(2R,3S,4R)-4-(1,3,5-tri-O-methylphloroglucinol)-5,7,3',4'-tetra-O-methylflavan-3-ol | 61541-08-0

• 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,4R)-4-(1,3,5-tri-O-methylphloroglucinol)-5,7,3',4'-tetra-O-methylflavan-3-ol
• 英文别名: (2R,3S,4R)-3',4',5,7-tetramethoxy-4-(2,4,6-trimethoxyphenyl)flavan-3-ol；(2R,3S,4R)-4-(2,4,6-trimethoxyphenyl)-5,7,3',4'-tetramethoxyflavan-3-ol；(2r,3s,4r)-3',4',5,7-Tetramethoxy-4-(2,4,6-trimethoxyphenyl)-flavan-3-ol；(2R,3S,4R)-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-(2,4,6-trimethoxyphenyl)-3,4-dihydro-2H-chromen-3-ol
• CAS: 61541-08-0
• 化学式: C₂₈H₃₂O₉
• 分子量: 512.557
• InChiKey: JJOIJIJRPJGNDF-OZNIXHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-4-(1,3,5-tri-O-methylphloroglucinol)-5,7,3',4'-tetra-O-methylflavan-3-ol 、 乙酸酐 以 吡啶 为溶剂， 以80 mg的产率得到(2R,3S,4R)-2,3-trans-3,4-trans-3-acetoxy-3',4',5,7-tetramethoxy-4-(2,4,6-trimethoxyphenyl)flavan
  参考文献：
  名称：

  缩合单宁的合成。第1部分。光学纯的4-芳基黄烷-3-醇的立体选择性和立体有择合成，以及通过圆二色性评估其在C-4的绝对立体化学

  摘要：

  已知绝对构型的黄烷3,4-二醇与间苯三酚和间苯二酚在酸性介质中的C-4立体选择性和立体定向缩合反应在环境温度下进行，部分保留2,3-反式异构体的构型，并转化2 ，3-顺式类似物。所得的4-芳基黄烷-3-醇的圆二色性光谱均表现出多种棉花效应。C-4处的芳基发色团导致的高强度棉花对低波长的影响的迹象几乎总是与该手性中心的2,3-反-3,4-反，2,3-的绝对构型相关反式-3,4-顺式-和2,3-顺式-3,4-反式异构体。

  DOI：

  10.1039/p19810001213
• 作为产物：
  描述：

  (2R,4R)-4-(1,3,5-tri-O-methylphloroglucinol)-5,7,3',4'-tetra-O-methyl-flavan-3-one 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 生成 (2R,3S,4R)-4-(1,3,5-tri-O-methylphloroglucinol)-5,7,3',4'-tetra-O-methylflavan-3-ol
  参考文献：
  名称：

  Synthesis of Proanthocyanidins. Part 1. The First Oxidative Formation of the Interflavanyl Bond in Procyanidins

  摘要：

  A novel and efficient method for the oxidative condensation of tetra-O-methyl-3-oxocatech in 4 with tetra-O-methylcatechin is described. Treatment of a solution of 3 (2 equiv) and 4 (1 equiv) with silver tetrafluoroborate readily affords the phenolic per-O-methyl ethers of 3-oxocatechin(4-8)-catechin 18 and 19. Subsequent metal hydride reduction provides access to procyanidin B-3 analogues with the 3,4-cis diastereomers predominating.

  DOI：

  10.1021/ol801353u

文献信息

• Oligomeric flavanoids. Part 17. Absolute configurations of flavan-3-ols and 4-arylflavan-3-ols via the Mosher method
  作者：Wanda Rossouw、Alexander F. Hundt、Jacobus A. Steenkamp、Daneel Ferreira

  DOI：10.1016/s0040-4020(01)89554-5

  日期：1994.1

  1H NMR analysis of R-(+)- and S-(−)-α-methoxy-α-trifluoromethylphenyl acetic acid (MTPA) esters of flavan-3-ols and 4-arylflavan-3-ols permits assessment of absolute configurations of C-3 of these condensed tannin structural units.

  flavan-3-ols和4-芳基flavan-3-ols的R -（+）-和S -（-）-α-甲氧基-α-三氟甲基苯基乙酸（MTPA）酯的1 H NMR分析这些缩合的单宁结构单元的C-3中
• Porter, Lawrence J.; Wong, Rosalind Y.; Benson, Mabry, Journal of Chemical Research, Miniprint, 1986, # 3, p. 830 - 880
  作者：Porter, Lawrence J.、Wong, Rosalind Y.、Benson, Mabry、Chan, Bock G.

  DOI：——

  日期：——
• Synthesis of Proanthocyanidins. Part 1. The First Oxidative Formation of the Interflavanyl Bond in Procyanidins
  作者：Matthew C. Achilonu、Susan L. Bonnet、Jan H. van der Westhuizen

  DOI：10.1021/ol801353u

  日期：2008.9.1

  A novel and efficient method for the oxidative condensation of tetra-O-methyl-3-oxocatech in 4 with tetra-O-methylcatechin is described. Treatment of a solution of 3 (2 equiv) and 4 (1 equiv) with silver tetrafluoroborate readily affords the phenolic per-O-methyl ethers of 3-oxocatechin(4-8)-catechin 18 and 19. Subsequent metal hydride reduction provides access to procyanidin B-3 analogues with the 3,4-cis diastereomers predominating.
• Synthesis of condensed tannins. Part 1. Stereoselective and stereospecific syntheses of optically pure 4-arylflavan-3-ols, and assessment of their absolute stereochemistry at C-4 by means of circular dichroism
  作者：Jacobus J. Botha、Desmond A. Young、Daneel Ferreira、David G. Roux

  DOI：10.1039/p19810001213

  日期：——

  Stereoselective and also stereospecific condensation at C-4 of flavan-3,4-diols of known absolute configuration with phloroglucinol and resorcinol in acid medium proceeds at ambient temperatures with partial retention of configuration for 2,3-trans-isomers and with inversion for 2,3-cis-analogues. Circular dichroism spectra of the resultant 4-arylflavan-3-ols all exhibit multiple Cotton effects. The

  已知绝对构型的黄烷3,4-二醇与间苯三酚和间苯二酚在酸性介质中的C-4立体选择性和立体定向缩合反应在环境温度下进行，部分保留2,3-反式异构体的构型，并转化2 ，3-顺式类似物。所得的4-芳基黄烷-3-醇的圆二色性光谱均表现出多种棉花效应。C-4处的芳基发色团导致的高强度棉花对低波长的影响的迹象几乎总是与该手性中心的2,3-反-3,4-反，2,3-的绝对构型相关反式-3,4-顺式-和2,3-顺式-3,4-反式异构体。