2,3'-Dimethyl-benzophenon | 22682-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3'-Dimethyl-benzophenon
• 英文别名: 2,3'-dimethylbenzophenone；m-tolyl(o-tolyl)methanone；(2-Methylphenyl)(3-methylphenyl)methanone；(2-methylphenyl)-(3-methylphenyl)methanone
• CAS: 22682-29-7
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: KWSGMNYAGVBFIB-UHFFFAOYSA-N

物化性质

• 熔点：
  -18 °C
• 沸点：
  125-127 °C0.3 mm Hg(lit.)
• 密度：
  1.083 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 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：

  2,3'-Dimethyl-benzophenon 在 吡啶 、 sodium hydroxide 、 potassium permanganate 、 硫酸 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 3-[3-(2-Imidazol-1-ylethyl)-4-oxophthalazin-1-yl]benzoic acid
  参考文献：
  名称：

  Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones

  摘要：

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.

  DOI：

  10.1021/jm00077a008
• 作为产物：
  描述：

  间甲基苯腈 在 盐酸 作用下， 生成 2,3'-Dimethyl-benzophenon
  参考文献：
  名称：

  Ketimines. II. Diaryl Type¹

  摘要：

  DOI：

  10.1021/ja01167a053

文献信息

• Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes
  作者：Jianhui Chen、Chenhui Chen、Chonglei Ji、Zhan Lu

  DOI：10.1021/acs.orglett.6b00453

  日期：2016.4.1

  Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine–cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral

  通过使用稳定的手性恶唑啉亚氨基吡啶-钴络合物作为前催化剂，开发了对映体选择性高的钴催化的1,1-二芳烃的氢化反应。观察到独特的邻氯化物效应实现了高对映选择性。易于除去以及氯基团的进一步转化使该方案成为合成各种手性1,1-二芳基乙烷的潜在有用替代品。此过程可以在室温下1克大气压的氢气中以克为单位成功进行。
• Transition-metal-free carbonylation of aryl halides with arylboronic acids by utilizing stoichiometric CHCl₃ as the carbon monoxide-precursor
  作者：Fangning Xu、Dan Li、Wei Han

  DOI：10.1039/c9gc00598f

  日期：——

  Under transition-metal-free conditions, carbonylative Suzuki couplings of aryl halides with arylboronic acid using stoichiometric CHCl3 as the carbonyl source has been developed. The simple, efficient, and environmentally benign method was successfully applied to the synthesis of Fenofibric acid, naphthyl phenstatin, and carbon-13 labeled biaryl ketone.

  在无过渡金属的条件下，已开发出使用化学计量的CHCl 3作为羰基源的芳基卤化物与芳基硼酸的羰基Suzuki偶联反应。简单，高效，环境友好的方法已成功地用于合成非诺贝酸，萘酚他汀和碳13标记的联芳基酮。
• Redox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis
  作者：Renhe Li、Feipeng Liu、Guangbin Dong

  DOI：10.1016/j.chempr.2019.02.005

  日期：2019.4

  cooperative catalysis, also known as the Catellani reaction, has become an increasingly useful method for site-selective arene functionalization; however, certain constraints still exist because of its intrinsic mechanistic pathway. Herein, we report a redox-neutral ortho functionalization of aryl boroxines via Pd/NBE catalysis. An electrophile, such as carboxylic acid anhydrides or O-benzoyl hydroxylamines,

  钯/降冰片烯（Pd / NBE）协同催化，也称为Catellani反应，已成为位点选择性芳烃官能化的一种越来越有用的方法。但是，由于其固有的机理途径，仍然存在某些限制。在这里，我们报告通过Pd / NBE催化的芳基硼氧烷的氧化还原中性邻位官能化。亲电子试剂，例如羧酸酐或O-苯甲酰基羟胺，在环硼氧烷邻位偶联，质子作为第二种亲电子试剂引入ipso位置。该反应不需要额外的氧化剂或还原剂，并且避免了化学计量的碱或酸，从而可以耐受各种官能团。特别地，证明了芳基碘和环硼氧烷部分之间的正交化学选择性，其可用于控制反应序列。最后，氘标记研究支持ipso质子化途径。这种独特的机械特性可能会激发新型Pd / NBE催化的转化的发展。
• Palladium−Phosphinous Acid-Catalyzed Cross-Coupling of Aryl and Acyl Halides with Aryl-, Alkyl-, and Vinylzinc Reagents
  作者：Hanhui Xu、Kekeli Ekoue-Kovi、Christian Wolf

  DOI：10.1021/jo801445y

  日期：2008.10.3

  biaryls in up to 92% yield. Aryl halides also undergo POPd7-catalyzed aryl-vinyl and aryl-alkyl bond formation under mild conditions. Styrenes and alkylarenes were prepared in 79-93% yield from aryl halides and vinyl or alkylzinc reagents. The replacement of aryl halides by acyl halides provides access to ketones which were produced in up to 98% yield when POPd was used as catalyst. This approach overcomes

  已经制备了几种钯次膦酸，并将其用于芳基或酰基卤与脂族和芳族有机锌试剂的交叉偶联反应。发现POPd7催化的芳基卤化物（包括富含电子的芳基氯化物）和芳基锌试剂的反应可提供具有烷氧基，烷硫基，氨基，酮，氰基，硝基，酯基和杂芳基基团的联芳基，产率为75-93％。使用位阻受阻的底物可获得优异的结果，该底物以高达92％的收率得到二和三邻位取代的联芳基。在温和条件下，芳基卤化物也经历POPd7催化的芳基-乙烯基和芳基-烷基键的形成。由芳基卤化物和乙烯基或烷基锌试剂制备苯乙烯和烷基芳烃的产率为79-93％。用酰基卤取代芳基卤化物可得到酮，当使用POPd作为催化剂时，酮的产率可高达98％。该方法克服了传统的Friedel-Crafts酰化方法的受限底物范围，降低的区域控制和较低的官能团耐受性。
• Synthesis of Substituted Phenyl Ketones via Pd-Catalysed hydrodechlorination of Their Polychlorinated Derivatives
  作者：Andrea Bomben、Carlos A. Marques、Maurizio Selva、Pietro Tundo

  DOI：10.1055/s-1996-4344

  日期：1996.9

  The following compounds, 2- and 3-methylacetophenones, 2- and 3-methylbenzophenones, and 2,2’-, 2,3’- and 3,3’-dimethylbenzophenones have been synthesized through a Pd-catalysed hydrodechlorination of the corresponding dichlorinated derivatives. The reaction has been carried out under multiphase conditions at 30-50°C, by bubbling H2 at atmospheric pressure into a biphasic system constituted by an organic substrate solution (isooctane solvent) and an aqueous alkaline solution (50% aq KOH), in the presence of Pd/C (5% wt) and Aliquat 336 (triaprylylmethylammonium chloride). Likewise, fluorinated aceto- and benzophenones (4-fluoro-3-methylacetophenone and 4-fluoro-3-methylbenzo-, 4-fluoro-2’,3-dimethylbenzo-, 4-fluoro-3,3’-dimethylbenzophenones) have been prepared starting from the corresponding chlorinated methylfluoro- and dimethylfluoro ketones. Under such conditions, the presence of the onium salt allows the reaction to proceed with a high chemoselectivity: chlorine is removed while both the reduction of the carbonyl group and/or fluorine removal are prevented.

  通过钯催化的相应二氯化合物的氢脱氯反应，合成了以下化合物：2-和3-甲基乙酰苯酮、2-和3-甲基苯甲酮，以及2,2’-、2,3’-和3,3’-二甲基苯甲酮。反应在30-50°C的多相条件下进行，通过将氢气在常压下鼓泡通入由有机底物溶液（异辛烷溶剂）和水性碱性溶液（50% aq KOH）组成的双相系统中，在Pd/C（5% wt）和Aliquat 336（三吡啶基甲基氯化铵）的存在下进行。同样，氟化乙酰苯酮和苯甲酮（4-氟-3-甲基乙酰苯酮和4-氟-3-甲基苯甲酮、4-氟-2’,3-二甲基苯甲酮、4-氟-3,3’-二甲基苯甲酮）从相应的氯化甲基氟和二甲基氟酮出发制备。在这些条件下，季铵盐的存在使得反应具有高度的化学选择性：氯被移除，同时羰基的还原和/或氟的去除被阻止。