2-(2-甲基苯基)-2-氧代乙基甲烷磺酸酯 | 799804-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(2-甲基苯基)-2-氧代乙基甲烷磺酸酯
• 英文名称: 2-mesyloxy-1-(2-methylphenyl)-1-ethanone
• 英文别名: Ethanone, 1-(2-methylphenyl)-2-[(methylsulfonyl)oxy]-；[2-(2-methylphenyl)-2-oxoethyl] methanesulfonate
• CAS: 799804-23-2
• 化学式: C₁₀H₁₂O₄S
• 分子量: 228.269
• InChiKey: OYEYXPAVRUIWQI-UHFFFAOYSA-N

物化性质

• 沸点：
  409.9±28.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-甲基苯基)-2-氧代乙基甲烷磺酸酯 在 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到1-茚酮
  参考文献：
  名称：

  Photochemical Preparation of Highly Functionalized 1-Indanones

  摘要：

  A series of o-alkylphenyl alkyl ketones I were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-pi* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.

  DOI：

  10.1021/jo040173x
• 作为产物：
  描述：

  [羟基(甲烷磺酰氧基)碘代]苯 、 1-甲基苯基乙酮 以92%的产率得到2-(2-甲基苯基)-2-氧代乙基甲烷磺酸酯
  参考文献：
  名称：

  Photochemical Preparation of Highly Functionalized 1-Indanones

  摘要：

  A series of o-alkylphenyl alkyl ketones I were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-pi* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.

  DOI：

  10.1021/jo040173x

文献信息

• Straightforward and Highly Efficient Synthesis of α-Acetoxy Ketones through Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes
  作者：Weimin He、Jiannan Xiang、Chao Wu、Zhiwu Liang、Dong Yan

  DOI：10.1055/s-0033-1338513

  日期：——

  corresponding α-acetoxy ketones through gold-catalyzed intermolecular oxidation in the presence of 8-methylquinoline 1-oxide as the oxidant. The reaction probably proceeds through an α-oxo gold carbene intermolecular O–H insertion. A variety of terminal alkynes were efficiently converted into the corresponding α-acetoxy ketones through gold-catalyzed intermolecular oxidation in the presence of 8-methylquinoline

  摘要 在存在8-甲基喹啉1-氧化物作为氧化剂的情况下，通过金催化的分子间氧化将各种末端炔烃有效地转化为相应的α-乙酰氧基酮。该反应可能通过α-氧代金卡宾分子间OH插入而进行。 在存在8-甲基喹啉1-氧化物作为氧化剂的情况下，通过金催化的分子间氧化将各种末端炔烃有效地转化为相应的α-乙酰氧基酮。该反应可能通过α-氧代金卡宾分子间OH插入而进行。
• Photochemical Preparation of Highly Functionalized 1-Indanones
  作者：Pablo Wessig、Clemens Glombitza、Gunnar Müller、Janek Teubner

  DOI：10.1021/jo040173x

  日期：2004.10.1

  A series of o-alkylphenyl alkyl ketones I were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-pi* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.