trans-3,4-Dimethoxy-cinnamoyl- | 40918-88-5

• 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: trans-3,4-Dimethoxy-cinnamoyl-
• 英文别名: trans-3,4-Dimethoxy-cinnamoyl-(trans-3,4-dimethoxyzimtsaeureester)；[(E)-3-(3,4-dimethoxyphenyl)prop-2-enyl] (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 40918-88-5
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: GRRDUNKIGVALCZ-HFACTSAFSA-N

物化性质

• 熔点：
  80-81 °C(Solv: ethanol (64-17-5))
• 沸点：
  558.9±50.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-3,4-Dimethoxy-cinnamoyl- 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以84%的产率得到3-(3,4-dimethoxyphenyl)propyl 3-(3,4-dimethoxyphenyl)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：

  3,4-二甲氧基肉酸酸 在 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 28.25h， 生成 trans-3,4-Dimethoxy-cinnamoyl-
  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

文献信息

• Syntheses and spectral studies of some dienic and enynic esters
  作者：L.H. Klemm、K.W. Gopinath、G.C. Karaboyas、G.L. Capp、D. Hsu Lee

  DOI：10.1016/s0040-4020(01)98419-4

  日期：1964.1

  Syntheses of dienic esters of the trans-cinnamyl rans-cinnamate and trans-cinnamyl cis-cinnamate types and enynic esters of the trans-cinnamyl phenylpropiolate and phenylpropargyl trans-cinnamate types are described. Characteristic UV, IR and NMR absorption bands are noted.

  所述的二烯酯的合成反式-cinnamyl失败者肉桂酸酯和反式-cinnamyl顺-肉桂酸酯类型和的enynic酯反式-cinnamyl苯基丙和phenylpropargyl反式-肉桂酸酯类型进行说明。记录了特征性的UV，IR和NMR吸收带。
• 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.