methyl 2-(5-((2R,3R,4R)-4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-3,5,7-trihydroxychroman-2-yl)benzo[d][1,3]dioxol-2-yl)acetate | 1258979-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl 2-(5-((2R,3R,4R)-4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-3,5,7-trihydroxychroman-2-yl)benzo[d][1,3]dioxol-2-yl)acetate
• 英文别名: methyl 2-[5-[(2R,3R,4R)-4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-1,3-benzodioxol-2-yl]acetate
• CAS: 1258979-22-4
• 化学式: C₂₇H₂₉NO₈
• 分子量: 495.529
• InChiKey: WVUPVBJDCHTKBI-HVZQJNOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)chroman-3,5,7-triol 、 丙炔酸甲酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 methyl 2-(5-((2R,3R,4R)-4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-3,5,7-trihydroxychroman-2-yl)benzo[d][1,3]dioxol-2-yl)acetate
  参考文献：
  名称：

  Sustainability from agricultural waste: chiral ligands from oligomeric proanthocyanidins via acid-mediated depolymerization

  摘要：

  Oligomeric proanthocyanidins (OPCs, Ar' = 3,4-(HO)(2)(C6H3) are abundant natural products found in agricultural and forestry waste such as pine bark, grape seeds, and the peels of mangosteen. We have demonstrated that the OPCs can be converted into small molecule chiral ligands by using proper nucleophiles for acid depolymerization of the OPCs. The chiral ligands may have potential for sustainable asymmetric catalysis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.123

文献信息

• [EN] METHOD OF PREPARING DERIVATIVES/OLIGOMERS OF EPICATECHIN AND APPLICATIONS THEREOF<br/>[FR] MÉTHODE DE SYNTHÈSE DE DÉRIVÉS/OLIGOMÈRES D'ÉPICATÉCHINE ET LEURS APPLICATIONS
  申请人：UNIV SINGAPORE

  公开号：WO2011073950A1

  公开（公告）日：2011-06-23

  The present invention relates to the preparation of a class of novel, optically active compounds derived from oligomeric proanthocyanidins (OPCs), more particularly to oligomers of epicatechin. These compounds include multidentate ligands and their metal complexes for use in catalysis. Methods of depolymerising proanthocyanidins to form catechins, and particularly depolymerising proanthocyanidins derived from plant sources to form novel epicatechins having application in catalysis are disclosed.

  本发明涉及一类新型的、光学活性的化合物的制备，这些化合物来源于寡聚原花青素（OPCs），更具体地说是表儿茶素寡聚体。这些化合物包括多齿配体及其金属配合物，用于催化反应。本发明还揭示了一种将原花青素降解成儿茶素的方法，特别是将植物来源的原花青素降解成新型表儿茶素，以应用于催化反应。
• METHOD OF PREPARING DERIVATIVES/OLIGOMERS OF EPICATECHIN AND APPLICATIONS THEREOF
  申请人：Huang Dejian

  公开号：US20120323016A1

  公开（公告）日：2012-12-20

  The present invention relates to the preparation of a class of novel, optically active compounds derived from oligomeric proanthocyanidins (OPCs), more particularly to oligomers of epicatechin. These compounds include multidentate ligands and their metal complexes for use in catalysis. Methods of depolymerising proanthocyanidins to form catechins, and particularly depolymerising proanthocyanidins derived from plant sources to form novel epicatechins having application in catalysis are disclosed.