α-(o-ethylphenyl)acetophenone | 133145-62-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: α-(o-ethylphenyl)acetophenone
• 英文别名: 2-(2-Ethylphenyl)-1-phenylethanone
• CAS: 133145-62-7
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: LPMQBLPIVFLLJD-UHFFFAOYSA-N

物化性质

• 沸点：
  345.4±11.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-(o-ethylphenyl)acetophenone 以 氘代苯 为溶剂， 生成 (Z)-1-Methyl-2-phenyl-2-indanol 、 (E)-1-Methyl-2-phenyl-2-indanol
  参考文献：
  名称：

  High diastereoselectivity in the cyclization of 1,5-biradicals: what causes such sizeable steric barriers to biradical coupling?

  摘要：

  The high diastereoselectivities observed in the photocyclization of alpha-(o-ethylphenyl)acetophenones appear to reflect conformational equilibria in the triplet 1,5-biradical intermediates rather than steric barriers created during cyclization. The necessary biradical triplet-->singlet intersystem crossing is proposed to occur along the cyclization reaction coordinate since the orthogonality of the two singly-occupied p orbitals does not depress biradical lifetimes.

  DOI：

  10.1016/0040-4039(91)80844-v
• 作为产物：
  描述：

  2-乙基苯甲酸 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 乙醚 、 二甲基亚砜 、 苯 为溶剂， 反应 4.0h， 生成 α-(o-ethylphenyl)acetophenone
  参考文献：
  名称：

  Wagner, Peter J.; Meador, Michael A.; Zhou, Boli, Journal of the American Chemical Society, 1991, vol. 113, # 25, p. 9630 - 9639

  摘要：

  DOI：

文献信息

• Benzylic aroylation of toluenes with unactivated tertiary benzamides promoted by directed ortho-lithiation
  作者：Can-Can Bao、Yan-Long Luo、Hui-Zhen Du、Bing-Tao Guan

  DOI：10.1007/s11426-021-1035-5

  日期：2021.8

  amides and highly reactive organometallic reagents bring great challenges for an efficient and selective synthetic approach. Herein, we reported an lithium diisopropylamide (LDA)-promoted benzylic aroylation of toluenes with unactivated tertiary benzamides, providing a direct and efficient synthesis of various aryl benzyl ketones. This process features a kinetic deprotonative functionalization of toluenes

  甲苯的去质子官能化，由于酸性较弱，一般需要强碱，因此条件要求苛刻，会产生副产物。酰胺与有机金属试剂的直接亲核酰基取代反应可以为酮合成提供理想的解决方案。然而，惰性酰胺和高反应性有机金属试剂为高效和选择性的合成方法带来了巨大挑战。在此，我们报道了二异丙基酰胺锂 (LDA) 促进的甲苯与未活化的叔苯甲酰胺的苄基芳酰化，提供了各种芳基苄基酮的直接有效合成。该过程具有甲苯的动力学去质子官能化和易于获得的基础 LDA。机制研究表明，定向叔苯甲酰胺与 LDA 的邻位锂化促进了甲苯的苄基动力学去质子化，并引发了与酰胺的亲核酰基取代反应。
• H₂O₂-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water
  作者：Mengqiang Luo、Yaohong Zhang、Ping Fang、Yan Li、Chenze Qi、Yong Li、Runpu Shen、Kai Cheng、Hai Wang

  DOI：10.1039/d1ob02023d

  日期：——

  practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is

  已经发现了一种用于在水中室温合成 2-芳基苯乙酮的环境友好、经济高效且实用的方法。简便有效的转化涉及芳基肼与 α-芳基乙烯基叠氮化物在 H 2 O 2（作为自由基引发剂）和 PEG-800（作为相转移催化剂）存在下的氧化自由基加成。从绿色化学和有机合成的角度来看，本协议具有重要意义，因为它使用了廉价、无毒且易于获得的起始材料和试剂，并且易于进行克级合成，这为获取 2 提供了有吸引力的策略-芳基苯乙酮。
• Aqueous α-Arylation of Mono- and Diarylethanone Enolates at Low Catalyst Loading
  作者：Iratxe Astarloa、Raul SanMartin、María Teresa Herrero、Esther Domínguez

  DOI：10.1002/adsc.201701596

  日期：2018.4.17

  Acetophenone and deoxybenzoin derivatives are selectively α‐arylated using a combination of very small amounts of palladium acetate and diphenylphosphine oxide as catalyst system and water as the only solvent. Target di‐ and triarylethanones are isolated virtually free of metal residues, and the reaction is amenable to gram‐scale. A mechanistic proposal based on TEM images, poisoning experiments, kinetic

  苯乙酮和脱氧安息香衍生物通过使用极少量的乙酸钯和二苯膦氧化物作为催化剂体系，而水作为唯一溶剂，选择性地进行α-芳基化。分离出的目标二-和三芳基酮几乎不含金属残留物，反应量可达到克级。还提供了基于TEM图像，中毒实验，动力学图和ESI-MS光谱的机械方案。
• Asymmetric synthesis catalyst based on chiral brsnsted acid and method of asymmetric synthesis with the catalyst
  申请人：Akiyama Takahiko

  公开号：US20060276329A1

  公开（公告）日：2006-12-07

  A compound usable as an asymmetric synthesis catalyst which can be easily synthesized without using any metal such as a lanthanoid group element; a method of asymmetric synthesis with the compound; and a chiral compound obtained by the asymmetric synthesis method. A Broensted acid is used as a catalyst in asymmetric synthesis, the chiral Broensted acid being represented by formula (1) below or formula (3) below. The asymmetric synthesis method employs the catalyst. Asymmetric synthesis with the catalyst gives a chiral compound.

  一种可用作不使用任何类似于镧系元素的金属的不对称合成催化剂的化合物；使用该化合物进行不对称合成的方法；以及通过该不对称合成方法获得的手性化合物。在不对称合成中使用了一种布朗斯特酸作为催化剂，该手性布朗斯特酸由下式（1）或下式（3）表示。该不对称合成方法采用了该催化剂。使用该催化剂进行不对称合成可以得到手性化合物。
• Nickel-catalyzed cross-coupling of epoxides with aryltriflates: rapid and regioselective construction of aryl ketones
  作者：Jinglin Qu、Zijuan Yan、Xuchao Wang、Jun Deng、Feipeng Liu、Zi-Qiang Rong

  DOI：10.1039/d2cc02891c

  日期：——

  biologically active molecules and functional materials. Presented herein is a facile synthetic method for the construction of ketones via Ni-catalyzed cross coupling of epoxides with aryltriflates. A range of easily accessible epoxides can be highly regioselectively converted to the corresponding aryl ketones with good yields in a redox neutral fashion.

  芳基酮是一类最重要的有机化合物，广泛存在于各种药理化合物、生物活性分子和功能材料中。本文介绍了一种通过Ni 催化的环氧化物与芳基三氟甲磺酸酯的交叉偶联来构建酮的简便合成方法。一系列易于获得的环氧化物可以高度区域选择性地转化为相应的芳基酮，并以氧化还原中性方式以良好的收率。