methyl (3S)-3-(m-chlorobenzoyloxy)-N-trifluoroacetylalaninate | 161771-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (3S)-3-(m-chlorobenzoyloxy)-N-trifluoroacetylalaninate
• 英文别名: [(2S)-3-methoxy-3-oxo-2-[(2,2,2-trifluoroacetyl)amino]propyl] 3-chlorobenzoate
• CAS: 161771-71-7
• 化学式: C₁₃H₁₁ClF₃NO₅
• 分子量: 353.682
• InChiKey: LXRGBXOMHUQPQG-VIFPVBQESA-N

物化性质

• 沸点：
  455.2±45.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (3S)-3-(m-chlorobenzoyloxy)-N-trifluoroacetylalaninate 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以32%的产率得到L-丝氨酸盐酸盐
  参考文献：
  名称：

  Stereospecific synthesis of α-deuteriated α-amino acids: regiospecific deuteriation of chiral 3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazines

  摘要：

  Base-catalysed deuteriation of (3R)- or (3S)-3-isopropyl-2.5-dimethoxy-3,6-dihydropyrazines in refluxing (CH3OH)-H-2-(H2O)-H-2 gives the [6-H-2(2)]-isotopomer in excellent yields without disturbing the stereogenic centre at C-3. These compounds provide convenient and efficient access to a range of (R)- and (S)-alpha-deuteriated alpha-amino acids, including serine, aspartic acid, allylglycine and phenylalanine, via alkylation of the butyllithium generated C-6 anion.

  DOI：

  10.1039/p19950000157
• 作为产物：
  描述：

  (3S)-3-methoxycarbonyl-3-trifluoroacetylaminopropanoyl chloride 以 吡啶 、 四氯化碳 、 乙醚 为溶剂， 反应 148.0h， 生成 methyl (3S)-3-(m-chlorobenzoyloxy)-N-trifluoroacetylalaninate
  参考文献：
  名称：

  Stereospecific synthesis of α-deuteriated α-amino acids: regiospecific deuteriation of chiral 3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazines

  摘要：

  Base-catalysed deuteriation of (3R)- or (3S)-3-isopropyl-2.5-dimethoxy-3,6-dihydropyrazines in refluxing (CH3OH)-H-2-(H2O)-H-2 gives the [6-H-2(2)]-isotopomer in excellent yields without disturbing the stereogenic centre at C-3. These compounds provide convenient and efficient access to a range of (R)- and (S)-alpha-deuteriated alpha-amino acids, including serine, aspartic acid, allylglycine and phenylalanine, via alkylation of the butyllithium generated C-6 anion.

  DOI：

  10.1039/p19950000157

文献信息

• Stereospecific synthesis of α-deuteriated α-amino acids: regiospecific deuteriation of chiral 3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazines
  作者：Janet E. Rose、Paul D. Leeson、David Gani

  DOI：10.1039/p19950000157

  日期：——

  Base-catalysed deuteriation of (3R)- or (3S)-3-isopropyl-2.5-dimethoxy-3,6-dihydropyrazines in refluxing (CH3OH)-H-2-(H2O)-H-2 gives the [6-H-2(2)]-isotopomer in excellent yields without disturbing the stereogenic centre at C-3. These compounds provide convenient and efficient access to a range of (R)- and (S)-alpha-deuteriated alpha-amino acids, including serine, aspartic acid, allylglycine and phenylalanine, via alkylation of the butyllithium generated C-6 anion.