3-(3-phenoxyphenyl)-2-acrylonitrile | 1185760-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-phenoxyphenyl)-2-acrylonitrile
• 英文别名: 3-(3-phenoxyphenyl)propenonitrile；3-(3-Phenoxyphenyl)-propenonitrile；3-(3-phenoxyphenyl)prop-2-enenitrile
• CAS: 1185760-63-7
• 化学式: C₁₅H₁₁NO
• mdl: MFCD16506009
• 分子量: 221.258
• InChiKey: GLNCKCDTJSYLAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-phenoxyphenyl)-2-acrylonitrile 在 盐酸 、 三(五氟苯基)硼烷 作用下， 以 乙醚 、 氘代氯仿 为溶剂， 反应 36.0h， 生成 N-[2-(diphenylsilyl)-3-(3-phenoxyphenyl)propyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  无金属催化条件下共轭腈的化学选择性甲硅烷基化还原：β-甲硅烷基胺和烯胺

  摘要：

  已开发出B（C 6 F 5）3催化的共轭腈的甲硅烷基化还原反应，以提供具有合成价值的β-甲硅烷基胺。该反应是化学选择性的，并且在温和的条件下进行。机理说明表明，它是通过将共轭腈快速双氢化硅烷化成烯胺中间体进行的，烯胺中间体随后被还原为β-甲硅烷基胺，从而形成一个新的C（sp 3）Si键。基于这种机理上的理解，还使用大体积的硅烷建立了制备烯胺的制备途径。

  DOI：

  10.1002/anie.201502366
• 作为产物：
  描述：

  氰甲基磷酸二乙酯 、 间苯氧基苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-(3-phenoxyphenyl)-2-acrylonitrile
  参考文献：
  名称：

  高效稳定的Vγ9Vδ2 T细胞的小分子激动剂

  摘要：

  本发明涉及式(I)化合物作为高效稳定的Vγ9Vδ2 T细胞的小分子激动剂，其中各基团定义如说明书和权利要求书所详述。本发明还涉及含有式(I)化合物的药物组合物以及它们在治疗增殖性疾病中的用途。

  公开号：

  CN109651429A

文献信息

• Synthesis of new derivatives of diphenyl oxide
  作者：Yu. V. Popov、T. K. Korchagina、V. S. Kamaletdinova

  DOI：10.1134/s1070363210030163

  日期：2010.3

  Studying of chemical properties of nitriles containing diphenyl oxide fragment in their structure opens wide prospects for obtaining new compounds possessing various chemical and pharmacological properties. They can be used as biologically active substances and ingredients of rubber mixtures of polyfunctional action. Effective synthetic approaches to imidate hydrochlorides, N-substituted imidates,

  对结构中含有二苯醚片段的腈的化学性质的研究为获得具有各种化学和药理性质的新化合物打开了广阔的前景。它们可以用作生物活性物质和具有多官能作用的橡胶混合物的成分。从相应的腈类化合物（如3-（3-苯氧基苯基）-2-丙烯腈，3-（3-苯氧基苯基）-2-丁烯腈），亚硝酸盐酸盐，N-取代的酰亚胺盐和含3-苯氧基苯基片段的am开发了有效的合成方法。和2-甲基-2-（3-苯氧基苄氧基）丙腈。
• Inhibition of Staphyloxanthin Virulence Factor Biosynthesis in <i>Staphylococcus aureus</i>: In Vitro, in Vivo, and Crystallographic Results
  作者：Yongcheng Song、Chia-I Liu、Fu-Yang Lin、Joo Hwan No、Mary Hensler、Yi-Liang Liu、Wen-Yih Jeng、Jennifer Low、George Y. Liu、Victor Nizet、Andrew H.-J. Wang、Eric Oldfield

  DOI：10.1021/jm9001764

  日期：2009.7.9

  The gold color of Staphylococcus aureus is derived from the carotenoid staphyloxanthin, a virulence factor for the organism. Here, we report the synthesis and activity of a broad variety of staphyloxanthin biosynthesis inhibitors that inhibit the first committed step in its biosynthesis, condensation of two farnesyl diphosphate (FPP) molecules to dehydrosqualene, catalyzed by the enzyme dehydrosqualene synthase (CrtM). The most active compounds are phosphonoacetamides that have low nanomolar K-i values for CrtM inhibition and are active in whole bacterial cells and in mice, where they inhibit S. aureus disease progression. We also report the X-ray crystallographic structure of the most active compound, N-3-(3-phenoxyphenyl)propylphosphonoacetamide (IC50 = 8 nM, in cells), bound to CrtM. The structure exhibits a complex network of hydrogen bonds between the polar headgroup and the protein, while the 3-phenoxyphenyl side chain is located in a hydrophobic pocket previously reported to bind farnesyl thiodiphosphate (FsPP), as well as biphenyl phosphonosulfonate inhibitors. Given the good enzymatic, whole cell, and in vivo pharmacologic activities, these results should help guide the further development of novel antivirulence factor-based therapies for S. aureus infections.
• Synthesis of nitriles containing 3-phenoxyphenyl fragment
  作者：Yu. V. Popov、T. G. Korchagina、V. S. Kamaletdinova

  DOI：10.1134/s107036321004016x

  日期：2010.4

  Reactions of the aldol-crotonic condensation, acylation of acetonitrile, and addition of amine to the activated double bond of acrylonitrile in the series of diphenyl oxide derivatives are studied. Effective procedures for preparing the nitriles containing diphenyl oxide fragment like 3-(3-phenoxyphenyl)-propenonitrile, 3-(3-phenoxyphenyl)-2-butenonitrile, 3-phenoxybenzoylacetonitrile, 3-(3-phenoxyphenyl)-propionitrile, and 3-phenoxybenzylamino)propionitrile are developed.