3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin | 478241-34-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin
• 英文别名: [(2R,3R,4S)-4-acetyloxy-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 478241-34-8
• 化学式: C₄₇H₄₂O₉
• 分子量: 750.845
• InChiKey: STIQTPVHFAHBFO-WAFODNFBSA-N

物化性质

• 沸点：
  826.8±65.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  56
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin 、 (2R,3S)-5,7-二(苄氧基)-2-[3,4-二(苄氧基)苯基]-3-色满醇 在 三(五氟苯基)硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以60%的产率得到[4,8]-2,3-trans-3,4-trans:2,3-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin
  参考文献：
  名称：

  Synthesis of procyanidins by stepwise- and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-benzyl-(+)-catechin and (−)-epicatechin as a key building monomer

  摘要：

  3,4-cis-4-Acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin (1a) or (-)-epicatechin (1b) reacted high regio- and stereo-selectively with 1.5 equiv of the 5,7,3',4'-tetra-O-benzyloxyflavan-3-ol (4a or 4b) in the presence of 1 equiv of TMSOTf to give the corresponding procyanidins. On the other hand, the self-condensation of la in the presence of a catalytic amount of B(C6F5)(3) afforded wide-range procyanidins from dimer to 15-mer like a biomass. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.173
• 作为产物：
  描述：

  乙酸酐 、 (2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene-3,4-diol 在 吡啶 作用下， 以90%的产率得到3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin
  参考文献：
  名称：

  Synthesis of procyanidins by stepwise- and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-benzyl-(+)-catechin and (−)-epicatechin as a key building monomer

  摘要：

  3,4-cis-4-Acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin (1a) or (-)-epicatechin (1b) reacted high regio- and stereo-selectively with 1.5 equiv of the 5,7,3',4'-tetra-O-benzyloxyflavan-3-ol (4a or 4b) in the presence of 1 equiv of TMSOTf to give the corresponding procyanidins. On the other hand, the self-condensation of la in the presence of a catalytic amount of B(C6F5)(3) afforded wide-range procyanidins from dimer to 15-mer like a biomass. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.173