(4S)-3-{(2E)-3-[(tert-butoxy)phenyl]prop-2-enoyl}-4-phenyl-1,3-oxazolidin-2-one | 857083-09-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4S)-3-{(2E)-3-[(tert-butoxy)phenyl]prop-2-enoyl}-4-phenyl-1,3-oxazolidin-2-one
• CAS: 857083-09-1
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: YPVZHKTZEKRLDN-FIIODCPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S)-3-{(2E)-3-[(tert-butoxy)phenyl]prop-2-enoyl}-4-phenyl-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 、 苯硫酚铜(I) 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.1h， 生成 (2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-(tert-butoxy)phenyl]pent-4-enoic acid
  参考文献：
  名称：

  Examination of Phosphoryl-Mimicking Functionalities within a Macrocyclic Grb2 SH2 Domain-Binding Platform

  摘要：

  Reported herein are the design, synthesis, and Grb2 SH2 domain-binding affinities of several phosphoryl-mimicking groups displayed within the context of a conformationally constrained macrocyclic platform. With use of surface plasmon resonance techniques, single-digit nanomolar affinities were exhibited by phosphonic acid and malonyl-containing diacidic phosphoryl mimetics (for 4h and 4g, K-D = 1.47 and 3.62 nM, respectively). Analogues containing monoacidic phosphoryl mimetics provided affinities of K-D = 16-67 nM. Neutral phosphoryl-mimicking groups did not show appreciable binding.

  DOI：

  10.1021/jm050059m
• 作为产物：
  描述：

  1-溴-4-叔丁氧基苯 、 (S)-3-acryloyl-4-phenyloxazolidin-2-one 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 反应 12.0h， 以83%的产率得到(4S)-3-{(2E)-3-[(tert-butoxy)phenyl]prop-2-enoyl}-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Examination of Phosphoryl-Mimicking Functionalities within a Macrocyclic Grb2 SH2 Domain-Binding Platform

  摘要：

  Reported herein are the design, synthesis, and Grb2 SH2 domain-binding affinities of several phosphoryl-mimicking groups displayed within the context of a conformationally constrained macrocyclic platform. With use of surface plasmon resonance techniques, single-digit nanomolar affinities were exhibited by phosphonic acid and malonyl-containing diacidic phosphoryl mimetics (for 4h and 4g, K-D = 1.47 and 3.62 nM, respectively). Analogues containing monoacidic phosphoryl mimetics provided affinities of K-D = 16-67 nM. Neutral phosphoryl-mimicking groups did not show appreciable binding.

  DOI：

  10.1021/jm050059m