3',4'-Dimethoxy-flavan | 98200-86-3

• 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: 3',4'-Dimethoxy-flavan
• 英文别名: 3',4'-Dimethoxyflavan；2-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-chromene
• CAS: 98200-86-3
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: IDWHRFLIEWFHPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 间苯三酚 、 3',4'-Dimethoxy-flavan 生成 3-(2-Methoxyphenyl)-1-(2,4,6-trimethoxyphenyl)-1-(3,4-dimethoxyphenyl)-propan
  参考文献：
  名称：

  Weinges,K. et al., Chemische Berichte, 1963, vol. 96, p. 2870 - 2878

  摘要：

  DOI：
• 作为产物：
  描述：

  水杨醛 在 potassium carbonate 、 对甲苯磺酰肼 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 3',4'-Dimethoxy-flavan
  参考文献：
  名称：

  Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans

  摘要：

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.027

文献信息

• Transition metals catalyzed C–C and C–O bonds formation: facile synthesis of flavans and benzoxepines
  作者：B. Venkat Ramulu、L. Mahendar、J. Krishna、A. Gopi Krishna Reddy、B. Suchand、G. Satyanarayana

  DOI：10.1016/j.tet.2013.05.046

  日期：2013.9

  A simple and practical method has been developed based on intermolecular [Pd]-catalyzed C–C and an intramolecular [Cu]-catalyzed C–O bond formations for the synthesis of flavans and benzoxepines. Interestingly, the method is amenable for the synthesis of a wide variety of flavans and benzoxepines with dense functionalities on aromatic moieties. Significantly, flavans and benzoxepines are present as

  基于分子间[Pd]催化的C–C和分子内[Cu]催化的C–O键的形成，开发了一种简单而实用的方法，用于合成黄烷和苯并氧杂松。有趣的是，该方法适用于合成在芳族部分上具有致密官能团的多种黄烷和苯并二氢吡啶。值得一提的是，黄烷和苯并xepine以许多生物活性天然产物的核心/部分结构形式存在。
• 300. Autoxidation of polyphenols. Part III. Autoxidation in neutral aqueous solution of flavans related to catechin
  作者：D. E. Hathway、J. W. T. Seakins

  DOI：10.1039/jr9570001562

  日期：——
• An efficient intermolecular [Pd]-catalyzed C–C and intramolecular [Cu]-catalyzed C–O bonds formation: synthesis of functionalized flavans and benzoxepine
  作者：B. Suchand、J. Krishna、B. Venkat Ramulu、D. Dibyendu、A. Gopi Krishna Reddy、L. Mahendar、G. Satyanarayana

  DOI：10.1016/j.tetlet.2012.05.050

  日期：2012.7

  An efficient three-step strategy for the synthesis of functionalized flavans, starting from readily available 2-bromoiodobenzenes and aryl vinyl alcohols, is presented and successfully extended to benzoxepine. An intermolecular [Pd]-catalyzed C-C and an intramolecular [Cu]-catalyzed C-O bond formations have been employed as key transformations of the strategy. (C) 2012 Elsevier Ltd. All rights reserved.
• Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans
  作者：Xuyang Shang、Xiaomeng Zhou、Wei Zhang、Changfeng Wan、Junmin Chen

  DOI：10.1016/j.tet.2015.08.027

  日期：2015.10

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.
• Weinges,K. et al., Chemische Berichte, 1963, vol. 96, p. 2870 - 2878
  作者：Weinges,K. et al.

  DOI：——

  日期：——