4-(4'-cyanobenzylidene)-2-phenyloxazolin-5-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(4'-cyanobenzylidene)-2-phenyloxazolin-5-one
• 英文别名: (Z)-4-(4-cyanobenzylidene)-2-phenyl-5(4H)-oxazolone；(Z)-4-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)benzonitrile；4-[(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]benzonitrile
• 化学式: C₁₇H₁₀N₂O₂
• 分子量: 274.279
• InChiKey: TVAGPAAYXQKMPE-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4'-cyanobenzylidene)-2-phenyloxazolin-5-one 生成 N-[(E)-3-(tert-butylamino)-1-(4-cyanophenyl)-3-oxoprop-1-en-2-yl]benzamide
  参考文献：
  名称：

  KUHN, DAVID GEORGE

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 在 盐酸 、 乙酸酐 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 4-(4'-cyanobenzylidene)-2-phenyloxazolin-5-one
  参考文献：
  名称：

  Design, synthesis and evaluation of novel phenyl propionamide derivatives as non-nucleoside hepatitis B virus inhibitors

  摘要：

  As an ongoing search for potent non-nucleoside anti-HBV agents with novel structures, we described a series of phenyl propionamide derivatives (3a-b, 4a-e, 7a-g, 8a-h and 9a-b) by pharmacophore fusion strategy in the present work. All the compounds exhibited an anti-HBV activity to some extent. Among them, compounds 8d and 9b displayed most potent anti-HBV activity with IC50 values on HBV DNA replication of 0.46 and 0.14 mu M, respectively. And the selective index values of 8d and 9b were more than 217.39 and 153.14, suggesting that 8d and 9b exhibited favorable safety profiles. Interestingly, 8d and 9b possessed significantly antiviral activities against lamivudine and entecavir resistant HBV mutants with IC50 values of 0.77 and 0.32 mu M. Notably, preliminary anti-HBV action mechanism studies showed that 8d could inhibit intracellular HBV pgRNA and RT activity of the HBV polymerase. Molecular docking studies suggested that compound 8d could fit into the dimer-dimer interface of HBV core protein by hydrophobic interaction. In addition, in silico prediction of physicochemical properties showed that 8d conformed well to the Lipinski's rule of five, suggesting its potential for use as a drug like molecule. Taken together, 8d possessed significantly anti-HBV activity, low toxicity, diverse anti-HBV mechanism and favorable physicochemical properties, and warranted further investigation as a promising non-nucleoside anti-HBV candidate. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.042

文献信息

• Diastereoselective synthesis of 5-iminooxazolines and their subsequent transformation to α,α-disubstituted dipeptide esters: a formal [4+1] cycloaddition reaction of cyclohexyl isocyanide and Z-alkyl-α-benzoyl amino-acrylates
  作者：Abbas Ali Esmaeili、Shima Shahmansouri、Azizollah Habibi、Ali Reza Fakhari

  DOI：10.1016/j.tet.2012.06.073

  日期：2012.9

  A novel atom economical diastereoselective synthesis of 5-iminooxazolines and their subsequent transformation to α,α-disubstituted dipeptide esters is described. Heating a mixture of cyclohexyl isocyanide and Z-α-benzoyl amino-acrylic acid alkyl esters under solvent-free conditions, afforded 5-iminooxazolines, which, upon specifications provided α,α-disubstituted dipeptide esters in good yield.

  描述了5-亚氨基恶唑啉的新颖的原子经济的非对映选择性合成及其随后转化为α，α-二取代的二肽酯。在无溶剂条件下加热环己基异氰化物和Z -α-苯甲酰基氨基丙烯酸烷基酯的混合物，得到5-亚氨基恶唑啉，根据规格，该α-α-二取代的二肽酯产率高。
• Metal-free and benign approach for the synthesis of dihydro-5′<i>H</i>-spiro[benzo[<i>c</i>]chromene-8,4′-oxazole]-5′,6(7<i>H</i>)-dione scaffolds as masked amino acids
  作者：Behnaz Shafiee、Joseph Duffield、Rudy Timm、Rohana Liyanage、Jackson O. Lay、Ahmad R. Khosropour、Hadi Amiri Rudbari、M. Hassan Beyzavi

  DOI：10.1039/c9gc00428a

  日期：——

  straightforward, and three-component condensation/cascade reaction of 4-hydroxycoumarins and (Z)-azlactones to construct diversified dihydro-5′H-spiro[benzo[c]chromene-8,4′-oxazole]-5′,6(7H)-diones as new masked amino acid derivatives has been developed with high to excellent yields and regio- and diastereoselectivity. This metal-free reaction proceeds via a one-pot cascade Michael addition/lactoniz

  生态友好的，直接的，和4-羟基香豆素三组分缩合/级联反应和（Ž）-azlactones到构建多元化二氢-5' ħ -螺[苯并[ C ^ ]苯并吡喃8,4'-唑] - 5'，6（7 H）-二酮作为新的被掩盖的氨基酸衍生物已被开发出来，具有高到极好的产率以及区域和非对映选择性。这种无金属的反应通过使用可重复使用的碳酸亚丙酯作为绿色溶剂的一锅级联迈克尔加成/内酯化/脱羧反应。还进行了放大检查，显示了在反应条件下的高原子经济性。此外，使用同位素标记，LC-MS监测和TLC-MALDI-MS进一步研究了反应机理。
• Oxazolone-Based Photoswitches: Synthesis and Properties
  作者：Marina Blanco-Lomas、Ignacio Funes-Ardoiz、Pedro J. Campos、Diego Sampedro

  DOI：10.1002/ejoc.201300641

  日期：2013.10

  synthesis, photophysics and photochemistry of a family of molecular switches inspired by the green fluorescent protein (GFP) chromophore is presented. These compounds can be synthesized in one step and good yields, their photophysical properties may be tuned by the substituents, solvent and wavelength of irradiation, and they show very efficient and fast photoisomerization. Furthermore, their high thermal

  介绍了受绿色荧光蛋白 (GFP) 生色团启发的一系列分子开关的合成、光物理学和光化学。这些化合物可以一步合成，产率高，它们的光物理性质可以通过取代基、溶剂和照射波长进行调节，并且它们表现出非常有效和快速的光异构化。此外，它们的高热稳定性和有限的光分解可以使这些开关用于一系列应用。最后，恶唑酮光开关可以通过使用光激活，并通过热或不同波长的光停用。
• Preferential formation of cis-4,5-dihydrooxazole derivatives via photoinduced electron transfer-initiated cyclization of N-acyl-α-dehydroarylalanine alkyl esters
  作者：Kei Maekawa、Norikazu Hishikawa、Kanji Kubo、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2007.08.089

  日期：2007.11

  aryl, and acyl substituent effects on the photoinduced electron transfer-initiated cyclization reaction of the title compounds (1) were investigated in polar solvents from mechanistic and synthetic points of view. The irradiation of (Z)-1 in methanol containing triethylamine (TEA) was found to quantitatively give cis- and trans-4,5-dihydrooxazole derivatives (cis-2 and trans-2). In addition to thermodynamic

  从机理和合成的观点出发，研究了极性溶剂中烷基，芳基和酰基取代基对标题化合物（1）的光诱导电子转移引发的环化反应的影响。的照射（ż） - 1在含有三乙胺（TEA）的甲醇被发现，定量得到顺式-和反式-4,5-二氢恶唑衍生物（顺式- 2和反式- 2）。除了热力学考虑为对发光强度的电子转移和荧光猝灭在TEA，酰基和芳基取代基效应的存在和光反应1证实了形成（E）-芳基亚甲基自由基阴离子和（E）-N-酰基自由基阴离子中间体的连续电子转移反应的参与。还证实了后者中间体的环化最终导致2。这样的发现为选择性的基础顺- 2大大随的烷基和芳基取代基的空间体积增加1，可以得出结论，在的环化双基中间，前体的这些取代基对氢移的空间位阻2负责该中间体的动力学控制的氢转移。产物组成分析表明，质子性极性溶剂甲醇具有氢键合溶剂化能力，是最适合检测的光环化反应的溶剂。
• 3-Isothiocyanato Oxindoles Serving as Powerful and Versatile Precursors to Structurally Diverse Dispirocyclic Thiopyrrolidineoxindoles through a Cascade Michael/Cyclization Process with Amino-Thiocarbamate Catalysts
  作者：Wen-Yong Han、Shi-Wu Li、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1002/chem.201300206

  日期：2013.4.26

  Cascading catalysis: 3‐Isothiocyanato oxindoles act as powerful and versatile precursors for a range of structurally diverse dispirocyclic thiopyrrolidineoxindoles containing two spiro‐quaternary and three contiguous stereogenic centers in quantitative yields with excellent disatereo‐ and enantioselectivities by only using 1 mol % amino‐thiocarbamate catalyst.

  级联催化：3-异硫氰酸根合吲哚是一系列结构多样的二螺环硫代吡咯烷并吲哚的有力且用途广泛的前体，仅使用1 mol％氨基硫代氨基甲酸酯催化剂，其定量收率就具有两个螺-季四和三个连续的立体中心，并具有优异的对映和对映选择性。 。