1-((4-allyl-3-(benzyloxy)-5-(vinyloxy)phenoxy)methyl)benzene | 1133728-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-((4-allyl-3-(benzyloxy)-5-(vinyloxy)phenoxy)methyl)benzene
• 英文别名: 1-Ethenoxy-3,5-bis(phenylmethoxy)-2-prop-2-enylbenzene
• CAS: 1133728-88-7
• 化学式: C₂₅H₂₄O₃
• 分子量: 372.464
• InChiKey: BDQSXNXHOVGWOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-((4-allyl-3-(benzyloxy)-5-(vinyloxy)phenoxy)methyl)benzene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 5,7-bis(benzyloxy)-4H-chromene
  参考文献：
  名称：

  The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids

  摘要：

  The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as additive or 4-NO2PhN2BF4 as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.017
• 作为产物：
  描述：

  2-allyl-3,5-bis (benzyloxy)phenol 、 1,2-二溴乙烷 在 potassium carbonate 、 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 丙酮 、 水 、 苯 为溶剂， 反应 39.0h， 以80%的产率得到1-((4-allyl-3-(benzyloxy)-5-(vinyloxy)phenoxy)methyl)benzene
  参考文献：
  名称：

  The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids

  摘要：

  The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as additive or 4-NO2PhN2BF4 as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.017

文献信息

• The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids
  作者：Angelo H.L. Machado、Marcio A. de Sousa、Daniela C.S. Patto、Luiz F.S. Azevedo、Fernanda I. Bombonato、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2009.01.017

  日期：2009.3

  The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as additive or 4-NO2PhN2BF4 as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.