8-C-β-D-glucopyranosylorobol | 66026-81-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8-C-β-D-glucopyranosylorobol
• 英文别名: 8-(β-D-glucopyranosyl)orobol；orobol-8-C-glucoside；orobol 8-C-β-glucopyranoside；3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• CAS: 66026-81-1
• 化学式: C₂₁H₂₀O₁₁
• 分子量: 448.383
• InChiKey: FONGWVNORDOJFQ-FFYOZGDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  8-C-β-D-glucopyranosylorobol 在 氢碘酸 、 苯酚 作用下， 以20 mg的产率得到3',4',5,7-四羟基异黄酮
  参考文献：
  名称：

  Heerden, Fanie R. van; Brandt, E. Vincent; Roux, David G., Journal of the Chemical Society. Perkin transactions I, 1980, p. 2463 - 2469

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-acetoxy-3,4,4',6'-tetra(benzyloxy)-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone 在 palladium dihydroxide thallium(III) nitrate 、 盐酸 、 氢气 作用下， 以 甲醇 、 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 50.0h， 以88.6 mg的产率得到8-C-β-D-glucopyranosylorobol
  参考文献：
  名称：

  Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides

  摘要：

  Genistein and orobol 8-C-beta-D-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of I and 3 and synthesized by a C-glycosylation method involving the O -> C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using TI(NO3)(3), followed by acid-catalyzed cyclization: (3) a final debenzylation by hydrogenolysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.038

文献信息

• Nunes, Domingo S.; Haag, Armin; Bestmann, Hans Juergen, Liebigs Annalen der Chemie, 1989, p. 331 - 336
  作者：Nunes, Domingo S.、Haag, Armin、Bestmann, Hans Juergen

  DOI：——

  日期：——
• Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides
  作者：Shingo Sato、Kaoru Hiroe、Toshihiro Kumazawa、Onodera Jun-ichi

  DOI：10.1016/j.carres.2006.03.038

  日期：2006.7

  Genistein and orobol 8-C-beta-D-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of I and 3 and synthesized by a C-glycosylation method involving the O -> C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using TI(NO3)(3), followed by acid-catalyzed cyclization: (3) a final debenzylation by hydrogenolysis. (c) 2006 Elsevier Ltd. All rights reserved.
• Heerden, Fanie R. van; Brandt, E. Vincent; Roux, David G., Journal of the Chemical Society. Perkin transactions I, 1980, p. 2463 - 2469
  作者：Heerden, Fanie R. van、Brandt, E. Vincent、Roux, David G.

  DOI：——

  日期：——