3-O-acetyl-8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin | 69119-50-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 3-O-acetyl-8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin
• 英文别名: 8-bromo-3-O-acetyl-3',4',5,7-tetra-O-methyl-(+)-catechin；[(2R,3S)-8-bromo-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 69119-50-2；90540-13-9；105815-68-7
• 化学式: C₂₁H₂₃BrO₇
• 分子量: 467.313
• InChiKey: WCHMNHLSMJLLCN-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  <4,8>-2,3-trans-3,4-cis:2,3-trans-(-)-fisetinidol-(+)catechin heptamethyl ether diacetate 在 pyridinium hydrobromide perbromide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 为溶剂， 反应 3.17h， 生成 3-O-acetyl-8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin
  参考文献：
  名称：

  Stereospecific functionalization of the heterocyclic ring systems of flavan-3-OL and [4,8]-biflavan-3-OL derivatives with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)

  摘要：

  DOI：

  10.1016/s0040-4039(00)98614-3

文献信息

• Synthesis of condensed tannins. Part 3. Chemical shifts for determining the 6- and 8-bonding positions of ‘terminal of’(+)-catechin units
  作者：Hans K. L. Hundt、David G. Roux

  DOI：10.1039/p19810001227

  日期：——

  Pairs of 8- and 6-functionalized (Br, OH, OAc, CO2Me, and CH2Me groups) 3′,4′,5,7-tetra-O-methyl-(+)-catechins available through selective bromination and debromination reactions and hence via lithio-analogues, provide diagnostic chemical shifts of their residual 6- and 8-protons. These fall within narrow ranges [δ(CDCl3) 6.07–6.24 and 6.30–6.47 respectively] devoid of overlap, which are useful for

  通过选择性溴化可获得成对的8和6-官能化（Br，OH，OAc，CO 2 Me和CH 2 Me基）3'，4'，5,7-四-O-甲基-（+）-儿茶素脱溴反应，并因此通过硫代类似物，提供了其残留的6和8质子的诊断化学位移。它们落在狭窄的范围内[δ（CDCl 3）分别为6.07-6.24和6.30-6.47]，没有重叠，这对于区分4，6-和4，8-连接的双黄酮类化合物是有用的。还提供补充的1个H位移参数。
• Kolodziej, Herbert; Ferreira, Daneel; Roux, David G., Journal of the Chemical Society. Perkin transactions I, 1984, # 3, p. 343 - 350
  作者：Kolodziej, Herbert、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.
• STEENKAMP, J. A.;FERREIRA, D.;ROUX, D. G., TETRAHEDRON LETT., 1985, 26, N 25, 3045-3048
  作者：STEENKAMP, J. A.、FERREIRA, D.、ROUX, D. G.

  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：——