5,7,4'-Trimethoxy-flavan | 4225-32-5

• 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: 5,7,4'-Trimethoxy-flavan
• 英文别名: 5,7,4'-Trimethoxyflavan；5,7-dimethoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-chromene
• CAS: 4225-32-5
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: NODOVAFZWHOGIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7,4'-Trimethoxy-flavan 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以52%的产率得到5,7,5',7'-Tetramethoxy-2,2'-bis-(4-methoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl
  参考文献：
  名称：

  (±)-Diinsininone: made nature's way

  摘要：

  We report the synthesis of diinsininone (33), the aglycone of (+/-)-diinsinin (2). Thereby, we complete the first construction of a proamhocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective beta-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.109
• 作为产物：
  描述：

  (2R)-5,7-dimethoxy-2r-(4-methoxy-phenyl)-3c-(toluene-4-sulfonyloxy)-chroman 在 盐酸 、 乙醇 、 氯仿 、 铂 、 肼 、 苯 作用下， 生成 5,7,4'-Trimethoxy-flavan
  参考文献：
  名称：

  King et al., Journal of the Chemical Society, 1955, p. 2948,2954

  摘要：

  DOI：

文献信息

• (±)-Diinsininone: made nature's way
  作者：Carolyn Selenski、Thomas R.R. Pettus

  DOI：10.1016/j.tet.2006.01.109

  日期：2006.5

  We report the synthesis of diinsininone (33), the aglycone of (+/-)-diinsinin (2). Thereby, we complete the first construction of a proamhocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective beta-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33. (c) 2006 Elsevier Ltd. All rights reserved.
• King et al., Journal of the Chemical Society, 1955, p. 2948,2954
  作者：King et al.

  DOI：——

  日期：——