phthalic acid monophenethyl ester | 105578-59-4

• 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: phthalic acid monophenethyl ester
• 英文别名: 2-(2-Phenylethoxycarbonyl)benzoic acid
• CAS: 105578-59-4
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: KIBVCISKUNDXOE-UHFFFAOYSA-N

物化性质

• 沸点：
  466.5±38.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酐 生成 phthalic acid monophenethyl ester
  参考文献：
  名称：

  MODENA T.; PAVANETTO F.; CONTI B.; MAZZA M., FARMACO. ED. SCI., 41,(1986) N 9, 707-712

  摘要：

  DOI：

文献信息

• Controlled Release of Perfumery Alcohols by Neighboring-Group Participation. Comparison of the Rate Constants for the Alkaline Hydrolysis of 2-Acyl-, 2-(Hydroxymethyl)-, and 2-Carbamoylbenzoates
  作者：Jean-Yves de Saint Laumer、Eric Frérot、Andreas Herrmann

  DOI：10.1002/hlca.200390236

  日期：2003.8

  2-[(ethylamino)carbonyl]benzoates were found to have the highest rate constants for the alkaline ester hydrolysis, followed by unsubstituted 2-(aminocarbonyl)benzoates, or the corresponding isopropyl derivatives. To rationalize the influence of the different structural changes on the hydrolysis kinetics, the experimental data obtained for the 2-[(alkylamino)carbonyl]benzoates were compared with the

  一系列的2- acylbenzoates 1和2，2-（羟甲基）苯甲酸酯3，2-carbamoylbenzoates 4 - 6，以及氨基甲酰酯7或8分别的马来酸盐或琥珀酸盐，（参见图2），在制备几个反应步骤，并研究了这些化合物作为伯，仲和叔香料醇的受控释放的化学传递系统的潜在用途。通过肛门确定邻基团辅助的碱性酯水解的速率常数。在不同pH的H 2 O / MeCN缓冲溶液中进行HPLC （表1）。发现水解速率取决于醇的结构，前体骨架以及攻击酯功能的相邻亲核试剂的结构。伯醇的释放速度比仲醇和叔醇要快，而烯丙基伯醇（例如香叶醇）的苯甲酸酯的水解速度比同源饱和醇（如香茅醇）快2-4倍。对于相同的离去醇，环2-[（（乙基氨基）羰基]苯甲酸酯的环化速度比相应的2-（羟甲基）苯甲酸酯快，并且环化的速度比其2-甲酰基和2-乙酰基类似物快（例如，参见图4。）。在氨基甲酸酯系列中，发现2-[（（乙基氨基）羰
• Internal Catalysis in Covalent Adaptable Networks: Phthalate Monoester Transesterification As a Versatile Dynamic Cross-Linking Chemistry
  作者：Maarten Delahaye、Johan M. Winne、Filip E. Du Prez

  DOI：10.1021/jacs.9b07269

  日期：2019.9.25

  to the matrix and in close proximity to the dynamic bonds. In this context, we introduce the dynamic exchange of phthalate monoesters as a novel chemistry platform for covalent adaptable networks. A low MW model study shows that these monoesters undergo fast transesterification via a dissociative mechanism, caused by internal catalysis of the free carboxylic acid, which reversibly forms an activated

  共价适应性网络 (CAN) 通常利用高活性外部催化剂来提供动态化学键的快速交换。或者，当共价连接到基质并靠近动态键时，较温和的物质可以充当内部催化剂。在这种情况下，我们介绍了邻苯二甲酸酯单酯的动态交换作为共价适应性网络的新型化学平台。低 MW 模型研究表明，这些单酯通过游离羧酸的内部催化作用通过解离机制进行快速酯交换，从而可逆地形成活化的邻苯二甲酸酐中间体。使用这种动态化学，通过简单地固化二醇和三醇与双官能邻苯二甲酸酐的混合物，已经制备了一系列具有广泛特性的 CAN。通过多次循环的回收实验和使用流变学的应力松弛证实了网络的动态特性。网络被证明具有抗变形能力，但在其流变行为中表现出明显的温度响应，这与具有高活化能 (120 kJ/mol) 的快速交换反应有关。虽然可以获得具有低可溶性组分的密集交联和水解稳定的聚酯网络，但我们发现，通过在热溶剂中溶胀网络，发生了凝胶到溶胶的转变，导致网络完全溶
• Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Vijay D. Pawar、Yogesh S. Munot、Shieu-Shien Weng、Cheng-Hsiu Ku、Cheng-Yuan Liu

  DOI：10.1021/jo048363v

  日期：2005.2.1

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.
• Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate
  作者：Chien-Tien Chen、Jen-Huang Kuo、Chun-Hsin Li、N. B. Barhate、Sang-Wen Hon、Tai-Wei Li、Shi-Deh Chao、Chia-Cheng Liu、Ying-Chieh Li、I-Hsin Chang、Jin-Sheng Lin、Chin-Jing Liu、Y-Chen Chou

  DOI：10.1021/ol016684c

  日期：2001.11.1

  [GRAPHICS]Among four vanadyl species examined, vanadyl triflate was the most efficient catalyst to facilitate nucleophilic acyl substitution of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. By using mixed-anhydride technique, one can achieve oleate and peptide syntheses. In marked contrast to common metal triflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.
• Transesterification catalyzed by iron(III) β-diketonate species
  作者：Shiue-Shien Weng、Chih-Shueh Ke、Fong-Kuang Chen、You-Fu Lyu、Guan-Ying Lin

  DOI：10.1016/j.tet.2011.01.009

  日期：2011.3

  A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)(3) or other iron(III) beta-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric mu-alkoxy-bridged iron (III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron beta-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric mu-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)(2)(O-n-Bu)](2) derived from the alcoholysis of Fe(dbm)(3) under alkaline conditions. (C) 2011 Elsevier Ltd. All rights reserved.