ethylene glycol di-para-cyanobenzoate | 117615-43-7

• 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: ethylene glycol di-para-cyanobenzoate
• 英文别名: 2-(4-Cyanobenzoyl)oxyethyl 4-cyanobenzoate
• CAS: 117615-43-7
• 化学式: C₁₈H₁₂N₂O₄
• 分子量: 320.304
• InChiKey: HQEVZXHMPRDAJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对氰基苯甲酰氯 、 乙二醇 在 吡啶 作用下， 生成 ethylene glycol di-para-cyanobenzoate
  参考文献：
  名称：

  Deguire, Suzanne; Brisse, Francois, Canadian Journal of Chemistry, 1988, vol. 66, p. 2545 - 2552

  摘要：

  DOI：

文献信息

• Deguire, Suzanne; Brisse, Francois, Canadian Journal of Chemistry, 1988, vol. 66, p. 2545 - 2552
  作者：Deguire, Suzanne、Brisse, Francois

  DOI：——

  日期：——
• Reduction of Diesters of 1,2-Diols. Regioselective C−O Bond Cleavage of the Anionic Forms
  作者：Norma A. Macías-Ruvalcaba、Cheryl L. Moy、Zi-Rong Zheng、Dennis H. Evans

  DOI：10.1021/jo060535w

  日期：2006.6.1

  [GRAPHICS]The electrochemical reduction of benzoate diesters of glycols has been studied in acetonitrile and N, N-dimethylformamide as solvents. The reductions occur in two closely spaced one-electron steps, and it was found that the dianion diradicals decompose by one of two routes, depending on the substituents on the ethylene moiety: cleavage of two benzoates to produce alkene or formation of benzil by way of a postulated cyclic intermediate to produce also the dianion of the diol. These correspond to cleavage of the R-OC( O) Ar bonds and the RO-C( O) Ar bonds, respectively. When the radical formed by the former cleavage is a primary or secondary radical, the reaction is too slow to compete with the latter reaction that produces benzil. However, when that radical is either tertiary or benzylic, the former cleavage reaction is fast and no benzil is detected. The dianions of p-cyano-and p-nitrobenzoate esters are rather stable on the voltammetric time scale. However, the addition of lithium ions results in detectable formation of 4,4'-dicyanobenzil from four different p-cyanobenzoate diesters.