3-[3,4-Bis(benzyloxy)phenyl]-2-hydroxypropanoic Acid | 179128-86-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-[3,4-Bis(benzyloxy)phenyl]-2-hydroxypropanoic Acid
• 英文别名: 3-[3,4-bis(phenylmethoxy)phenyl]-2-hydroxypropanoic acid
• CAS: 179128-86-0
• 化学式: C₂₃H₂₂O₅
• 分子量: 378.425
• InChiKey: JLQBQSZIXGRWKY-UHFFFAOYSA-N

物化性质

• 沸点：
  579.8±45.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[3,4-Bis(benzyloxy)phenyl]-2-hydroxypropanoic Acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  Bryophyte Constituents; 7: New Synthesis of (+)-Rosmarinic Acid and Related Compounds

  摘要：

  描述了迷迭香酸（1）及其衍生物2-4的高效快捷合成方法，广泛采用了烯丙基保护基团用于羧酸和酚类构建单元。通过化学酶促拆分其苯基乳酸前体，获得了(+)-(R)-迷迭香酸。

  DOI：

  10.1055/s-1996-4289
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 126.83h， 生成 3-[3,4-Bis(benzyloxy)phenyl]-2-hydroxypropanoic Acid
  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

• Bryophyte Constituents; 7: New Synthesis of (+)-Rosmarinic Acid and Related Compounds
  作者：Theophil Eicher、Markus Ott、Andreas Speicher

  DOI：10.1055/s-1996-4289

  日期：1996.6

  Efficient and expeditious syntheses are described for rosmarinic acid (1) and its derivatives 2-4, making extensive use of allyl protective groups for both carboxylic acids and phenolic building blocks. (+)-(R)-Rosmarinic acid was obtained by a chemoenzymatic resolution of its phenyl lactic acid precursors.

  描述了迷迭香酸（1）及其衍生物2-4的高效快捷合成方法，广泛采用了烯丙基保护基团用于羧酸和酚类构建单元。通过化学酶促拆分其苯基乳酸前体，获得了(+)-(R)-迷迭香酸。
• 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.