ethyl α-hydroxy-α-(4-nitrophenyl)-α-phenylacetate | 81039-87-4

• 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 α-hydroxy-α-(4-nitrophenyl)-α-phenylacetate
• 英文别名: ethyl 2-hydroxy-2-(4-nitrophenyl)-2-phenylacetate
• CAS: 81039-87-4
• 化学式: C₁₆H₁₅NO₅
• 分子量: 301.299
• InChiKey: QTHQRKZCQRJKFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl α-hydroxy-α-(4-nitrophenyl)-α-phenylacetate 在 Pd-polyethylamine 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到ethyl α-hydroxy-α-(4-aminophenyl)-α-phenylacetate
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]oct-3-yl .alpha.-hydroxy-.alpha.-(4-iodophenyl)-.alpha.-phenylacetate as potential radiopharmaceuticals

  摘要：

  Two derivatives of (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.

  DOI：

  10.1021/jm00368a009
• 作为产物：
  描述：

  ethyl 2-(diethoxyphosphoryloxy)-2-(4-nitrophenyl)-2-phenylacetate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以79%的产率得到ethyl α-hydroxy-α-(4-nitrophenyl)-α-phenylacetate
  参考文献：
  名称：

  基于Umpolung策略的α-酮酸酯的有机催化丙烯酸化：磷腈催化的SNAr反应，利用[1,2]-磷-布鲁克重排

  摘要：

  α-酮酸酯的有机催化芳基化反应是基于umpolung策略开发的。磷腈P2- t Bu有效催化α-酮酸酯，甲硅烷基化的亚磷酸酯和缺电子的氟代芳烃的三组分偶联反应，从而提供在α-位置具有缺电子的芳基的α-羟基酯衍生物。该反应涉及通过[1,2]-磷-布鲁克重排反应，由α-酮酸酯催化生成α-氧化酯烯酸酯，然后进行S N Ar反应。

  DOI：

  10.1002/chem.201803218

文献信息

• The facile synthesis of α-aryl-α-hydroxy esters via one-pot vicarious nucleophilic substitution and oxidation
  作者：Nicholas J. Lawrence、Olivier Lamarche、Nabil Thurrab

  DOI：10.1039/a900986h

  日期：——

  The anion produced by the vicarious nucleophilic substitution reaction of nitroarenes and α-chloro esters is hydroxylated by the action of air and benzaldehyde, thereby producing α-hydroxy esters.

  由硝基芳烃和α-氯酯的替代亲核反应产生的阴离子在空气和苯甲醛的作用下被羟基化，从而生成α-羟基酯。
• Transition-Metal-Free Regiospecific Aroylation of Nitroarenes Using Ethyl Arylacetates at Room Temperature
  作者：Promod Kumar、Anup Kumar Sharma、Tirumaleswararao Guntreddi、Rahul Singh、Krishna Nand Singh

  DOI：10.1021/acs.orglett.7b03882

  日期：2018.2.2

  A novel regiospecific C(sp(3))-C(sp(2)) coupling between ethyl arylacetates and nitroarenes has been developed to deliver biaryl ketones in excellent yields. The protocol is metal-free, mild, and compatible with a number of functional groups on both of the reacting partners.