(E)-6-oxo-6-[(4S)-(2-oxo-4-phenyl-oxazolidin-3-yl)]hex-4-enoic acid tert-butyl ester | 600708-96-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-6-oxo-6-[(4S)-(2-oxo-4-phenyl-oxazolidin-3-yl)]hex-4-enoic acid tert-butyl ester
• 英文别名: tert-butyl (E)-6-oxo-6-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]hex-4-enoate
• CAS: 600708-96-1
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: DNAWHEXYEAUSBG-USYSOWRXSA-N

物化性质

• 熔点：
  93.0-94.0 °C
• 沸点：
  437.8±55.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-6-oxo-6-[(4S)-(2-oxo-4-phenyl-oxazolidin-3-yl)]hex-4-enoic acid tert-butyl ester 在 palladium on activated charcoal 三乙基硅烷 、 lithium hydroxide 、 sodium azide 、 草酰氯 、 copper(I) bromide dimethylsulfide complex 、 氢气 、 双氧水 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二硫化碳 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 28.66h， 生成 (1R,9R,12S)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-12-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of a New Conformation-Constrained l-Tyrosine Analogue as a Potential Scaffold for SH2 Domain Ligands

  摘要：

  The enantioselective synthesis of a new tricyclic tyrosine analogue is reported. This conformation-contrained SH2 domain ligand scaffold 2 was designed on the basis of the natural ligand, whose structure contains the elements of a tyrosine moiety having chi(1) and chi(2) angles constrained to values observed for a phosp(h)otyrosyl (pTyr) residue bound to the p56(lck) SH2 domain. It represents a unique, highly constrained amino acid, which may be of value in signal transduction studies. Three key steps, an asymmetric tandem Michael addition, an intramolecular Friedel-Crafts reaction, and an intramolecular Mannich reaction, were successfully applied in the presented synthetic route.

  DOI：

  10.1021/jo0340152
• 作为产物：
  描述：

  4-羟基丁酸叔丁酯 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.25h， 生成 (E)-6-oxo-6-[(4S)-(2-oxo-4-phenyl-oxazolidin-3-yl)]hex-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of a New Conformation-Constrained l-Tyrosine Analogue as a Potential Scaffold for SH2 Domain Ligands

  摘要：

  The enantioselective synthesis of a new tricyclic tyrosine analogue is reported. This conformation-contrained SH2 domain ligand scaffold 2 was designed on the basis of the natural ligand, whose structure contains the elements of a tyrosine moiety having chi(1) and chi(2) angles constrained to values observed for a phosp(h)otyrosyl (pTyr) residue bound to the p56(lck) SH2 domain. It represents a unique, highly constrained amino acid, which may be of value in signal transduction studies. Three key steps, an asymmetric tandem Michael addition, an intramolecular Friedel-Crafts reaction, and an intramolecular Mannich reaction, were successfully applied in the presented synthetic route.

  DOI：

  10.1021/jo0340152

文献信息

• Synthesis of a New Conformation-Constrained <scp>l</scp>-Tyrosine Analogue as a Potential Scaffold for SH2 Domain Ligands
  作者：Fa Liu、Hui-Yan Zha、Zhu-Jun Yao

  DOI：10.1021/jo0340152

  日期：2003.8.1

  The enantioselective synthesis of a new tricyclic tyrosine analogue is reported. This conformation-contrained SH2 domain ligand scaffold 2 was designed on the basis of the natural ligand, whose structure contains the elements of a tyrosine moiety having chi(1) and chi(2) angles constrained to values observed for a phosp(h)otyrosyl (pTyr) residue bound to the p56(lck) SH2 domain. It represents a unique, highly constrained amino acid, which may be of value in signal transduction studies. Three key steps, an asymmetric tandem Michael addition, an intramolecular Friedel-Crafts reaction, and an intramolecular Mannich reaction, were successfully applied in the presented synthetic route.