methyl (Z)-(3-methyl-4-benzyloxy)-2-buten-1-oate | 449759-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (Z)-(3-methyl-4-benzyloxy)-2-buten-1-oate
• 英文别名: (2Z)-3-Methyl-4-(benzyloxy)-2-butenoic Acid Methyl Ester；methyl (Z)-3-methyl-4-phenylmethoxybut-2-enoate
• CAS: 449759-41-5
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: QHMCFYFWVUBHQT-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (Z)-(3-methyl-4-benzyloxy)-2-buten-1-oate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以85%的产率得到(2Z)-3-甲基-4-(苄氧基)-2-丁烯-1-醇
  参考文献：
  名称：

  Synthesis of 4-Diphosphocytidyl-2-C-methyl-d-erythritol and 2-C-Methyl-d-erythritol-4-phosphate

  摘要：

  2-C-Methyl-D-erythritol 4-phosphate (MEP, 2) and 4-diphosphocytidyl-2-C-methyl-D-erythritol (CDPME, 3) are metabolites in the MEP pathway for biosynthesis of isoprenoid compounds in bacteria, plant chloroplasts, and algae. The free phosphoacid of 2 was prepared from benzyloxyacetone in five steps with an overall yield of 27% and an enantiomeric ratio (er) of 75:25. Following titration to the corresponding tributylammonium salt, 2 was coupled to cytidine 5'-monophosphate using a protocol originally developed for synthesis of base-sensitive nucleoside diphosphate sugars to give 3 in 40% yield, following purification by size exclusion chromatography.

  DOI：

  10.1021/jo025736o
• 作为产物：
  描述：

  苄氧基丙酮 、 2,2,2-trifluoroethyl (methoxycarbonylmethyl)phosphonate 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 以67%的产率得到methyl (Z)-(3-methyl-4-benzyloxy)-2-buten-1-oate
  参考文献：
  名称：

  Synthesis of 4-Diphosphocytidyl-2-C-methyl-d-erythritol and 2-C-Methyl-d-erythritol-4-phosphate

  摘要：

  2-C-Methyl-D-erythritol 4-phosphate (MEP, 2) and 4-diphosphocytidyl-2-C-methyl-D-erythritol (CDPME, 3) are metabolites in the MEP pathway for biosynthesis of isoprenoid compounds in bacteria, plant chloroplasts, and algae. The free phosphoacid of 2 was prepared from benzyloxyacetone in five steps with an overall yield of 27% and an enantiomeric ratio (er) of 75:25. Following titration to the corresponding tributylammonium salt, 2 was coupled to cytidine 5'-monophosphate using a protocol originally developed for synthesis of base-sensitive nucleoside diphosphate sugars to give 3 in 40% yield, following purification by size exclusion chromatography.

  DOI：

  10.1021/jo025736o

文献信息

• Synthesis of 4-Diphosphocytidyl-2-<i>C</i>-methyl-<scp>d</scp>-erythritol and 2-<i>C</i>-Methyl-<scp>d</scp>-erythritol-4-phosphate
  作者：Andrew T. Koppisch、C. Dale Poulter

  DOI：10.1021/jo025736o

  日期：2002.7.1

  2-C-Methyl-D-erythritol 4-phosphate (MEP, 2) and 4-diphosphocytidyl-2-C-methyl-D-erythritol (CDPME, 3) are metabolites in the MEP pathway for biosynthesis of isoprenoid compounds in bacteria, plant chloroplasts, and algae. The free phosphoacid of 2 was prepared from benzyloxyacetone in five steps with an overall yield of 27% and an enantiomeric ratio (er) of 75:25. Following titration to the corresponding tributylammonium salt, 2 was coupled to cytidine 5'-monophosphate using a protocol originally developed for synthesis of base-sensitive nucleoside diphosphate sugars to give 3 in 40% yield, following purification by size exclusion chromatography.