3-chlorophenyl benzoate | 13189-55-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 3-chlorophenyl benzoate
• 英文别名: Benzoic acid m-chlorophenyl ester；(3-chlorophenyl) benzoate
• CAS: 13189-55-4
• 化学式: C₁₃H₉ClO₂
• mdl: MFCD00622431
• 分子量: 232.666
• InChiKey: PMARQWWQXBASSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916310090

反应信息

• 作为反应物：
  描述：

  3-chlorophenyl benzoate 以58%的产率得到
  参考文献：
  名称：

  BHAVSAR, MADHURY D.;DESAI, VIJAYKANT B., MAN-MADE TEXT. INDIA , 32,(1989) N, C. 8-11, 15

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酸 在 双氧水 、 potassium carbonate 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 生成 3-chlorophenyl benzoate
  参考文献：
  名称：

  烯醇酯中间诱导的羧酸和芳基硼酸的无金属氧化偶联

  摘要：

  使用丙酸甲酯作为活化剂已成功开发了羧酸与芳基硼酸的直接酯化。这种转化是通过烯醇酯中间体诱导的无金属氧化偶联过程完成的。无金属，操作简单，对官能团的耐受性好，所有这些都表明该方法是形成酚酯的一种可采用的方法。

  DOI：

  10.1002/ejoc.201900137
• 作为试剂：
  描述：

  丙二酸环(亚)异丙酯 、 对氯碘苯 在 3-chlorophenyl benzoate 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以31 %的产率得到2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-(4-chlorophenyl)iodonium ylide
  参考文献：
  名称：

  On the Risk of ¹⁸F-Regioisomer Formation in the Copper-Free Radiofluorination of Aryliodonium Precursors

  摘要：

  DOI：

  10.1021/acs.orglett.3c03499

文献信息

• Determination of aromaticity indices of thiophene and furan by nuclear magnetic resonance spectroscopic analysis of their phenyl esters
  作者：Chang Kiu Lee、Ji Sook Yu、Hye-Jin Lee

  DOI：10.1002/jhet.5570390615

  日期：2002.11

  series of m- and p-substituted phenyl benzoates, 2-thienoates, and 2-furoates were prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shift values of protons and carbons of the acyl aromatic rings and the Hammett σ. Plots of the chemical shift values of the carbonyl carbons of the benzoates against those of

  一系列的米-和p取代的苯基苯甲酸酯，2- thienoates和2-糠酸盐，制备和它们的1个H和13进行了检查C NMR光谱特征。通常，在酰基芳环的质子和碳的化学位移值与哈米特σ之间观察到良好的相关性。苯甲酸酯的羰基碳的化学位移值与2-硫代酸酯和2-糠酸酯的化学位移图具有极好的相关性，在二甲基亚砜-d 6和0.90和0.90中斜率值分别为0.85和0.75。氯仿中d分别为0.78 。该值可以被认为是一组芳香性指数。
• Ligand‐Controlled C−O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights
  作者：Li Li、Feifei Song、Xiumei Zhong、Yun‐Dong Wu、Xinhao Zhang、Jiean Chen、Yong Huang

  DOI：10.1002/adsc.201901136

  日期：2020.1.7

  Palladium‐catalyzed cross‐coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C−C bond coupling and C−H arylation are well established in the literature. However, direct C−O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C−O bond formation,

  羧酸与芳基卤化物之间的钯催化交叉偶联反应有几种可能的竞争途径。脱羧CC键偶联和CH芳基化在文献中已得到很好的建立。但是，羧酸与芳基卤化物之间的直接C-O键偶联几乎没有成功。在本报告中，我们描述了由双齿N，N-配体（例如1,10-菲咯啉）实现的排他性C-O键形成的协议。该反应通常适用于多种羧酸和碘代芳烃。实验证据和计算结果表明，脱羧碳-碳键偶联的替代途径具有较高的能垒。
• Kinetics and Mechanism of Nucleophilic Displacement Reactions of Y-Substituted Phenyl Benzoates with Cyanide Ion
  作者：Song-I Kim、Eun-Hee Kim、Ik-Hwan Um

  DOI：10.5012/bkcs.2010.31.03.689

  日期：2010.3.20

  Discussion The kinetic study was performed spectrophotometrically. All reactions proceeded with quantitative liberation of Y-substituted phenoxide ion (and/or its conjugate acid) under pseudo-first- order conditions (i.e., the nucleophile concentration in excess over the substrate concentration). The reactions obeyed first- order kinetics and pseudo-first-order rate constants (

  Y 取代苯甲酸苯酯 (1) 和苯硫代苯甲酸苯酯 (2) 与 CN 反应的二级速率常数汇总 - 在 80 mol % H 2 O/20 mol % DMSO 中，温度为 25.0 ± 0.1 o C a entry Y p K a 10 2 k CN- / M –1 s –1 12a 4-MeO 10.20 0.843 b 2.13 b 4-Me 10.19 0.783 b 1.89 c 3-CH 3 10.08 0.724 - d H 9.95 1.02 b 2.75 e 4-Cl 9.38 2.32 - f 3-COMe 9.19 3.59 b - g 3-Cl 9.02 4.19 - h 3-CHO 8.98 3.93 - i 4-COOEt 8.50 6.07 - j 3-NO 2 8.35 14.1 b 18.0 k 4-COMe 8.05 7.68 b 7.88 l 4-CN 7
• Studies of reactions within molecular complexes: alkaline hydrolysis of substituted phenyl benzoates in the presence of xanthines
  作者：Necmettin Pirinccioglu、Andrew Williams

  DOI：10.1039/a705499h

  日期：——

  Complexation with caffeine and theophylline-7-acetate depresses the rate of alkaline hydrolysis of substituted phenyl benzoates and is consistent with the formation of molecular complexes with 1∶1 stoichiometry between the hosts and esters; stacking of the xanthines is excluded as an explanation in the range of concentrations studied. Brønsted-type correlations have been determined for the rate and complexation constants and for the transition-state binding constants. Development of effective charge in the transition state of the reactions in bulk solvent is slightly less than that in the host–ester complex, consistent with a similar electronic environment in both states. The negative Brønsted β values for KS indicate that the interactions between ester and hosts involve electron donation to the host from the ester. Inhibition of hydrolysis is attributed to repulsion of the hydroxide ion from the host–ester complex by the extra hydrophobicity engendered by the xanthine host, as well as by the weaker binding of the transition state to the host compared with that in the host–ester complex.

  咖啡因和茶碱-7-乙酸酯与取代苯基苯甲酸酯的络合作用降低了其碱水解速率，并与主体和酯之间形成1∶1化学计量比的分子络合物的观点一致；在研究的浓度范围内，排除了黄嘌呤的堆叠作为解释。已确定速率常数、络合常数和过渡态结合常数的Brønsted型相关性。反应在体溶剂过渡态的有效电荷发展略低于主体-酯络合物中的情况，这与两种状态下类似的电子环境一致。Brønsted负β值对于KS表明，酯与主体之间的相互作用涉及酯向主体的电子捐赠。水解的抑制归因于由黄嘌呤主体产生的额外疏水性，使得羟基离子被排斥出主体-酯络合物，以及与主机-酯络合物相比，过渡态与主体的结合较弱。
• A Novel Synthesis of Phenyl Carboxylates
  作者：Shizunobu Hashimoto、Isao Furukawa

  DOI：10.1246/bcsj.54.2227

  日期：1981.7

  The direct synthesis of phenyl carboxylates from phenols and carboxylic acids is reported. The reactions proceeded easily when triphenylphosphine and carbon tetrachloride were used as dehydrating agents in the presence of a tertiary amine at room temperature, thus giving esters in high yields.

  报道了从苯酚和羧酸直接合成苯基羧酸盐。在室温下，在叔胺存在下，以三苯基膦和四氯化碳为脱水剂，反应容易进行，从而得到高产率的酯。