phenethyl 4-methylbenzoate | 203587-50-2

• 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: phenethyl 4-methylbenzoate
• 英文别名: p-Toluic acid, 2-phenylethyl ester；2-phenylethyl 4-methylbenzoate
• CAS: 203587-50-2
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: WSUBKOQJRDLGER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4-二甲基苯甲酸 在 4-methyl-3-(2,4,6-trimethylphenyl)thiazolium tetrafluoroborate 、 四丁基溴化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氘代乙腈 、 乙腈 为溶剂， 反应 36.0h， 生成 phenethyl 4-methylbenzoate
  参考文献：
  名称：

  Organocatalyzed Anodic Oxidation of Aldehydes

  摘要：

  A method for the catalytic formation of electroauxiliaries and subsequent anodic oxidation has been developed. The process interfaces N-heterocyclic carbene-based organocatalysis with electro-organic synthesis to achieve direct oxidation of catalytically generated electroactive intermediates. We demonstrate the applicability of this method as a one-pot conversion of aldehydes to esters for a broad range of aldehyde and alcohol substrates. Furthermore, the anodic oxidation reactions are very clean, producing only H-2 gas as a result of cathodic reduction.

  DOI：

  10.1021/ja304716r

文献信息

• From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)–C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air
  作者：Xiaoqiang Huang、Xinyao Li、Miancheng Zou、Song Song、Conghui Tang、Yizhi Yuan、Ning Jiao

  DOI：10.1021/ja5073004

  日期：2014.10.22

  The Cu-catalyzed aerobic oxidative esterification of simple ketones via C-C bond cleavage has been developed. Varieties of common ketones, even inactive aryl long-chain alkyl ketones, are selectively converted into esters. The reaction tolerates a wide range of alcohols, including primary and secondary alcohols, chiral alcohols with retention of the configuration, electron-deficient phenols, as well

  已经开发了通过 CC 键裂解的 Cu 催化的简单酮的有氧氧化酯化。各种常见的酮，甚至是惰性的芳基长链烷基酮，都被选择性地转化为酯。该反应耐受多种醇，包括伯醇和仲醇、保留构型的手性醇、缺电子酚以及各种天然醇。使用廉价的铜催化剂、广泛的基材范围以及中性和露天条件使该协议非常实用。(18)O 标记实验表明，在这种转化过程中发生了氧化作用。初步机制研究表明，该过程主要涉及两条新途径。
• Bis azide–triphenylphosphine as a reagent for esterification at room temperature
  作者：Murugan Dinesh、Sivasubramaniyan Archana、Raja Ranganathan、Murugan Sathishkumar、Alagusundaram Ponnuswamy

  DOI：10.1016/j.tetlet.2015.10.073

  日期：2015.12

  well-established reaction for the amide synthesis from organic azides and carboxylic acids in the presence of phosphorous reagents. In contrary to this, it is notable that bis azide in the presence of triethylphosphite or trimethylphosphite does not afford the expected bis amides but affords the ethyl or methyl esters of the carboxylic acids respectively. This serendipitous observation when further investigated

  改良的施陶丁格反应是在磷试剂存在下从有机叠氮化物和羧酸合成酰胺的公认方法。与此相反，值得注意的是，在亚磷酸三乙酯或亚磷酸三甲酯存在下的双叠氮化物不能提供预期的双酰胺，而是分别提供羧酸的乙酯或甲酯。当进一步研究时，这种偶然的观察结果导致发现了双叠氮化物-三苯基膦是室温下酯化的有效试剂。
• A microwave-assisted highly practical chemoselective esterification and amidation of carboxylic acids
  作者：Gunindra Pathak、Diparjun Das、Samuel Lalthazuala Rokhum

  DOI：10.1039/c6ra22558f

  日期：——

  The ubiquitousness of esters and amide functionalities makes their coupling reaction one of the most sought-after organic transformations. Herein, we have described an efficient microwave-assisted synthesis of esters and amides. Soluble triphenylphosphine, in conjugation with molecular iodine, gave the desired products without the requirement for a base/catalyst. In addition, a solid-phase synthetic

  酯和酰胺官能团无处不在，使它们的偶联反应成为最受欢迎的有机转化之一。在此，我们已经描述了酯和酰胺的有效微波辅助合成。可溶性三苯基膦与分子碘结合，可得到所需的产物，而无需碱/催化剂。另外，为所述转化引入了固相合成路线，其与溶液相路线相比具有更多的优点，例如低湿度敏感性，易于处理，通过简单过滤分离产物和可重复使用性。简而言之，我们的方法本质上是简单，温和，绿色和高度化学选择性的。
• Cu-Catalyzed Esterification Reaction via Aerobic Oxygenation and C–C Bond Cleavage: An Approach to α-Ketoesters
  作者：Chun Zhang、Peng Feng、Ning Jiao

  DOI：10.1021/ja4085463

  日期：2013.10.9

  The Cu-catalyzed novel aerobic oxidative esterification reaction of 1,3-diones for the synthesis of α-ketoesters has been developed. This method combines C-C σ-bond cleavage, dioxygen activation and oxidative C-H bond functionalization, as well as provides a practical, neutral, and mild synthetic approach to α-ketoesters which are important units in many biologically active compounds and useful precursors

  已开发出用于合成 α-酮酯的 Cu 催化的新型 1,3-二酮有氧氧化酯化反应。该方法结合了 CC σ-键裂解、双氧活化和氧化 CH 键功能化，并为 α-酮酯提供了一种实用、中性和温和的合成方法，α-酮酯是许多生物活性化合物中的重要单元和各种有用的前体。功能组转换。在机理研究的基础上提出了一个合理的激进过程。
• Sodium cyanide‐promoted copper‐catalysed aerobic oxidative synthesis of esters from aldehydes
  作者：Najmeh Nowrouzi、Mohammad Abbasi、Maryam Bagheri

  DOI：10.1002/aoc.3766

  日期：2017.11

  A simple and efficient copper‐catalysed procedure for oxidative esterification of aldehydes with alcohols and phenols mediated by sodium cyanide, using air as a clean oxidant, is described. A variety of aromatic aldehydes and structurally different alcohols and phenols reacted efficiently, and the product esters were obtained in good to excellent yields under normal atmospheric and solvent‐free conditions

  描述了一种简单有效的铜催化方法，该方法使用空气作为清洁氧化剂，通过氰化钠介导的醛与醇和酚的氧化酯化反应。各种芳族醛以及结构上不同的醇和酚都能有效地反应，在正常的大气压和无溶剂条件下，所获得的产物酯的收率好至极好。