(5-chloro-2-(pyridin-2-yl)phenyl)(phenyl)methanone | 1236046-60-8

• 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: (5-chloro-2-(pyridin-2-yl)phenyl)(phenyl)methanone
• 英文别名: (5-Chloro-2-pyridin-2-ylphenyl)-phenylmethanone；(5-chloro-2-pyridin-2-ylphenyl)-phenylmethanone
• CAS: 1236046-60-8
• 化学式: C₁₈H₁₂ClNO
• 分子量: 293.752
• InChiKey: RYPRIXKZJQBEHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯基乙炔 在 叔丁基过氧化氢 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (5-chloro-2-(pyridin-2-yl)phenyl)(phenyl)methanone
  参考文献：
  名称：

  Direct Carbo-Acylation Reactions of 2-Arylpyridines with α-Diketones via Pd-Catalyzed C–H Activation and Selective C(sp2)–C(sp2) Cleavage

  摘要：

  An efficient carbo-acylation reaction of 2-arylpyridines with alpha-diketones via Pd-catalyzed C-H bond activation and C-C bond cleavage in the presence of TBHP was developed that generated aryl ketones in good yields. The highly selective formation of aryl ketones was observed when 2-arylpyridines reacted with aromatic/aliphatic alpha-diketones.

  DOI：

  10.1021/ol3020557

文献信息

• Palladium-catalyzed decarboxylative, decarbonylative and dehydrogenative C(sp²)–H acylation at room temperature
  作者：Asik Hossian、Manash Kumar Manna、Kartic Manna、Ranjan Jana

  DOI：10.1039/c7ob01466j

  日期：——

  ambient temperature. A novel decarbonylative C–H acylation reaction has also been accomplished using aryl glyoxals as acyl surrogates. Finally, a practical C–H acylation via a dehydrogenative pathway has been demonstrated using commercially available benzaldehydes and aqueous hydroperoxides. We also disclose that acetonitrile solvent is optimal for the acylation reaction at room temperature and has a prominent

  在过去的几十年中，已经开发出了一系列令人印象深刻的C–H活化方法用于有机合成。但是，由于C–H键的固有惰性（例如，约110 kcal mol -1对于C（芳基）–H键的裂解，已经实现了苛刻的反应条件以克服高能跃迁状态，从而导致有限的底物范围和官能团耐受性。因此，迫切需要开发温和的C–H功能化方案，以在复杂分子框架的合成中充分利用C–H活化策略的全部潜力。尽管富电子的底物在相对温和的条件下会发生亲电金属化，但缺电子的底物会在强制条件下于高温下通过限速C–H插入来进行。此外，在钯催化中经常使用化学计量的有毒银盐来促进C–H活化过程，这从环境和工业角度来看都是不可接受的。我们在此报告Pd（II）在温和的条件下用α-酮羧酸催化2-芳基吡啶的脱羧C–H酰化。本方案不需要化学计量的银（I）盐作为添加剂，并且可以在环境温度下平稳地进行。使用芳基乙二醛作为酰基替代物也可以完成新型的脱羰CHH酰化反应。最后
• Decarboxylative acylation of arenes with mandelic acid derivatives via palladium-catalyzed oxidative sp² C–H activation
  作者：Xia Liu、Ze Yi、Jianhui Wang、Guiyan Liu

  DOI：10.1039/c4ra14107e

  日期：——

  An efficient palladium catalyzed decarboxylative acylation of arenes with mandelic acid derivatives via oxidative sp2 C–H activation in the presence of tert-butyl hydroperoxide has been developed. The acylation reaction is assisted by a pyridine directing group. The starting materials are inexpensive and readily available. This method provides an economical and convenient way to synthesize aryl ketones

  一种有效的钯催化与扁桃酸衍生物芳烃的酰化脱羧经由氧化SP 2 C-H活化的存在下叔丁基过氧化氢已被开发。酰化反应由吡啶引导基团辅助。起始原料便宜且容易获得。该方法提供了经济和方便的合成芳基酮的方法。
• Decarboxylative Acylation of Arenes with α-Oxocarboxylic Acids via Palladium-Catalyzed C−H Activation
  作者：Mingzong Li、Haibo Ge

  DOI：10.1021/ol1012857

  日期：2010.8.6

  An efficient palladium-catalyzed decarboxylative acylation of unactivated arenes with α-oxocarboxylic acids is reported. This method provides a novel access to aryl ketones.

  报道了未活化的芳烃与α-氧代羧酸的有效的钯催化的脱羧酰化。该方法为芳基酮提供了一种新颖的途径。
• Palladium catalyzed direct ortho C–H acylation of 2-arylpyridines using toluene derivatives as acylation reagents
  作者：Zhipeng Xu、Biao Xiang、Peipei Sun

  DOI：10.1039/c2ra22208f

  日期：——

  A facile ortho-acylation of 2-arylpyridines by a Pd-catalyzed oxidative C–H activation was developed, in which no prefunctionalized toluene derivatives were used as acylation reagents in a tandem reaction to form 2-pyridyldiaryl ketones with moderate yields.

  开发了一种简单的2-芳基吡啶的ortho-酰基化反应，采用Pd催化的氧化C–H活化，其中没有使用预功能化的甲苯衍生物作为酰基化试剂，通过级联反应形成2-吡啶基二芳基酮，产率适中。
• Nickel-catalyzed regioselective C–H acylation of chelating arenes: a new catalytic system for C–C bond formation <i>via</i> a radical process and its mechanistic explorations
  作者：Ze-lin Li、Peng-yu Wu、Kang-kang Sun、Chun Cai

  DOI：10.1039/c9nj02191d

  日期：——

  ortho C–H bond of chelating arenes via the Ni(II)-catalyzed cross dehydrogenative coupling strategy has been developed here. This new procedure exhibits excellent regioselectivity and good functional group tolerance. This discovery could be of great importance for the C–H acylation reactions of chelating arenes without any extraneous directing group and for the application of nickel-catalyzed C–H activation

  在前所未有的酰化邻螯合芳烃的C-H键通过在Ni（II）催化的交叉脱氢偶联策略已经这里开发。该新方法显示出极好的区域选择性和良好的官能团耐受性。这一发现对于不带任何外来直接基团的螯合芳烃的C–H酰化反应以及镍催化的C–H活化的应用可能具有重要意义。还描述了对反应过程的机械研究。