2-hydroxy-2-methyl-1-(2-methylphenyl)-1-propanone | 15482-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-2-methyl-1-(2-methylphenyl)-1-propanone
• 英文别名: 1-o-Tolyl-2-hydroxy-2-methylpropanon-(1)；2-Hydroxy-2-methyl-1-(2-methylphenyl)propan-1-one
• CAS: 15482-19-6
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: WOSSHYZFXAMNCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-methyl-1-(2-methylphenyl)-1-propanone 在 aluminum tri-tert-butoxide 作用下， 以 甲苯 为溶剂， 生成 2-Hydroxy-2-o-tolyl-butanon-(3)
  参考文献：
  名称：

  Elphimoff-Felkin,I.; Verrier,M., Bulletin de la Societe Chimique de France, 1967, p. 1052 - 1057

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基苯甲醛 在 正丁基锂 、 Montmorillonite-K 10 、 二异丙胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 78.75h， 生成 2-hydroxy-2-methyl-1-(2-methylphenyl)-1-propanone
  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

• Photopolymerizable coating products
  申请人：OECE Industrie Chimiche Spa

  公开号：EP0402932A1

  公开（公告）日：1990-12-19

  The invention relates to both highly pigmented and transparent coating products which can be polymerized photochemically by irradiation with emission in the near ultraviolet and in the visible, possibly followed by additional irradiation in she infrared and/or in the ultraviolet, and consist of homogeneous dispersions of ethylenically unsaturated polymer substances, and photocatalysts based on compounds of metals of group IV A and of groups I B to VII B and VIII of the periodic table, preferably in the presence of photoinitiators chosen from derivatives of thioxanthone, acetophenone, benzophenone, benzoin, ketoxime and acylphosphine oxide, and either containing or not containing pigments and/or fillers.

  本发明涉及高颜料和透明涂料产品，这些产品可通过近紫外线和可见光辐照进行光化 学聚合，可能还需要红外线和/或紫外线辐照，由乙烯不饱和聚合物物质的均匀分散体组 成、以及基于元素周期表中第 IV A 族和第 I B 至 VII B 和 VIII 族金属化合物的光催化剂，最好是在光引发剂的存在下，光引发剂选自硫杂蒽酮、苯乙酮、二苯甲酮、安息香、酮肟和酰基氧化膦的衍生物，以及含有或不含有颜料和/或填料。
• Elphimoff-Felkin,I.; Verrier,M., Bulletin de la Societe Chimique de France, 1967, p. 1047 - 1052
  作者：Elphimoff-Felkin,I.、Verrier,M.

  DOI：——

  日期：——
• 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.
• Elphimoff-Felkin,I.; Verrier,M., Bulletin de la Societe Chimique de France, 1967, p. 1052 - 1057
  作者：Elphimoff-Felkin,I.、Verrier,M.

  DOI：——

  日期：——