2-(2-ethylphenyl)-2-oxoethyl methanesulfonate | 799804-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-ethylphenyl)-2-oxoethyl methanesulfonate
• 英文别名: [2-(2-Ethylphenyl)-2-oxoethyl] methanesulfonate
• CAS: 799804-35-6
• 化学式: C₁₁H₁₄O₄S
• 分子量: 242.296
• InChiKey: WOKVOXVNCBXFSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-ethylphenyl)-2-oxoethyl methanesulfonate 在 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到3-甲基-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：

  在 正丁基锂 、 氢氟酸 作用下， 以 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 2.0h， 生成 2-(2-ethylphenyl)-2-oxoethyl methanesulfonate
  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

• 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.