(E)-((E)-3-(4-methoxyphenyl)allyl) 3-(4-methoxyphenyl)acrylate | 850176-66-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-((E)-3-(4-methoxyphenyl)allyl) 3-(4-methoxyphenyl)acrylate
• 英文别名: 3-(4-methoxyphenyl)propenyl 3-(4-methoxyphenyl)allylate；[(E)-3-(4-methoxyphenyl)prop-2-enyl] (E)-3-(4-methoxyphenyl)prop-2-enoate
• CAS: 850176-66-8
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: HUPVFCIVNRUXGA-LDKZCNOQSA-N

物化性质

• 熔点：
  63-64 °C(Solv: hexane (110-54-3))
• 沸点：
  500.3±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-((E)-3-(4-methoxyphenyl)allyl) 3-(4-methoxyphenyl)acrylate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3-(4'-methoxyphenyl)propyl-3-(4'-methoxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441
• 作为产物：
  描述：

  (2E)-3-(4-甲氧基苯基)-2-丙烯-1-醇 在 2,2,6,6-四甲基哌啶氧化物 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 4.0h， 以83%的产率得到(E)-((E)-3-(4-methoxyphenyl)allyl) 3-(4-methoxyphenyl)acrylate
  参考文献：
  名称：

  N-杂环卡宾催化醛与醇/硫醇的氧化偶联和烯丙醇的一锅氧化/酯化

  摘要：

  描述了一种涉及 N-杂环卡宾催化剂和 2,2,6,6-四甲基哌啶 N-氧基 (TEMPO) 的多功能卡宾催化氧化方案，用于合成酯、肉桂酸和硫酯。通过醛与脂肪醇、烯丙醇和芳香醇、苄基硫醇和水的无金属偶联，可以获得多种酯、硫酯和肉桂酸。除了醛与亲核试剂的氧化偶联外，在我们的氧化偶联条件下还发现了饱和醛的脱氢和烯丙醇的氧化。与其他 TEMPO 介导的氧化酯化反应不同，该反应不会通过 TEMPO 酯中间体进行以形成酯和硫酯。

  DOI：

  10.1002/ejoc.201301337

文献信息

• Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues
  作者：Li Hong Hu、Hong Bin Zou、Jing Xu Gong、Hai Bo Li、Lei Xiang Yang、Wei Cheng、Chang Xin Zhou、Hua Bai、Françoise Guéritte、Yu Zhao

  DOI：10.1021/np0496441

  日期：2005.3.1

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.
• N-Heterocyclic Carbene Catalysed Oxidative Coupling of Aldehydes with Alcohols/Thiols and One-Pot Oxidation/Esterification of Allylic Alcohols
  作者：Miran Ji、Xi Wang、Yu Na Lim、Ye-Won Kang、Hye-Young Jang

  DOI：10.1002/ejoc.201301337

  日期：2013.12

  carbene-catalysed oxidation protocol involving N-heterocyclic carbene catalysts and 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) is described for the synthesis of esters, cinnamic acids, and thioesters. A wide range of esters, thioesters, and cinnamic acids were obtained by metal-free coupling of aldehydes with aliphatic, allylic and aromatic alcohols, benzyl mercaptan, and water. In addition to the oxidative coupling

  描述了一种涉及 N-杂环卡宾催化剂和 2,2,6,6-四甲基哌啶 N-氧基 (TEMPO) 的多功能卡宾催化氧化方案，用于合成酯、肉桂酸和硫酯。通过醛与脂肪醇、烯丙醇和芳香醇、苄基硫醇和水的无金属偶联，可以获得多种酯、硫酯和肉桂酸。除了醛与亲核试剂的氧化偶联外，在我们的氧化偶联条件下还发现了饱和醛的脱氢和烯丙醇的氧化。与其他 TEMPO 介导的氧化酯化反应不同，该反应不会通过 TEMPO 酯中间体进行以形成酯和硫酯。