3-Benzylisoferulic acid methyl ester | 316805-93-3

• 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: 3-Benzylisoferulic acid methyl ester
• 英文别名: methyl (2E)-3-[3-(benzyloxy)-4-methoxyphenyl]acrylate；methyl (E)-3-(4-methoxy-3-phenylmethoxyphenyl)prop-2-enoate
• CAS: 316805-93-3
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: XZFWKVZRKIMJFO-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  3-Benzylisoferulic acid methyl ester 在 palladium on activated charcoal 、 镍 高氯酸 、 氢气 、 四甲基胍 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 49.0h， 生成 4-(3-hydroxy-4-methoxyphenyl)-pyrrolidin-2-one
  参考文献：
  名称：

  Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs

  摘要：

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.

  DOI：

  10.1021/jm00127a009
• 作为产物：
  描述：

  甲氧羰基亚甲基三苯基正膦 、 3-苄氧基-4-甲氧基苯甲醛 以 乙腈 为溶剂， 反应 10.0h， 生成 3-Benzylisoferulic acid methyl ester
  参考文献：
  名称：

  Very Short and Efficient Syntheses of the Spermine Alkaloid Kukoamine A and Analogs Using Isolable Succinimidyl Cinnamates

  摘要：

  摘要 用多种可分离的琥珀酰亚胺基肉桂酸酯对精胺和亚精胺的初级氨基功能进行直接选择性酰化，然后进行催化氢化反应，可获得高产率的精胺生物碱 Kukoamine A 和适合结构-活性关系研究的类似物。通过芳香醛与酰化物 Ph3P=CRCO2Me 的 Wittig 反应，然后在 N,N′-二环己基碳二亚胺存在下用 N-hydroxysuccinimide 进行皂化和活化，很容易获得合适的琥珀酰亚胺肉桂酸盐。

  DOI：

  10.1246/cl.2005.264

文献信息

• A practical palladium catalyzed dehalogenation of aryl halides and α-haloketones
  作者：Jingbo Chen、Yushun Zhang、Liquan Yang、Xiang Zhang、Jianping Liu、Liang Li、Hongbin Zhang

  DOI：10.1016/j.tet.2007.03.061

  日期：2007.5

  A practical and high-yielding protocol for the dehalogenation of aromatic halides is presented. In the presence of palladium acetate, triphenylphosphine, and potassium carbonate, a number of highly functionalized aromatic halides as well as alpha-haloketones were dehalogenated with alcohols as hydrogen donors. (C) 2007 Elsevier Ltd. All rights reserved.
• Mitra; De; Karchaudhuri, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 4, p. 311 - 312
  作者：Mitra、De、Karchaudhuri

  DOI：——

  日期：——
• MARIVET, MICHEL C.;BOURGUIGNON, JEAN-JACQUES;LUGNIER, CLAIRE;MANN, ANDRE;+, J. MED. CHEM., 32,(1989) N, C. 1450-1457
  作者：MARIVET, MICHEL C.、BOURGUIGNON, JEAN-JACQUES、LUGNIER, CLAIRE、MANN, ANDRE、+

  DOI：——

  日期：——
• Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs
  作者：Michel C. Marivet、Jean Jacques Bourguignon、Claire Lugnier、Andre Mann、Jean Claude Stoclet、Camille Georges Wermuth

  DOI：10.1021/jm00127a009

  日期：1989.7

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.
• Very Short and Efficient Syntheses of the Spermine Alkaloid Kukoamine A and Analogs Using Isolable Succinimidyl Cinnamates
  作者：Thomas Garnelis、Constantinos M Athanassopoulos、Dionissios Papaioannou、Ian M Eggleston、Alan H Fairlamb

  DOI：10.1246/cl.2005.264

  日期：2005.2.1

  Direct selective acylation of the primary amino functions of spermine and spermidine with a variety of isolable succinimidyl cinnamates, followed by catalytic hydrogenation, gave high yields of the spermine alkaloid kukoamine A and analogs suitable for structure-activity relationship studies. Suitable succinimidyl cinnamates were readily obtained through Wittig reaction of aromatic aldehydes with the ylides Ph3P=CRCO2Me, followed by saponification and activation with N-hydroxysuccinimide in the presence of N,N′-dicyclohexylcarbodiimide.

  摘要 用多种可分离的琥珀酰亚胺基肉桂酸酯对精胺和亚精胺的初级氨基功能进行直接选择性酰化，然后进行催化氢化反应，可获得高产率的精胺生物碱 Kukoamine A 和适合结构-活性关系研究的类似物。通过芳香醛与酰化物 Ph3P=CRCO2Me 的 Wittig 反应，然后在 N,N′-二环己基碳二亚胺存在下用 N-hydroxysuccinimide 进行皂化和活化，很容易获得合适的琥珀酰亚胺肉桂酸盐。