(2R,3S)-3,3',4',5,7-pentamethoxyflavan | 51154-08-6

• 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: (2R,3S)-3,3',4',5,7-pentamethoxyflavan
• 英文别名: 3,5,7,3',4'-pentamethyl-(+)-catechin；3,5,7,3',4'-Pentamethyl-cianidanol；(+)-catechin-pentamethylether；(2R)-2r-(3,4-Dimethoxy-phenyl)-3t,5,7-trimethoxy-chroman；((+)-Catechin)-pentamethylaether；(d-Catechin)-pentamethylaether；(2R,3S)-2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxy-3,4-dihydro-2H-chromene
• CAS: 51154-08-6
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: NNJWBZJTAKJKBL-VQTJNVASSA-N

物化性质

• 沸点：
  494.3±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3,3',4',5,7-pentamethoxyflavan 在 氢溴酸 、 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 以80%的产率得到6,8,6'-tribromo-catechin-pentamethylether
  参考文献：
  名称：

  Arnone, Alberto; Nasini, Gianluca; Panzeri, Walter, Journal of Chemical Research, Miniprint, 2003, # 11, p. 1141 - 1150

  摘要：

  DOI：
• 作为产物：
  描述：

  儿茶提取物 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 9.0h， 生成 (2R,3S)-3,3',4',5,7-pentamethoxyflavan
  参考文献：
  名称：

  Aged red wine pigments as a source of inspiration for organic synthesis—the cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores

  摘要：

  Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4 -> 8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.058

文献信息

• v. Kostanecki; Lampe, Chemische Berichte, 1906, vol. 39, p. 4017
  作者：v. Kostanecki、Lampe

  DOI：——

  日期：——
• Freudenberg; Boehme; Purrmann, Chemische Berichte, 1922, vol. 55, p. 1746
  作者：Freudenberg、Boehme、Purrmann

  DOI：——

  日期：——
• BALLENEGGER, M. E.;RIMBAULT, C. G.;ALBERT, A. I.;WEITH, A. J.;COURBAT, P.+
  作者：BALLENEGGER, M. E.、RIMBAULT, C. G.、ALBERT, A. I.、WEITH, A. J.、COURBAT, P.+

  DOI：——

  日期：——
• Kiehlmann, E.; Tracey, A. S., Canadian Journal of Chemistry, <hi>1986</hi>, vol. 64, p. 1998 - 2005
  作者：Kiehlmann, E.、Tracey, A. S.

  DOI：——

  日期：——
• Aged red wine pigments as a source of inspiration for organic synthesis—the cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores
  作者：Stefan Chassaing、Géraldine Isorez-Mahler、Marie Kueny-Stotz、Raymond Brouillard

  DOI：10.1016/j.tet.2014.10.058

  日期：2015.5

  Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4 -> 8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration. (C) 2014 Elsevier Ltd. All rights reserved.