octa-O-methyl-di-O-acetyl-bis-(+)-catechin | 3888-39-9

• 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: octa-O-methyl-di-O-acetyl-bis-(+)-catechin
• 英文别名: [(2R,3S)-8-[(2R,3S,4S)-3-acetyloxy-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-4-yl]-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 3888-39-9；7700-79-0；14617-31-3；17941-25-2；17947-27-2；28699-22-1；41093-86-1；67253-07-0；67253-08-1；97233-63-1
• 化学式: C₄₂H₄₆O₁₄
• 分子量: 774.819
• InChiKey: GZPWRAWXXKSBOE-DBMVGUGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  原花清素B3 生成 octa-O-methyl-di-O-acetyl-bis-(+)-catechin
  参考文献：
  名称：

  KOLODZIEJ, HERBERT, PHYTOCHEMISTRY, 28,(1989) N2, C. 3487-3492

  摘要：

  DOI：

文献信息

• Synthesis of condensed tannins. Part 4. A direct biomimetic approach to [4,6]- and[4,8]-biflavanoids
  作者：Jacobus J. Botha、Daneel Ferreira、David G. Roux

  DOI：10.1039/p19810001235

  日期：——

  their condensation with nucleophilic flavan-3-ols to form [4,6]- and [4,8]-biflavanoids at ambient temperatures and under mildly acidic aqueous conditions apparently simulates the initial step in condensed tannin formation in a number of natural sources. The stereospecificity (or stereoselectivity) of the reaction is conditioned mainly by the 2,3-cis or 2,3-trans stereochemistry of the parent flavan-3

  在环境温度和温和条件下，由flavan-3,4-二醇生成flavanyl-4-carbo-阳离子并与亲核flavan-3-ol缩合形成[4,6]-和[4,8]-双黄烷酮。酸性水溶液条件显然模拟了许多天然来源中单宁缩合形成的初始步骤。反应的立体特异性（或立体选择性）主要取决于母体flavan-3,4-二醇的2,3-顺式或2,3-反式立体化学，但也取决于flavan-3-ol的亲核性，和其空间专一性（或区域选择性）过程是由黄烷-3-醇的感受性A环取代取代变化引起的空间因素引起的。
• Synthesis and characterization of procyanidin dimers as their peracetates and octamethyl ether diacetates
  作者：Herbert Kolodziej

  DOI：10.1016/s0031-9422(00)81582-4

  日期：1986.4
• Steynberg, Petrus J.; Steynberg, Jan P.; Bezuidenhoudt, Barend C. B., Journal of the Chemical Society. Perkin transactions I, 1995, # 23, p. 3005 - 3012
  作者：Steynberg, Petrus J.、Steynberg, Jan P.、Bezuidenhoudt, Barend C. B.、Ferreira, Daneel

  DOI：——

  日期：——
• Delcour, Jan. A.; Ferreira, Daneel; Roux, David G., Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1711 - 1717
  作者：Delcour, Jan. A.、Ferreira, Daneel、Roux, David G.

  DOI：——

  日期：——
• Regio- and stereoselective oxidation of flavan-3-ol- 4-arylflavan-3-ol- and biflavanoid derivatives with 2,3-dichloro-56-dicyano-1,4-benzoquinone (DDQ)
  作者：Jacobus A. Steenkamp、C.Hendrik L. Mouton、Daneel Ferreira

  DOI：10.1016/s0040-4020(01)82322-x

  日期：1991.8

  The phenolic methyl ethers of flavan-3-ols, 4-beta-arylflavan-3-ols, and (-)-fisetinidol-(4-beta,8)-(+)-catechin biflavanoids are susceptible to regio- and stereoselective methoxylation at C-4 in moderate yields with DDQ in CHCl3-MeOH solution. The observed asymmetric induction with exclusive formation of 2,4-trans products is compatible with the intermediacy of a diastereogenic donor-acceptor interaction, DDQ acting as the acceptor and oxidant. The 4-funtionalized analogues are of both synthetic and degradative significance in condensed tannin chemistry.