4-(2,2-dicyanovinyl)-2-methoxyphenyl acetate | 100382-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(2,2-dicyanovinyl)-2-methoxyphenyl acetate
• 英文别名: 2-[[4-(Acetyloxy)-3-methoxyphenyl]methylene]propanedinitrile；[4-(2,2-dicyanoethenyl)-2-methoxyphenyl] acetate
• CAS: 100382-13-6
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: CLKJRHLZRWBLSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  382.3±37.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2,2-dicyanovinyl)-2-methoxyphenyl acetate 、 p-methoxyphenyl (trimethylsilyl)methyl ether 在 甲醇 、 tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以94%的产率得到4-(1,1-dicyano-3-(4-methoxyphenoxy)propan-2-yl)-2-methoxyphenyl acetate
  参考文献：
  名称：

  以α-甲硅烷基醚为烷氧基甲基自由基当量的可见光光氧化还原催化活化烯烃的氢烷氧基甲基化

  摘要：

  提出了一种新型的基于中性硅的无痕活化基团（TAG），用于可见光的光氧化还原催化的烯烃的加氢烷氧基甲基化。该反应涉及通过α-TMS-取代的醚的单电子氧化（SET）原位产生的烷氧基甲基自由基，随后将共轭物加成至活化的烯烃中。在温和的金属和不含金属的条件下都可以耐受各种官能团，从而提供了良好的优异收率。此外，将加成产物转化为有价值的合成构件，例如羧酸，γ-丁内酯和复杂的芳基烷基醚。

  DOI：

  10.1021/acs.orglett.8b02721
• 作为产物：
  描述：

  乙酰香兰素 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 4-(2,2-dicyanovinyl)-2-methoxyphenyl acetate
  参考文献：
  名称：

  以α-甲硅烷基醚为烷氧基甲基自由基当量的可见光光氧化还原催化活化烯烃的氢烷氧基甲基化

  摘要：

  提出了一种新型的基于中性硅的无痕活化基团（TAG），用于可见光的光氧化还原催化的烯烃的加氢烷氧基甲基化。该反应涉及通过α-TMS-取代的醚的单电子氧化（SET）原位产生的烷氧基甲基自由基，随后将共轭物加成至活化的烯烃中。在温和的金属和不含金属的条件下都可以耐受各种官能团，从而提供了良好的优异收率。此外，将加成产物转化为有价值的合成构件，例如羧酸，γ-丁内酯和复杂的芳基烷基醚。

  DOI：

  10.1021/acs.orglett.8b02721

文献信息

• Structural Studies on Bioactive Compounds. 32. Oxidation of Tyrphostin Protein Tyrosine Kinase Inhibitors with Hypervalent Iodine Reagents
  作者：Geoffrey Wells、Angela Seaton、Malcolm F. G. Stevens

  DOI：10.1021/jm990947f

  日期：2000.4.1

  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.
• Dihydropyrano [2,3-c] pyrazole: Novel in vitro inhibitors of yeast α-glucosidase
  作者：Hamdy Kashtoh、Munira Taj Muhammad、Jalaluddin J.A. Khan、Saima Rasheed、Ajmal Khan、Shahnaz Perveen、Kulsoom Javaid、Atia-tul-Wahab、Khalid Mohammed Khan、M. Iqbal Choudhary

  DOI：10.1016/j.bioorg.2016.01.008

  日期：2016.4

  Inhibition of alpha-glucosidase enzyme activity is a reliable approach towards controlling post-prandial hyperglycemia associated risk factors. During the current study, a series of dihydropyrano[ 2,3-c] pyrazoles (1-35) were synthesized and evaluated for their a-glucosidase inhibitory activity. Compounds 1, 4, 22, 30, and 33 were found to be the potent inhibitors of the yeast alpha-glucosidase enzyme. Mechanistic studies on most potent compounds reveled that 1, 4, and 30 were non-competitive inhibitors (K-i = 9.75 +/- 0.07, 46 +/- 0.0001, and 69.16 +/- 0.01 mu M, respectively), compound 22 is a competitive inhibitor (K-i = 190 +/- 0.016 mu M), while 33 was an uncompetitive inhibitor (K-i = 45 +/- 0.0014 mu M) of the enzyme. Finally, the cytotoxicity of potent compounds (i.e. compounds 1, 4, 22, 30, and 33) was also evaluated against mouse fibroblast 3T3 cell line assay, and no toxicity was observed. This study identifies non-cytotoxic novel inhibitors of alpha-glucosidase enzyme for further investigation as anti-diabetic agents. (C) 2016 Elsevier Inc. All rights reserved.
• Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents
  作者：Nilufa Khatun、Myeong Jun Kim、Sang Kook Woo

  DOI：10.1021/acs.orglett.8b02721

  日期：2018.10.5

  electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Various functional groups were tolerated both under mild metal and metal-free conditions to provide good to excellent yields. Furthermore, the addition products were transformed to valuable synthetic building blocks, such as carboxylic acids, γ-butyrolactones, and complex aryl alkyl ethers

  提出了一种新型的基于中性硅的无痕活化基团（TAG），用于可见光的光氧化还原催化的烯烃的加氢烷氧基甲基化。该反应涉及通过α-TMS-取代的醚的单电子氧化（SET）原位产生的烷氧基甲基自由基，随后将共轭物加成至活化的烯烃中。在温和的金属和不含金属的条件下都可以耐受各种官能团，从而提供了良好的优异收率。此外，将加成产物转化为有价值的合成构件，例如羧酸，γ-丁内酯和复杂的芳基烷基醚。
• Visible‐Light Photoredox‐Catalyzed α‐Regioselective Conjugate Addition of Allyl Groups to Activated Alkenes
  作者：Arjun Gontala、Sang Kook Woo

  DOI：10.1002/adsc.202000445

  日期：2020.8.4

  The α‐regioselective conjugate addition of allyl groups to activated alkenes is a poorly explored area of research. Herein, we report an α‐adduct and (E )‐isomer selective conjugate addition of allylsilanes to activated alkenes by visible‐light photoredox catalysis. The reaction involves allylic radicals that can be generated from allylsilanes through a photoinduced single‐electron transfer mechanism

  烯丙基在活化烯烃上的α-区域选择性共轭加成是一个研究不足的领域。在这里，我们报道了通过可见光光氧化还原催化将烯丙基硅烷与活化烯烃进行α-加合物和（E）-异构体选择性共轭加成反应。该反应涉及烯丙基自由基，该烯丙基自由基可以通过光诱导的单电子转移机理由烯丙基硅烷产生。