ethyl p-cyanophenyl carbonate | 77637-90-2

• 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 p-cyanophenyl carbonate
• 英文别名: ethyl 4-cyanophenyl carbonate；Carbonic acid, ethyl 4-cyanophenyl ester；(4-cyanophenyl) ethyl carbonate
• CAS: 77637-90-2
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: QBQRNAOYCNQVFL-UHFFFAOYSA-N

物化性质

• 沸点：
  319.9±34.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• 保留指数：
  1541

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl p-cyanophenyl carbonate 在 吡啶 、 phosphate buffer 作用下， 生成 4-羟基苯甲腈
  参考文献：
  名称：

  Effect of nucleophile basicity on intramolecular nucleophilic aminolysis reactions of carbonate diesters

  摘要：

  DOI：

  10.1021/ja00404a036
• 作为产物：
  描述：

  4-羟基苯甲腈 、 焦碳酸二乙酯 在 magnesium(II) perchlorate 作用下， 反应 4.5h， 以97%的产率得到ethyl p-cyanophenyl carbonate
  参考文献：
  名称：

  在高氯酸镁促进的无溶剂条件下制备碳酸芳乙酯的一种新的、温和的、通用的和有效的途径

  摘要：

  报告了一种新的、通用的、温和的方法，用于直接合成由路易斯酸促进的芳基和烷基乙基碳酸酯。在 Mg(ClO4)2（一种 1,3-二羰基化合物的特定活化剂）存在下，该反应与二碳酸二乙酯平稳进行，并显示出普遍适用性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600366

文献信息

• Metal nitrate promoted highly regiospecific <i>ortho</i>–nitration of phenols: Application to the synthesis of nitroxynil
  作者：Zafar Iqbal、Asha Joshi、Saroj Ranjan De

  DOI：10.1080/00397911.2023.2184270

  日期：2023.4.18

  Abstract Highly regiospecific ortho–nitration of electronically diverse phenols is accomplished using Fe(NO3)3.9H2O for electron–rich and Cu(NO3)2.6H2O for electron–deficient phenols as the cheap nitrating agents. The reaction is carried out in CH3CN at 90 °C under mild and neutral conditions where structurally diverse phenols afford exclusively ortho–nitration products in moderate to good yields with

  摘要 使用 Fe(NO 3 ) 3 .9H 2 O 富电子酚和 Cu(NO 3 ) 2 .6H 2 O 缺电子酚作为廉价的硝化剂，实现电子多样性酚类的高度区域特异性邻位硝化。该反应在 CH 3 CN 中于 90 °C 在温和和中性的条件下进行，其中结构多样的酚类以中等到良好的收率专门提供邻硝化产物，并且具有出色的官能团耐受性。通过实现生物活性化合物硝苯腈，建立了该策略的合成应用。
• Concerted Mechanisms of the Reactions of Ethyl <i>S</i>-Aryl Thiocarbonates with Substituted Phenoxide Ions
  作者：Enrique A. Castro、Paulina Pavez、José G. Santos

  DOI：10.1021/jo981956j

  日期：1999.4.1

  The reactions of 4-nitrophenyl, 2,4-dinitrophenyl, and 2,4,6-trinitrophenyl O-ethyl thiolcarbonates with substituted phenoxide ions are subjected to a kinetic study in water, 25.0 degrees C, ionic strength 0.2 M (KCl). By following the reactions spectrophotometrically, pseudo-first-order rate coefficients (k(obsd)) are found under excess of the nucleophile. Plots of k(obsd) VS phenoxide anion concentration at constant pH are linear, with the slope (k(N)) independent of pH. The Bronsted-type plots (log kN vs pK(a) of the phenols) are linear with slopes beta = 0.92, 0.77, and 0.61 for the reactions of the 4-nitrophenyl, 2,4-dinitrophenyl, and 2,4,6-trinitrophenyl derivatives, respectively. For these reactions, a concerted mechanism is proposed since the slope values are similar to those found in the concerted phenolysis of aryl acetates; the slope magnitudes are not consistent with a stepwise mechanism where the formation of a tetrahedral intermediate is rate limiting. Our results are in line with the finding that the reactions of the 2,4-dinitrophenyl and 2,4,6-trinitrophenyl derivatives with secondary alicyclic amines in water are concerted. In contrast, the reactions of the same substrates with pyridines are stepwise, which means that substitution of a pyridine moiety in a tetrahedral intermediate with a benzenethio group by a phenoxy group destabilizes the intermediate.