methyl 2-(2-methoxybenzoyl)benzoate | 40628-60-2

• 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: methyl 2-(2-methoxybenzoyl)benzoate
• CAS: 40628-60-2
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: GYUVTPHRFYUKKL-UHFFFAOYSA-N

物化性质

• 沸点：
  417.9±25.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-methoxybenzoyl)benzoate 在 环己胺 作用下， 以 乙腈 、 苯 为溶剂， 生成 methyl 2-[hydroxy-(2-methoxyphenyl)methyl]benzoate
  参考文献：
  名称：

  2-Benzoylbenzoic Acid:  A Photolabile Mask for Alcohols and Thiols

  摘要：

  Photolysis of 2-benzoylbenzoate esters of primary and secondary alcohols 1 in the presence of a hydrogen donor (2-isopropanol) or an electron donor (primary amines) produces the corresponding alcohol in high yield. The fate of the benzoate is dependent on the conditions used for the photoreaction. In 2-propanol, the ketyl radical that derives from photoreduction dimerizes, to afford the benzpinacol product 3,3'-diphenylbiphthalidyl, 5. In the presence of amines the product is 3-phenylphthalide, 6, a benzhydrol derivative which is the result of simple reduction of the ketone followed by lactonization. While the photoproduct of the benzoate-2-propanol reaction results from anticipated free radical chemistry, the amine-promoted reaction appears to result from a second, ''dark'', electron transfer process. We conclude that 2-benzoylbenzoic acid is an effective photolabile protecting group for primary and secondary alcohols, and preliminary studies indicate that thiols can be protected in an analogous way. Studies on the effect of benzophenone substituents and reaction solvent on the benzhydrol:benzpinacol product ratio provide mechanistic insight into the process.

  DOI：

  10.1021/jo961638p
• 作为产物：
  描述：

  2-溴苯甲醚 、 2-(氯羰基)苯甲酸甲酯 在 magnesium 作用下， 生成 methyl 2-(2-methoxybenzoyl)benzoate
  参考文献：
  名称：

  2-Benzoylbenzoic Acid:  A Photolabile Mask for Alcohols and Thiols

  摘要：

  Photolysis of 2-benzoylbenzoate esters of primary and secondary alcohols 1 in the presence of a hydrogen donor (2-isopropanol) or an electron donor (primary amines) produces the corresponding alcohol in high yield. The fate of the benzoate is dependent on the conditions used for the photoreaction. In 2-propanol, the ketyl radical that derives from photoreduction dimerizes, to afford the benzpinacol product 3,3'-diphenylbiphthalidyl, 5. In the presence of amines the product is 3-phenylphthalide, 6, a benzhydrol derivative which is the result of simple reduction of the ketone followed by lactonization. While the photoproduct of the benzoate-2-propanol reaction results from anticipated free radical chemistry, the amine-promoted reaction appears to result from a second, ''dark'', electron transfer process. We conclude that 2-benzoylbenzoic acid is an effective photolabile protecting group for primary and secondary alcohols, and preliminary studies indicate that thiols can be protected in an analogous way. Studies on the effect of benzophenone substituents and reaction solvent on the benzhydrol:benzpinacol product ratio provide mechanistic insight into the process.

  DOI：

  10.1021/jo961638p

文献信息

• Carbonylative Suzuki–Miyaura couplings of sterically hindered aryl halides: synthesis of 2-aroylbenzoate derivatives
  作者：Aya Ismael、Troels Skrydstrup、Annette Bayer

  DOI：10.1039/d0ob00044b

  日期：——

  diversely substituted 2-aroylbenzoate esters featuring a new protocol for the carbonylative coupling of aryl bromides with boronic acids and a new strategy to favour carbonylative over non-carbonylative reactions. Two different synthetic pathways - (i) the alkoxycarbonylation of 2-bromo benzophenones and (ii) the carbonylative Suzuki-Miyaura coupling of 2-bromobenzoate esters - were evaluated. The latter approach

  我们已经开发出一种羰基化方法，用于合成不同取代的2-芳基苯甲酸酯，其特征是芳基溴化物与硼酸进行羰基化偶联的新方案，以及采用羰基化而非非羰基化反应的新策略。评估了两种不同的合成途径-（i）2-溴二苯甲酮的烷氧基羰基化和（ii）2-溴苯甲酸酯的羰基化Suzuki-Miyaura偶联-。后一种方法提供了更宽的基材耐受性，因此是首选途径。我们观察到2-取代的芳基溴化物是具有挑战性的羰基化化学底物，有利于非羰基化途径。但是，我们发现，缓慢添加硼酸可以改善羰基化的Suzuki-Miyaura偶联，
• Rigaudy,J.; Sparfel,D., Bulletin de la Societe Chimique de France, 1972, p. 3441 - 3446
  作者：Rigaudy,J.、Sparfel,D.

  DOI：——

  日期：——
• 2-Benzoylbenzoic Acid:  A Photolabile Mask for Alcohols and Thiols
  作者：Paul B. Jones、Michael P. Pollastri、Ned A. Porter

  DOI：10.1021/jo961638p

  日期：1996.1.1

  Photolysis of 2-benzoylbenzoate esters of primary and secondary alcohols 1 in the presence of a hydrogen donor (2-isopropanol) or an electron donor (primary amines) produces the corresponding alcohol in high yield. The fate of the benzoate is dependent on the conditions used for the photoreaction. In 2-propanol, the ketyl radical that derives from photoreduction dimerizes, to afford the benzpinacol product 3,3'-diphenylbiphthalidyl, 5. In the presence of amines the product is 3-phenylphthalide, 6, a benzhydrol derivative which is the result of simple reduction of the ketone followed by lactonization. While the photoproduct of the benzoate-2-propanol reaction results from anticipated free radical chemistry, the amine-promoted reaction appears to result from a second, ''dark'', electron transfer process. We conclude that 2-benzoylbenzoic acid is an effective photolabile protecting group for primary and secondary alcohols, and preliminary studies indicate that thiols can be protected in an analogous way. Studies on the effect of benzophenone substituents and reaction solvent on the benzhydrol:benzpinacol product ratio provide mechanistic insight into the process.