epicatechin-(4β<*>8)-catechin-(4α<*>8)-epicatechin | 99297-48-0

• 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: epicatechin-(4β<*>8)-catechin-(4α<*>8)-epicatechin
• 英文别名: epicatechin-(4β[*]8)-catechin-(4α[*]8)-epicatechin；(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 99297-48-0
• 化学式: C₄₅H₃₈O₁₈
• 分子量: 866.786
• InChiKey: MOJZMWJRUKIQGL-MBADCGEUSA-N

物化性质

• 密度：
  1.747±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  63
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  331
• 氢给体数：
  15
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 epicatechin-(4β<*>8)-catechin-(4α<*>8)-epicatechin 在 吡啶 、 4-二甲氨基吡啶 作用下， 以92%的产率得到Acetic acid (2R,3R,4R,2'R,3'S,4'R,2''R,3''R)-3,5,7,5',7',3'',5'',7''-octaacetoxy-2,2',2''-tris-(3,4-diacetoxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,8';4',8'']terchromen-3'-yl ester
  参考文献：
  名称：

  Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with ­TMSOTf-Catalyzed Intermolecular Condensation

  摘要：

  本文描述了使用TMSOTf催化的缩合反应，实现七种苯甲基化原花青素三聚体的立体选择性合成。特别是，表儿茶素-(4β-8)-表儿茶素-(4β-8)-表儿茶素三聚体（原花青素C1）、儿茶素-(4α-8)-儿茶素-(4α-8)-儿茶素三聚体（原花青素C2）、表儿茶素-(4β-8)-表儿茶素-(4β-8)-儿茶素三聚体和表儿茶素-(4β-8)-儿茶素-(4α-8)-表儿茶素三聚体衍生物在大收率下获得。通过比较两种不同缩合方法合成的保护原花青素C2的1H NMR谱图，确认了苯甲基化原花青素C2的结构。最后，脱保护(+)-儿茶素和(-)-表儿茶素三聚体衍生物，获得了四种天然原花青素三聚体，收率良好。

  DOI：

  10.1055/s-2004-822905
• 作为产物：
  描述：

  [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-trans-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-(-)-epicatechin-(+)-catechin-(+)-catechin 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以87%的产率得到epicatechin-(4β<*>8)-catechin-(4α<*>8)-epicatechin
  参考文献：
  名称：

  Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with ­TMSOTf-Catalyzed Intermolecular Condensation

  摘要：

  本文描述了使用TMSOTf催化的缩合反应，实现七种苯甲基化原花青素三聚体的立体选择性合成。特别是，表儿茶素-(4β-8)-表儿茶素-(4β-8)-表儿茶素三聚体（原花青素C1）、儿茶素-(4α-8)-儿茶素-(4α-8)-儿茶素三聚体（原花青素C2）、表儿茶素-(4β-8)-表儿茶素-(4β-8)-儿茶素三聚体和表儿茶素-(4β-8)-儿茶素-(4α-8)-表儿茶素三聚体衍生物在大收率下获得。通过比较两种不同缩合方法合成的保护原花青素C2的1H NMR谱图，确认了苯甲基化原花青素C2的结构。最后，脱保护(+)-儿茶素和(-)-表儿茶素三聚体衍生物，获得了四种天然原花青素三聚体，收率良好。

  DOI：

  10.1055/s-2004-822905

文献信息

• Tannins and related compounds. XXXIII. Isolation and characterization of procyanidins in Dioscorea cirrhosa Lour.
  作者：FENGLIN HSU、GENICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.33.3293

  日期：——

  Dimeric, trimeric and tetrameric procyanidins have been isolated, together with (+)-catechin (1) and (-)-epicatechin (2), from the tubers of Dioscorea cirrhosa LOUR. (Dioscoreaceae). By comparisons of the physical and spectral data, the dimers (3-5), trimers (6-8) and tetramer (9) were identified as procyanidins obtained previously. The structures of two other trimers (10 and 11) were established by acid-catalyzed thiolytic degradation, while the formation of the tetramer (12) by condensation of the 4-carbocation of 1 with 6, in conjunction with 1H- and 13C-nuclear magnetic resonance examinations, established the structure of 12.

  从薯蓣科植物薯蓣（Dioscorea cirrhosa LOUR.）的块茎中分离出二聚体、三聚体和四聚体原花青素，以及(+)-儿茶素(1)和(-)-表儿茶素(2)。(薯蓣科）块茎中分离出来。通过物理和光谱数据的比较，二聚体（3-5）、三聚体（6-8）和四聚体（9）被确定为之前获得的原花青素。另外两种三聚体（10 和 11）的结构是通过酸催化硫解作用确定的，而四聚体（12）是通过 1 与 6 的 4-配位缩合形成的，结合 1H 和 13C 核磁共振检查，确定了 12 的结构。
• Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity
  作者：Akiko Saito、Yuki Doi、Akira Tanaka、Nobuyasu Matsuura、Makoto Ubukata、Noriyuki Nakajima

  DOI：10.1016/j.bmc.2004.07.024

  日期：2004.9

  A systematic synthesis of four natural epicatechin series procyanidin trimers 1[4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-cis-3",4"-trans: 2"",3""-trans-(-)-epi-catechin-(-)-epicatechin-(+)-catechin, [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-cis-3",4"-trans: 2"",3""-cis-tri(-)-epicatechin: procyanidin C1, [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-trans-3",4"-trans: 2"",3""-trans-(-)-epicatechin-(+)-catechin-(+)-catechin: procyanidin C4, and [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-trans-3",4"-trans: 2"",3""-cis-(-)-epicatechin-(+)-catechin-(-)-epicatechin is described. Condensation of (2R,3R,4S)-5,7,3'4'-tetra-O-benzyl-4-(2"-ethoxyethyloxy)flavan derived from (-)-epicatechin as an electrophile with the dimeric nucleophiles in the presence of TMSOTf followed by deprotection yielded trimers. Inhibitory activities on the Maillard reaction and antioxidant activity on lipid peroxide of the synthesized oligomers were also investigated. (C) 2004 Elsevier Ltd. All rights reserved.
• Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with ­TMSOTf-Catalyzed Intermolecular Condensation
  作者：Akiko Saito、Noriyuki Nakajima、Akira Tanaka、Makoto Ubukata

  DOI：10.1055/s-2004-822905

  日期：——

  A stereoselective synthesis of seven benzylated proanthocyanidin trimers with TMSOTf-catalyzed condensation reaction is described. In particular, epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (procyanidin C1), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (procyanidin C2), epicatechin-(4β-8)-epicatechin-(4β-8)-catechin trimer and epicatechin-(4β-8)-catechin-(4α-8)-epicatechin trimer derivatives were obtained in excellent yields. The structure of benzylated procyanidin C2 was confirmed by comparing the 1H NMR spectra of protected procyanidin C2 that was synthesized by two different condensation approaches. Finally, deprotection of (+)-catechin and (-)-epicatechin trimers derivatives gave four natural procyanidin trimers in good yields.

  本文描述了使用TMSOTf催化的缩合反应，实现七种苯甲基化原花青素三聚体的立体选择性合成。特别是，表儿茶素-(4β-8)-表儿茶素-(4β-8)-表儿茶素三聚体（原花青素C1）、儿茶素-(4α-8)-儿茶素-(4α-8)-儿茶素三聚体（原花青素C2）、表儿茶素-(4β-8)-表儿茶素-(4β-8)-儿茶素三聚体和表儿茶素-(4β-8)-儿茶素-(4α-8)-表儿茶素三聚体衍生物在大收率下获得。通过比较两种不同缩合方法合成的保护原花青素C2的1H NMR谱图，确认了苯甲基化原花青素C2的结构。最后，脱保护(+)-儿茶素和(-)-表儿茶素三聚体衍生物，获得了四种天然原花青素三聚体，收率良好。