(4S)-3-[3-(5-hydroxy-1-naphthalenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2-oxazolidinone | 861640-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S)-3-[3-(5-hydroxy-1-naphthalenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2-oxazolidinone
• CAS: 861640-60-0
• 化学式: C₂₂H₁₇NO₄
• 分子量: 359.381
• InChiKey: DBKGIIWNTTXIRC-JXOMPUQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S)-3-[3-(5-hydroxy-1-naphthalenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2-oxazolidinone 在 palladium on activated charcoal 哌啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 N-羟基-7-氮杂苯并三氮唑 、 偶氮二甲酸二异丙酯 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 三氟乙酸 、 lithium hexamethyldisilazane 、 肼 、 N,N'-二异丙基碳二亚胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 178.0h， 生成
  参考文献：
  名称：

  Synthesis of a C-terminally biotinylated macrocyclic peptide mimetic exhibiting high Grb2 SH2 domain-binding affinity

  摘要：

  Although considerable effort has been devoted to developing Grb2 SH2 domain-binding antagonists, important questions related to ligand specificity, and identification of intracellular targets remain unanswered. In order to begin addressing these issues, the design, synthesis, and evaluation of a novel biotinylated macrocycle are reported that bears biotin functionality at a C-terminal rather than the traditional N-terminal position. With a Grb2 SH2 domain-binding K-eq value of 3.4 nM, the title macrocycle (5) is among the most potent biotinylated SH2 domain-binding ligands yet disclosed. This should be a useful tool for elucidating physiological targets of certain Grb2 SH2 domain-binding antagonists. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.028
• 作为产物：
  描述：

  5-溴-1-萘酚 、 (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 14.0h， 以74%的产率得到(4S)-3-[3-(5-hydroxy-1-naphthalenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2-oxazolidinone
  参考文献：
  名称：

  Synthesis of a C-terminally biotinylated macrocyclic peptide mimetic exhibiting high Grb2 SH2 domain-binding affinity

  摘要：

  Although considerable effort has been devoted to developing Grb2 SH2 domain-binding antagonists, important questions related to ligand specificity, and identification of intracellular targets remain unanswered. In order to begin addressing these issues, the design, synthesis, and evaluation of a novel biotinylated macrocycle are reported that bears biotin functionality at a C-terminal rather than the traditional N-terminal position. With a Grb2 SH2 domain-binding K-eq value of 3.4 nM, the title macrocycle (5) is among the most potent biotinylated SH2 domain-binding ligands yet disclosed. This should be a useful tool for elucidating physiological targets of certain Grb2 SH2 domain-binding antagonists. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.028