methyl (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylate | 107115-19-5

• 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: methyl (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylate
• 英文别名: methyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propenoate；methyl (2E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate；methyl (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 107115-19-5
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: RCBWIWZZJPDWRU-WEVVVXLNSA-N

物化性质

• 沸点：
  398.6±42.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylate 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以69%的产率得到(E)-2-Cyano-3-[5'-((E)-2-cyano-2-methoxycarbonyl-vinyl)-6,2'-dihydroxy-5,3'-dimethoxy-biphenyl-3-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  Structural Studies on Bioactive Compounds. 32. Oxidation of Tyrphostin Protein Tyrosine Kinase Inhibitors with Hypervalent Iodine Reagents

  摘要：

  Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3 -methoxy-1-(substituted-vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted-vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-alpha, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autaphosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 mu M tamoxifen, suggesting that this compound has estrogen agonist activity.

  DOI：

  10.1021/jm990947f
• 作为产物：
  描述：

  香草醛 、 氰乙酸甲酯 在 三乙胺 作用下， 以 水 为溶剂， 以88 %的产率得到methyl (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylate
  参考文献：
  名称：

  巴西海洋真菌全细胞对 Knoevenagel 加合物的微生物转化：从水介质中去除有机化合物的绿色方法

  摘要：

  在此，我们报告了巴西海洋来源真菌的全细胞在有机化合物（特别是 Knoevenagel 加合物）的生物转化和生物降解中的应用。初步筛选...

  DOI：

  10.1080/10242422.2022.2145556

文献信息

• A convenient synthesis of pyrimidinone and pyrimidine containing bisheteroarenes and analogs
  作者：Hardesh K. Maurya、Atul Gupta

  DOI：10.1039/c4ra01689k

  日期：——

  The synthesis of pyrimidinone containing bisheteroarenes (3) and related analogs (9 and 10) by the reaction of active methylenes or substituted methyl acrylate with nitrogen containing precursors viz. amidines, or thiourea in water as well as other organic solvents was studied. Synthesized compounds have further been explored for the synthesis of diversified pyrimidines 4, 6–8, 11, 12 and 14 through

  通过活性亚甲基或取代的丙烯酸甲酯与含氮前体的反应合成含双嘧啶酮的嘧啶酮（3）和相关类似物（9和10）。water以及其他有机溶剂中的或硫脲进行了研究。合成的化合物已进一步探讨了多元化嘧啶的合成4，6-8，11，12和14通过一个顺序方法。
• Compound
  申请人：Rolic AG

  公开号：US06833421B1

  公开（公告）日：2004-12-21

  New photoactive polymers, their use as liquid crystal (LC) orientation layers and their use in the construction of unstructured and structured optical and electro-optical elements and multi-layer systems. The new photoactive polymers are crosslinkable polymers that can be readily cross linked over a relatively short irradiation time.

  新的光致活性聚合物，它们可用作液晶（LC）取向层，并可用于构建非结构化和结构化的光学和电光元件以及多层系统。这些新的光致活性聚合物是可交联的聚合物，在相对较短的辐射时间内可以很容易地交联。
• RADIOGRAPHIC ELEMENT
  申请人：EASTMAN KODAK COMPANY

  公开号：EP0555465A1

  公开（公告）日：1993-08-18
• COMPOUND
  申请人：Rolic AG

  公开号：EP1200494B1

  公开（公告）日：2004-08-18
• US5215876A
  申请人：——

  公开号：US5215876A

  公开（公告）日：1993-06-01