2-methylphenacyl benzoate | 1220167-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methylphenacyl benzoate
• 英文别名: 2-oxo-2-(o-tolyl)ethyl benzoate；2-(Benzoyloxy)-5-methylacetophenone；[2-(2-methylphenyl)-2-oxoethyl] benzoate
• CAS: 1220167-08-7
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: DWCHENHRDQUMBL-UHFFFAOYSA-N

物化性质

• 沸点：
  422.0±28.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methylphenacyl benzoate 以 苯 为溶剂， 以100%的产率得到1-茚酮
  参考文献：
  名称：

  Unique solvent effect on photochemistry of ortho-alkylphenacyl benzoates

  摘要：

  Photolysis of 2,4,6-trialkylphenacyl benzoates gives not only the corresponding indanones and benzoic acid, but also the corresponding benzocyclobutenols (CBs), which are also detected in the photolysis of mono-alkylphenacyl benzoates for the first time. The product selectivity was heavily dependent upon solvents and o-alkyl group. H-bonding acceptor solvents strongly favor the formation of the CB. As the size of the o-alkyl group increases, the relative amount of the CB increases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.046
• 作为产物：
  描述：

  邻甲基苯甲酰氯 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 2-methylphenacyl benzoate
  参考文献：
  名称：

  通过光氧化还原催化 O-H 插入亚磺酰叶立德与羧酸构建 α-酰氧基酮

  摘要：

  在此，在温和简单的条件下进行了光氧化还原催化的亚砜叶立德与羧酸的插入，为制备具有广泛羧酸的α-酰氧基酮提供了一种实用的方法。实验和计算相结合的研究表明，该反应通过逐步质子辅助电子转移机制进行。

  DOI：

  10.1021/acs.orglett.3c02221

文献信息

• I₂/TBHP-mediated oxidative coupling of ketones and toluene derivatives: a facile method for the preparation of α-benzoyloxy ketones
  作者：Cui Chen、Weibing Liu、Peng Zhou、Hailing Liu

  DOI：10.1039/c7ra02298k

  日期：——

  An efficient oxidative approach was developed for the α-benzoyloxylation of ketones using tert-butyl hydroperoxide (TBHP). This process provided facile access to a wide range of α-benzoyloxy ketones in good to excellent yields via the direct oxidative α-benzoyloxylation of a structurally diverse series of ketones using simple arylmethane compounds.

  开发了一种使用叔丁基氢过氧化物（TBHP）进行酮的α-苯甲酰氧基化的有效氧化方法。通过使用简单的芳基甲烷化合物对一系列结构多样的酮进行直接氧化α-苯甲酰氧基化反应，该方法提供了以良好至极好的收率轻松获得各种α-苯甲酰氧基酮的方法。
• Temperature dependent product distribution in photolysis of o-alkylphenacyl benzoates
  作者：Mi Jang、Bum Hee Lim、Hyuk Jun Ryu、Bong Ser Park

  DOI：10.1016/j.tetlet.2013.10.109

  日期：2013.12

  Temperature effect on photochemical reactions of ortho-alkylphenacyl benzoates, one of the recently developed photoremovable protecting groups (PPG), giving indanones (IN) and benzocyclobutenols (CB) was examined. As temperature was lowered, CB was formed preferentially over IN and the amount of IN increased as temperature was elevated. Arrhenius plot of ln(IN/CB) versus 1/T gave a straight line from

  研究了温度对邻烷基苯甲酰基苯甲酸酯的光化学反应的影响，邻苯甲酰基苯甲酰苯甲酸酯是最近开发的光可去除保护基团（PPG），它具有茚满酮（IN）和苯并环丁烯醇（CB）。随着温度降低，CB优先于IN形成，并且IN的数量随温度升高而增加。ln（IN / CB）与1 / T的Arrhenius曲线给出了一条直线，从中可以得出Ea IN – Ea CB和A IN / A CB。受位阻最小的2-甲基苯甲酰苯甲酸甲酯（1）给出最高的Ea IN – Ea CB和甲IN /甲CB之间的邻-alkylphenacyl苯甲酸酯在此研究测试包括2,4,6- trimethylphenacyl苯甲酸酯（2）和2,4,6- triisopropylphenacyl苯甲酸甲酯（3）。
• Unique solvent effect on photochemistry of ortho-alkylphenacyl benzoates
  作者：Bong Ser Park、Hyuk Jun Ryu

  DOI：10.1016/j.tetlet.2010.01.046

  日期：2010.3

  Photolysis of 2,4,6-trialkylphenacyl benzoates gives not only the corresponding indanones and benzoic acid, but also the corresponding benzocyclobutenols (CBs), which are also detected in the photolysis of mono-alkylphenacyl benzoates for the first time. The product selectivity was heavily dependent upon solvents and o-alkyl group. H-bonding acceptor solvents strongly favor the formation of the CB. As the size of the o-alkyl group increases, the relative amount of the CB increases. (C) 2010 Elsevier Ltd. All rights reserved.
• Construction of α-Acyloxy Ketones via Photoredox-Catalyzed O–H Insertion of Sulfoxonium Ylides with Carboxylic Acids
  作者：Qing Sun、Yuzhu Peng、Yujing Wang、Xiaoguang Bao

  DOI：10.1021/acs.orglett.3c02221

  日期：2023.9.15

  sulfoxonium ylides with carboxylic acids was advanced under mild and simple conditions, offering a practical approach for preparing α-acyloxy ketones with a broad scope of carboxylic acids. A combined experimental and computational study suggests that this reaction proceeds via a stepwise proton-assisted electron transfer mechanism.

  在此，在温和简单的条件下进行了光氧化还原催化的亚砜叶立德与羧酸的插入，为制备具有广泛羧酸的α-酰氧基酮提供了一种实用的方法。实验和计算相结合的研究表明，该反应通过逐步质子辅助电子转移机制进行。