benzyl 3-[3,4-bis(phenylmethoxy)phenyl]-2-[(E)-3-[3,4-bis(phenylmethoxy)phenyl]prop-2-enoyl]oxypropanoate | 203571-43-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: benzyl 3-[3,4-bis(phenylmethoxy)phenyl]-2-[(E)-3-[3,4-bis(phenylmethoxy)phenyl]prop-2-enoyl]oxypropanoate
• CAS: 203571-43-1
• 化学式: C₅₃H₄₆O₈
• 分子量: 810.943
• InChiKey: JBLNZGUYMGXYDX-CCFHIKDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 3-[3,4-bis(phenylmethoxy)phenyl]-2-[(E)-3-[3,4-bis(phenylmethoxy)phenyl]prop-2-enoyl]oxypropanoate 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以29%的产率得到benzyl 3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoate
  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 在 4-二甲氨基吡啶 、 sodium hydroxide 、 草酰氯 、 水 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 异丙醇 、 苯 为溶剂， 反应 6.5h， 生成 benzyl 3-[3,4-bis(phenylmethoxy)phenyl]-2-[(E)-3-[3,4-bis(phenylmethoxy)phenyl]prop-2-enoyl]oxypropanoate
  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.