isopropyl 2,4,6-trimethylbenzoate | 41589-61-1

• 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: isopropyl 2,4,6-trimethylbenzoate
• 英文别名: Isopropyl mesitylate；2,4,6-trimethyl-benzoic acid isopropyl ester；2,4,6-Trimethyl-benzoesaeure-isopropylester；2,4,6-Trimethylbenzoesaeure isopropylester；Isopropyl-2,4,6-trimethylbenzoat；Mesitoesaeureisopropylester；Propan-2-yl 2,4,6-trimethylbenzoate
• CAS: 41589-61-1
• 化学式: C₁₃H₁₈O₂
• mdl: MFCD20760884
• 分子量: 206.285
• InChiKey: TXYXHWDUMZSYCP-UHFFFAOYSA-N

物化性质

• 沸点：
  120.2-121 °C(Press: 6-6.5 Torr)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 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：

  2-碘代丙烷 、 2,4,6-三甲基苯甲酸 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 生成 isopropyl 2,4,6-trimethylbenzoate
  参考文献：
  名称：

  Preparation of hindered esters by the alkylation of carboxylate salts with simple alkyl halides

  摘要：

  DOI：

  10.1021/jo01328a019

文献信息

• Scope and Mechanistic Insights into the Use of Tetradecyl(trihexyl)phosphonium Bistriflimide: A Remarkably Selective Ionic Liquid Solvent for Substitution Reactions
  作者：James McNulty、Jerald J. Nair、Sreedhar Cheekoori、Vladimir Larichev、Alfredo Capretta、Al J. Robertson

  DOI：10.1002/chem.200600653

  日期：2006.12.13

  A survey of substitution reactions conducted in a phosphonium bistriflimide ionic liquid is presented. The results demonstrate high selectivity favoring substitution over typically competitive elimination and solvolytic processes even when challenging secondary and tertiary electrophiles are employed. The first reports of Kornblum substitution reactions in an ionic liquid are described that proceed

  提出了在b双酰亚胺化合物离子液体中进行的取代反应的综述。结果表明，即使采用具有挑战性的二级和三级亲电试剂，也比一般的竞争性消除和溶剂分解工艺具有更高的选择性替代性。描述了在离子液体中进行的Kornblum取代反应的第一个报道，该报道以非常高的化学选择性进行，有利于硝基而不是亚硝基产物和消除副产物。结构反应性研究表明，这些反应通过狭窄的途径进行，范围从直的S（N）2到沿着接近S（N）1极限的鞍点的预缔合途径。形成离解的碳阳离子的障碍归因于这种离子液体的结构特征，该结构特征有利于相关的亲核试剂的介入而不是离解，也防止了交叉进入E1过程。ist双酰亚胺化合物离子液体中缺少任何碱性实体似乎可以防止任何潜在的碱介导的消除反应，这使其成为用于一般取代反应的高度选择性的介质。
• A Novel Synthesis of Carboxylic Esters from 2-Methyl-4,6-pyrimidyl Dicarbonates and Grignard Reagents
  作者：Jae-In Lee

  DOI：10.5012/bkcs.2011.32.5.1765

  日期：2011.5.20

  2 equiv of carboxylic esters with organometallics. Inspired by our previous reports on ketones synthesis using pyrimidyl diesters, we investigated the synthesis of carboxylic esters from 2-methyl-4,6pyrimidyl dicarbonates and Grignard reagents. In choosing 2-methyl-4,6-pyrimidyl group as active moiety, we considered i) chelation effect between nitrogen atom and magnesium atom ii) thermal stability and

  羧酸酯主要通过羧酸或其衍生物与醇的反应来制备，并且已知大量的方法。然而，已经报道了一些关于通过α-碳和羰基碳之间形成σ键从有机金属的烷氧基羰基化衍生羧酸酯的方法。其中，炔基锂与氯甲酸甲酯或氯甲酸 2,2,2-三氯乙酯在低温下反应得到相应的 α,β-炔酸酯，但需要过量的氯甲酸酯试剂以避免竞争性副反应。尽管在 Pd 催化下用有机锰酸盐或与镁盐相关的有机铜试剂处理氯甲酸乙酯会产生相应的乙酯，这些有机金属化合物是通过额外的步骤制备的，范围分别限于伯基和烯基。格氏试剂与碳酸二烷基酯或氯甲酸烷基酯的直接烷氧基羰基化得到相应的酯，但前者需要 2 当量的碳酸二烷基酯，而后者仅限于在 -78 C 下制备 α-重氮酯。相反，格氏的烷氧基羰基化试剂与 1 equiv 的 2-碳酸吡啶酯反应良好，但 2,2,2-三氯乙酯的产率取决于反应温度。最近，氰基甲酸烷基酯已被用于有机金属的烷氧基羰基化。因此，炔基锂或烯基锂
• Esterification of Aromatic Carboxylic Acids with Alcohols Using 2-Chloro-3,5-dinitropyridine as a Condensing Agent
  作者：Seiji Takimoto、Naomi Abe、Yasushi Kodera、Hiroshi Ohta

  DOI：10.1246/bcsj.56.639

  日期：1983.2

  The reaction of 2-chloro-3,5-dinitropyridine (CDNP) with carboxylic acids and alcohols was examined, and it was found that CDNP was a useful condensing agent. Various esters were prepared in good yields.

  研究了 2-氯-3,5-二硝基吡啶 (CDNP) 与羧酸和醇的反应，发现 CDNP 是一种有用的缩合剂。以良好的收率制备了各种酯。
• A New Microwave Reactor for Batchwise Organic Synthesis
  作者：Kevin D. Raner、Christopher R. Strauss、Robert W. Trainor、John S. Thorn

  DOI：10.1021/jo00113a028

  日期：1995.4

  A laboratory-scale microwave batch reactor (MBR) has been developed for organic synthesis or kinetic studies on the 20-100 mt scale, with upper operating limits of 260 degrees C and 10 MPa (100 atm). The MBR complements a continuous microwave reactor which was the subject of a previous report from the authors' laboratory. Microwave-assisted organic reactions were conducted safely and conveniently in the MBR, for lengthy periods when required, and in volatile organic solvents. The use of water as a solvent for organic reactions was also explored. Examples include oxidation, elimination, esterifications, hydrolysis of a tertiary amide, etherification, isomerization, Hofmann elimination, alpha-iodination of a carboxylic acid, Claisen rearrangement, aminoreductone formation, and Wilgerodt reactions. Advantages of the new MBR include; the capability for rapid heating and quenching of reaction mixtures, minimal temperature gradients within the sample, and elimination of wall effects. Safety aspects have been discussed.
• A mild esterification process in phosphonium salt ionic liquid
  作者：James McNulty、Sreedhar Cheekoori、Jerald J. Nair、Vladimir Larichev、Alfredo Capretta、Al J. Robertson

  DOI：10.1016/j.tetlet.2005.03.169

  日期：2005.5

  A general, high yielding procedure is described for the esterification of carboxylic acids through carboxylate alkylation in phosphonium salt ionic liquid. (c) 2005 Elsevier Ltd. All rights reserved.