2-methoxycarbonyl-3-(3,4-dibenzyloxyphenyl)oxirane | 203571-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methoxycarbonyl-3-(3,4-dibenzyloxyphenyl)oxirane
• 英文别名: methyl 3-(3,4-dibenzyloxyphenyl)glycidate；methyl 3-[3,4-bis(phenylmethoxy)phenyl]oxirane-2-carboxylate
• CAS: 203571-30-6
• 化学式: C₂₄H₂₂O₅
• 分子量: 390.436
• InChiKey: XMGALZTUCMCNJG-UHFFFAOYSA-N

物化性质

• 沸点：
  524.4±50.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.29
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-methoxycarbonyl-3-(3,4-dibenzyloxyphenyl)oxirane 在 palladium on activated charcoal sodium tetrahydroborate 、 三氟化硼乙醚 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 10.33h， 生成 2-[2-(Diethoxy-phosphoryl)-acetoxy]-3-(3,4-dihydroxy-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Synthese des (�)-Rosmarins�uremethylesters

  摘要：

  Regioselective cleavage of the glycidic ester 3 by BF3/ether to pyruvic acid ester 4 followed by NaBH4 reduction affords the lactic acid derivative 5a which in turn can be acylated by caffeoyl chloride 8c to yield the O-protected rosmarinic acid ester 9a. Alternatively, 9a can be prepared by acylation of 5a with diethylphosphono acetyl chloride (6c) thus generating the Wadsworth-Emmons reagent 7a which is subsequently reacted with the aldehyde 1a. The analogous reaction using the silyl protected educts 7d and 1b failed to give 9d. Finally, 9a is debenzylated by BCl3 furnishing the title compound 10a in fair total yield.

  DOI：

  10.1007/bf00806966
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 、 氯乙酸甲酯 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以90%的产率得到2-methoxycarbonyl-3-(3,4-dibenzyloxyphenyl)oxirane
  参考文献：
  名称：

  Synthese des (�)-Rosmarins�uremethylesters

  摘要：

  Regioselective cleavage of the glycidic ester 3 by BF3/ether to pyruvic acid ester 4 followed by NaBH4 reduction affords the lactic acid derivative 5a which in turn can be acylated by caffeoyl chloride 8c to yield the O-protected rosmarinic acid ester 9a. Alternatively, 9a can be prepared by acylation of 5a with diethylphosphono acetyl chloride (6c) thus generating the Wadsworth-Emmons reagent 7a which is subsequently reacted with the aldehyde 1a. The analogous reaction using the silyl protected educts 7d and 1b failed to give 9d. Finally, 9a is debenzylated by BCl3 furnishing the title compound 10a in fair total yield.

  DOI：

  10.1007/bf00806966

文献信息

• Synthese des (�)-Rosmarins�uremethylesters
  作者：E. Reimann、H. -J. Maas、T. Pflug

  DOI：10.1007/bf00806966

  日期：1997.10

  Regioselective cleavage of the glycidic ester 3 by BF3/ether to pyruvic acid ester 4 followed by NaBH4 reduction affords the lactic acid derivative 5a which in turn can be acylated by caffeoyl chloride 8c to yield the O-protected rosmarinic acid ester 9a. Alternatively, 9a can be prepared by acylation of 5a with diethylphosphono acetyl chloride (6c) thus generating the Wadsworth-Emmons reagent 7a which is subsequently reacted with the aldehyde 1a. The analogous reaction using the silyl protected educts 7d and 1b failed to give 9d. Finally, 9a is debenzylated by BCl3 furnishing the title compound 10a in fair total yield.