bis(2-methylbenzoyloxy)methane | 144168-19-4

• 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: bis(2-methylbenzoyloxy)methane
• 英文别名: bis-o-toluoyloxy-methane；Bis-o-toluoyloxy-methan；Methylen-di-o-toluat；(2-Methylbenzoyl)oxymethyl 2-methylbenzoate
• CAS: 144168-19-4
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: LHUVOYPMXWPQDS-UHFFFAOYSA-N

物化性质

• 沸点：
  423.4±33.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲苯甲酸 、 二氯甲烷 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以99%的产率得到bis(2-methylbenzoyloxy)methane
  参考文献：
  名称：

  Synthesis of esters from aldehydes or carboxylic acids with dichloromethane, dichloroethane or dichloropropane under mild conditions

  摘要：

  二氯甲烷（DCM）作为C1来源的新发现：DCM与羧酸或醛在TBHP水溶液中高效合成了亚甲基双酯。这些反应在温和条件下进行，能够以优异至极佳的产率（高达>99%）得到脂肪族和芳香族亚甲基双酯。同样的方法，可以从1,2-二氯乙烷和1,3-二氯丙烷分别容易地获得良好的至极佳产率的2-氯乙基苯甲酸酯和3-氯丙基苯甲酸酯。

  DOI：

  10.1039/c3ra43615b

文献信息

• Dichloromethane as a methylene synthon for regioselective linkage of diverse carboxylic acids: Direct access to methylene diesters under metal-free conditions
  作者：Shuiliang Wang、Zhengjiang Fu、Zhicong Huang、Yongqing Jiang、Shengmei Guo、Hu Cai

  DOI：10.1016/j.cclet.2019.04.053

  日期：2019.6

  Abstract A metal-free cross coupling between common CH2Cl2 and carboxylic acids has been achieved with K2CO3 as the sole additive. This simple protocol is a convenient and cost-effective route to synthesize methylene diesters from a wide scope of carboxylic acids substrates with good functional group tolerance. Several gram-scale reactions have been performed to evaluate the effectiveness and practicality

  摘要以碳酸钾为唯一添加剂，实现了普通二氯甲烷与羧酸之间的无金属交叉偶联。这个简单的协议是从具有良好官能团耐受性的各种羧酸底物合成亚甲基二酯的便捷且经济高效的途径。已经进行了数克级的反应，以评估该协议的有效性和实用性。
• Multicomponent Reaction: Palladium-Catalyzed Carbonylation of Aryl Halides and Alkyl Halides to Aromatic Esters
  作者：Fengxiang Zhu、Pengpeng Yin、Pengbo Zhang

  DOI：10.1021/acs.joc.2c01794

  日期：——

  A convenient four-component reaction has been developed that allows for the direct transformation of aryl iodides with alkyl halides into the corresponding aromatic esters and diesters via palladium-catalyzed carbonylation with water as solvent. Various esters and diesters were isolated in moderate to good yields with broad functional group tolerance.

  已经开发出一种方便的四组分反应，允许通过钯催化的以水为溶剂的羰基化将芳基碘与烷基卤化物直接转化为相应的芳族酯和二酯。各种酯和二酯以中等到良好的收率分离，具有广泛的官能团耐受性。
• Efficient Method for Synthesis of Methylene Diesters Using Polyethylene Glycol as a Phase Transfer Catalyst
  作者：Bhanudas P. Kavitake、Manikrao M. Salunkhe、Prakash P. Wadgaonkar

  DOI：10.1080/00397919708004081

  日期：1997.5

  Methylene diesters were synthesized in high yields at room temperature by reacting the potassium salt of a carboxylic acid with dibromo methane under the conditions of solid-liquid phase transfer catalysis using poly (ethylene glycol)-600 (PEG-600) as the phase transfer catalyst.