ethyl 3-cyano-4-phenylbenzoate | 1309921-09-2

• 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: ethyl 3-cyano-4-phenylbenzoate
• CAS: 1309921-09-2
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: NMQDVLZCXVRILP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-cyano-4-phenylbenzoate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-氰基-4-联苯羧酸
  参考文献：
  名称：

  Design and synthesis of substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides as positive allosteric modulators of the metabotropic glutamate receptor subtype 5

  摘要：

  Based on SAR in the alkyne class of mGlu5 receptor negative allosteric modulators and a set of amide-based positive allosteric modulators, optimized substitution of the aryl 'b' ring was used to create substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides. Results from an mGlu5 receptor functional assay, using calcium fluorescence, revealed varying efficacies and potencies that provide evidence that subtle changes in compounds within a close structural class can have marked effects on functional activity including switches in modes of efficacy (i.e., negative to positive allosteric modulation). Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.12.110
• 作为产物：
  描述：

  4-羟基-3-碘苯甲酸乙酯 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 28.5h， 生成 ethyl 3-cyano-4-phenylbenzoate
  参考文献：
  名称：

  Synthesis and evaluation of 1,2,4-methyltriazines as mGluR5 antagonists

  摘要：

  在前期的研究中，我们展示了3-(取代苯乙炔基)-5-甲基[1,2,4]三嗪类类似物MPEP是谷氨酸介导的细胞内钙动员的强效拮抗剂，通过mGluR5体外效力检测。在本研究中，我们报道了六种3-(取代联苯乙炔基)-5-甲基[1,2,4]三嗪（5a–f）和五种3-(取代苯氧基苯乙炔基)-5-甲基三嗪（6a–e）的合成与评估。化合物2-(4-氟苯基)-5-[2-(5-甲基[1,2,4]三嗪-3-基)乙炔基]苯腈（5f），其IC50值为28.2 nM，是其中效力最强的类似物。

  DOI：

  10.1039/c0ob01190h

文献信息

• Metal-Free Generation of γ-Cyanoalkyl Radicals by N-Heterocyclic Carbene Catalysis: Assembly of 6-Cyanoalkyl Phenanthridines
  作者：Qianrong Li、Cong-Ying Zhou、Chengming Wang

  DOI：10.1021/acs.orglett.2c03808

  日期：2022.12.23

  number of γ-cyanoalkyl radicals were generated by sustainable N-heterocyclic carbene catalysis in tin-, transition-meal-, and light-free conditions, followed by insertion into biaryl isonitriles, thus leading to the rapid assembly of a variety of diversely functionalized 6-cyanoalkyl phenanthridines. A preliminary mechanism study revealed that a single-electron transfer radical process was possibly involved

  在无锡​​、过渡餐和无光条件下，通过可持续的 N-杂环卡宾催化产生了许多 γ-氰基烷基自由基，然后插入到联芳基异腈中，从而导致各种不同功能化的快速组装6-氰基烷基菲啶。初步的机理研究表明，可能涉及单电子转移自由基过程。
• Design and synthesis of substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides as positive allosteric modulators of the metabotropic glutamate receptor subtype 5
  作者：Mu-Fa Zou、Jianjing Cao、Alice L. Rodriguez、P. Jeffrey Conn、Amy Hauck Newman

  DOI：10.1016/j.bmcl.2010.12.110

  日期：2011.5

  Based on SAR in the alkyne class of mGlu5 receptor negative allosteric modulators and a set of amide-based positive allosteric modulators, optimized substitution of the aryl 'b' ring was used to create substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides. Results from an mGlu5 receptor functional assay, using calcium fluorescence, revealed varying efficacies and potencies that provide evidence that subtle changes in compounds within a close structural class can have marked effects on functional activity including switches in modes of efficacy (i.e., negative to positive allosteric modulation). Published by Elsevier Ltd.
• Synthesis and evaluation of 1,2,4-methyltriazines as mGluR5 antagonists
  作者：Jeremy P. Olson、Moses G. Gichinga、Elizabeth Butala、Hernan A. Navarro、Brian P. Gilmour、F. Ivy Carroll

  DOI：10.1039/c0ob01190h

  日期：——

  In previous studies we showed that 3-(substituted phenylethynyl)-5-methyl[1,2,4]triazine analogues of MPEP were potent antagonists of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro efficacy assay. In the present study we report the synthesis and evaluation of six 3-(substituted biphenylethynyl)-5-methyl[1,2,4]triazines (5a–f), and five 3-(substituted phenoxyphenylethynyl)-5-methyltriazines (6a–e). Compound 2-(4-fluorophenyl-5-[2-(5-methyl[1,2,4]triazine-3-yl)ethynyl]benzonitrile (5f) with an IC50 of 28.2 nM was the most potent analogue.

  在前期的研究中，我们展示了3-(取代苯乙炔基)-5-甲基[1,2,4]三嗪类类似物MPEP是谷氨酸介导的细胞内钙动员的强效拮抗剂，通过mGluR5体外效力检测。在本研究中，我们报道了六种3-(取代联苯乙炔基)-5-甲基[1,2,4]三嗪（5a–f）和五种3-(取代苯氧基苯乙炔基)-5-甲基三嗪（6a–e）的合成与评估。化合物2-(4-氟苯基)-5-[2-(5-甲基[1,2,4]三嗪-3-基)乙炔基]苯腈（5f），其IC50值为28.2 nM，是其中效力最强的类似物。