1-(2-甲基苯基)-2-苯乙酮 | 16216-13-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(2-甲基苯基)-2-苯乙酮
• 英文名称: 2-phenyl-1-o-tolylethanone
• 英文别名: 2-phenyl-1-(o-tolyl)ethan-1-one；1-(2-methylphenyl)-2-phenylethanone；Benzyl-o-tolyl-keton；2'-Methyl-2-phenylacetophenone
• CAS: 16216-13-0
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: XZHWEJVJMHRXPP-UHFFFAOYSA-N

物化性质

• 沸点：
  318-320 °C
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914399090

反应信息

• 作为反应物：
  描述：

  1-(2-甲基苯基)-2-苯乙酮 在 N-甲基咪唑 作用下， 以 甲醇 为溶剂， 生成 2-苯基-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：

  2-hydroxy-2'-methylacetophenone 在 二氯化双(三环己基膦)镍(II) 、 三乙胺 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.67h， 生成 1-(2-甲基苯基)-2-苯乙酮
  参考文献：
  名称：

  Arylation of α-pivaloxyl ketones with arylboronic reagents via Ni-catalyzed sp3 C–O activation

  摘要：

  开发了一种通过镍催化的sp3 C–O活化将α-皮伐氧基酮与α-芳基酮进行Suzuki–Miyaura耦合的方法。本研究提供了一种便利的方法，以便从易得的α-羟基羰基化合物构建α-芳基化产物。

  DOI：

  10.1039/c1cc11193k

文献信息

• Copper-Catalyzed Oxidation of Deoxybenzoins to Benzils under Aerobic Conditions
  作者：Antonella Goggiamani、Sandro Cacchi、Giancarlo Fabrizi、Antonia Iazzetti、Rosanna Verdiglione

  DOI：10.1055/s-0033-1338451

  日期：——

  Abstract A novel copper-catalyzed approach to benzils from readily available deoxybenzoins under neutral conditions using air as the oxidant has been developed. The reaction tolerates a variety of useful substituents including chloro, bromo, iodo, keto, ester, and cyano groups. A novel copper-catalyzed approach to benzils from readily available deoxybenzoins under neutral conditions using air as the

  摘要 已经开发出一种新颖的铜催化方法，该方法是在中性条件下使用空气作为氧化剂，从容易获得的脱氧安息香素制取苯甲醚。该反应可耐受多种有用的取代基，包括氯，溴，碘，酮，酯和氰基。 已经开发出一种新颖的铜催化方法，该方法是在中性条件下使用空气作为氧化剂，从容易获得的脱氧安息香素制取苯甲醚。该反应可耐受多种有用的取代基，包括氯，溴，碘，酮，酯和氰基。
• Catalytic Efficient Nazarov Reaction of Unactivated Aryl Vinyl Ketones via a Bidentate Diiron Lewis Acid Activation Strategy
  作者：Xin Zhou、Yukun Zhao、Yang Cao、Lirong He

  DOI：10.1002/adsc.201700820

  日期：2017.10.4

  has been accomplished by employing aryl boric acid/Fe(OTf)3. Significant progress was obtained in utilizing an extremely broad substrate scope, giving indanones in high yields with high regioselectivities and diastereoselectivities. The mechanistic investigation supports a bidentate diiron Lewis acid catalysis, and the strong double electrophilic activation of aryl vinyl ketones via simultaneous coordination

  通过使用芳基硼酸/ Fe（OTf）3可以完成未活化的芳基乙烯基酮的高效催化Nazarov反应。在利用极其广泛的底物范围方面获得了重大进展，从而以高产率获得了茚满酮，并具有较高的区域选择性和非对映选择性。机理研究支持双齿二铁路易斯酸的催化，芳基乙烯基酮通过同时配位的强双亲电活化在实现高反应效率方面起着关键作用。
• Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones
  作者：Dina Moustafa、Chelsea Sweet、Hyun Lim、Brenda Calalpa、Parminder Kaur

  DOI：10.1016/j.tetlet.2018.09.021

  日期：2018.10

  A direct and efficient synthesis of arylketones via arylboronic acid addition to nitriles in presence of inexpensive Mn/Cu catalytic system is reported. The use of non-precious Mn and Cu salts has been found to be highly advantageous both in terms of accessibility as well as cost effectiveness. A series of arylboronic acids as well as nitriles were used to synthesize a variety of symmetrical and unsymmetrical

  据报道，在廉价的Mn / Cu催化体系存在下，通过将芳基硼酸加成腈直接有效地合成芳基酮。已经发现，就可及性和成本效率而言，使用非贵重的Mn和Cu盐是非常有利的。一系列芳基硼酸和腈用于合成各种对称和不对称的芳基酮。基于文献研究，预期该反应机理将通过芳基自由基中间体，该中间体与亚铜中间体腈水解后与铜活化的腈反应以得到所需的芳基酮。
• A Remarkably Simple Hybrid Surfactant-NHC Ligand, Its Gold-Complex, and Application in Micellar Catalysis
  作者：Andreas Rühling、Hans-Joachim Galla、Frank Glorius

  DOI：10.1002/chem.201502542

  日期：2015.8.24

  A combination of an N‐heterocyclic carbene (NHC) ligand and a structurally simple surfactant has been realized, the hybrid surfactant–NHC. The related gold complex was synthesized, fully characterized, and applied in catalysis. This remarkably simple strategy allows, in combination with a co‐surfactant, the application of gold catalysis in water.

  N-杂环卡宾（NHC）配体和结构简单的表面活性剂（杂化表面活性剂–NHC）的组合已经实现。合成了相关的金络合物，对其进行了充分表征，并将其用于催化。这种非常简单的策略允许与助表面活性剂一起在水中应用金催化。
• Role of water in intrazeolite photochemistry
  作者：Z. Zhang、N.J. Turro、L. Johnston、V. Ramamurthy

  DOI：10.1016/0040-4039(96)00971-9

  日期：1996.7

  The photochemical and photophysical behavior of several ketones included within Na X zeolites is dependent upon the adsorbed water within the zeolite. Results suggest that when the zeolite is dry (water free), the guest ketones reside within supercages and when the internal structure is filled with water the guest molecules are displaced to the external surface.

  Na X沸石中包含的几种酮的光化学和光物理行为取决于沸石中吸附的水。结果表明，当沸石干燥（无水）时，客体酮保留在超笼中；当内部结构充满水时，客体分子被置换到外表面。