA-N

物化性质

• 沸点：
  464.7±48.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-(2-benzyl-prop-2-enoyl)-1,3-oxazolidin-2-one 在 lithium hydroxide 、 水 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (S)-3-[(1-Acetylamino-2-phenyl-ethyl)-hydroxy-phosphinoyl]-2-benzyl-propionic acid
  参考文献：
  名称：

  Enantioselective synthesis of phosphinyl peptidomimetics via an asymmetric Michael reaction of phosphinic acids with acrylate derivatives

  摘要：

  Asymmetric Michael reaction of phosphinic or aminophosphinic acids with acrylate derivatives afforded phosphinyl dipepti-domimetics in excellent yields ( > 90%). Chiral induction of substituents at the alpha-position of acrylate derivatives of Evans oxazolidinone type auxiliaries was obtained in moderate to excellent diastercomeric and enantiorneric excesses (50-98%). Pure diastereomers and enantiomers of phosphinyl dipeptidomimetics 16-19 were also successfully separated by HPLC. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01388-2
• 作为产物：
  描述：

  苄基丙二酸 在 N-甲基吗啉 、 正丁基锂 、 二乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.0h， 生成 (S)-4-benzyl-3-(2-benzyl-prop-2-enoyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Enantioselective synthesis of phosphinyl peptidomimetics via an asymmetric Michael reaction of phosphinic acids with acrylate derivatives

  摘要：

  Asymmetric Michael reaction of phosphinic or aminophosphinic acids with acrylate derivatives afforded phosphinyl dipepti-domimetics in excellent yields ( > 90%). Chiral induction of substituents at the alpha-position of acrylate derivatives of Evans oxazolidinone type auxiliaries was obtained in moderate to excellent diastercomeric and enantiorneric excesses (50-98%). Pure diastereomers and enantiomers of phosphinyl dipeptidomimetics 16-19 were also successfully separated by HPLC. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01388-2

文献信息

• Peptide deformylase inhibitors of Mycobacterium tuberculosis: Synthesis, structural investigations, and biological results
  作者：Arkadius Pichota、Jeyaraj Duraiswamy、Zheng Yin、Thomas H. Keller、Jenefer Alam、Sarah Liung、Gladys Lee、Mei Ding、Gang Wang、Wai Ling Chan、Mark Schreiber、Ida Ma、David Beer、Xinyi Ngew、Kakoli Mukherjee、Mahesh Nanjundappa、Jeanette W.P. Teo、Pamela Thayalan、Amelia Yap、Thomas Dick、Wuyi Meng、Mei Xu、James Koehn、Shi-Hao Pan、Kirk Clark、Xiaoling Xie、Carolyn Shoen、Michael Cynamon

  DOI：10.1016/j.bmcl.2008.10.040

  日期：2008.12

  Bacterial peptide deformylase (PDF) belongs to a subfamily of metalloproteases catalyzing the removal of the N-terminal formyl group from newly synthesized proteins. We report the synthesis and biological activity of highly potent inhibitors of Mycobacterium tuberculosis (Mtb) PDF enzyme as well as the first X-ray crystal structure of Mtb PDF. Structure-activity relationship and crystallographic data clarified the structural requirements for high enzyme potency and cell based potency. Activities against single and multi-drug-resistant Mtb strains are also reported.
• The Rational Design of Drugs with Phos-phonic/phinic Acids as Enzyme Inhibitors Isosteric Receptor Ligands
  作者：Frank H. Ebetino、David L. Soper、Michelle J. Dirr、Mark W. Lundy、Glen Mieling、John A. Wos、Mitchell A. deLong、Xuewei Liu

  DOI：10.1080/10426500212317

  日期：2002.6.1
• Enantioselective synthesis of phosphinyl peptidomimetics via an asymmetric Michael reaction of phosphinic acids with acrylate derivatives
  作者：Xuewei Liu、X.Eric Hu、Xinrong Tian、Adam Mazur、Frank H Ebetino

  DOI：10.1016/s0022-328x(01)01388-2

  日期：2002.3

  Asymmetric Michael reaction of phosphinic or aminophosphinic acids with acrylate derivatives afforded phosphinyl dipepti-domimetics in excellent yields ( > 90%). Chiral induction of substituents at the alpha-position of acrylate derivatives of Evans oxazolidinone type auxiliaries was obtained in moderate to excellent diastercomeric and enantiorneric excesses (50-98%). Pure diastereomers and enantiomers of phosphinyl dipeptidomimetics 16-19 were also successfully separated by HPLC. (C) 2002 Elsevier Science B.V. All rights reserved.