(E)-1-(3',4'-dibenzyloxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)-1-propene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(3',4'-dibenzyloxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)-1-propene
• 英文别名: 2-[3-(3,4-bisbenzyloxy-phenyl)-allyl]-phloroglucinol；2-[(E)-3-[3,4-bis(phenylmethoxy)phenyl]prop-2-enyl]benzene-1,3,5-triol
• 化学式: C₂₉H₂₆O₅
• 分子量: 454.522
• InChiKey: JFNBTKHKVYUXFU-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 12.17h， 生成 (E)-1-(3',4'-dibenzyloxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)-1-propene
  参考文献：
  名称：

  Buffer-induced, selective mono-C-alkylation of phloroglucinol: application to the synthesis of an advanced intermediate of catechin

  摘要：

  A straightforward mono-selective and C-specific alkylation of phloroglucinol with activated alkyl halides is presented. The use of water as solvent limits the amount of over-alkylated by-products. Provided some minor changes in the experimental conditions, hydrophobic cinnamyl halides can also be reacted, thus giving a direct access to advanced intermediates of natural flavonoids. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.026

文献信息

• Phenols asC- andO-Nucleophiles in Palladium-Catalysed Allylic Substitutions
  作者：Bastien Nay、Jean-François Peyrat、Joseph Vercauteren

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2231::aid-ejoc2231>3.0.co;2-k

  日期：1999.9

  Syntheses of 2-phenyl-2H-chromene (3-flavene) and cinnamaldehyde aryloxy-hemiacetal, involving nucleophilic substitution by phenols of the π-allyl palladium complex formed from the acylal of cinnamaldehyde in the presence of catalytic amounts of palladium(0) (10 mol-%), are presented. Alternatively, the corresponding alcohol acetates furnish 1,3-diarylpropenes and cinnamyl aryl ethers. Our results

  2-苯基-2H-色烯（3-黄酮）和肉桂醛芳氧基-半缩醛的合成，包括在催化量的钯（0）存在下，由肉桂醛的酰基形成的π-烯丙基钯络合物的苯酚亲核取代（ 10 mol-%)，呈现。或者，相应的醇乙酸酯提供1,3-二芳基丙烯和肉桂基芳基醚。我们的结果证明了间苯三酚在类黄酮合成中的 Tsuji-Trost 反应中具有强大的 C-亲核性，并再次说明了苯酚的 O-亲核性。
• Buffer-induced, selective mono-C-alkylation of phloroglucinol: application to the synthesis of an advanced intermediate of catechin
  作者：Arnaud Gissot、Alain Wagner、Charles Mioskowski

  DOI：10.1016/j.tet.2004.06.026

  日期：2004.8

  A straightforward mono-selective and C-specific alkylation of phloroglucinol with activated alkyl halides is presented. The use of water as solvent limits the amount of over-alkylated by-products. Provided some minor changes in the experimental conditions, hydrophobic cinnamyl halides can also be reacted, thus giving a direct access to advanced intermediates of natural flavonoids. (C) 2004 Elsevier Ltd. All rights reserved.