4-methyl-N-(4-methylphenyl)benzimidoyl chloride | 57575-88-9

• 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: 4-methyl-N-(4-methylphenyl)benzimidoyl chloride
• 英文别名: Benzenecarboximidoyl chloride, 4-methyl-N-(4-methylphenyl)-；4-methyl-N-(4-methylphenyl)benzenecarboximidoyl chloride
• CAS: 57575-88-9
• 化学式: C₁₅H₁₄ClN
• 分子量: 243.736
• InChiKey: JLCWNIZLQYVAEU-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56 °C(Solv: ligroine (8032-32-4))
• 沸点：
  160 °C(Press: 0.6 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 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：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(4-methylphenyl)benzimidoyl chloride 以 丙酮 为溶剂， 生成 1-methyl-3-[(4-tolyl)-(4-tolylimino)methyl]thiourea
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2,3,5-Substituted [1,2,4]Thiadiazoles as Allosteric Modulators of Adenosine Receptors

  摘要：

  A number of 2,3,5-substituted [1,2,4]thiadiazole analogues of SCH-202676 (N-(2,3-diphenyl-[1,2,4]thiadiazole-5(2H)-ylidene)methanamine, 7a) were synthesized and tested as potential allosteric modulators of adenosine receptors. All compounds were capable of displacing the binding of the radiolabeled agonist [H-3]CCPA to human A(1) adenosine receptors, whereas modest and varying effects were observed on the binding of [H-3]DPCPX, a radiolabeled antagonist for this receptor subtype. Four compounds, 7a (SCH-202676), 7k (LUF5792), 71 (LUF5794), and 8e (LUF5789), were selected for more detailed characterization. They all proved allosteric inhibitors of agonist binding, with 7k being most potent, whereas their effects on antagonist binding were more ambiguous. Subsequently, experiments were done on human adenosine A(2A) and A(3) receptors. Compounds 7a and 71 displayed peculiar displacement characteristics of both radiolabeled agonist and antagonist binding to A(2A) receptors, whereas 7a showed some activity on A(3) receptors.

  DOI：

  10.1021/jm030863d
• 作为产物：
  描述：

  乙烷,三氯氟- 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 4-methyl-N-(4-methylphenyl)benzimidoyl chloride
  参考文献：
  名称：

  由N，N'-二取代Am通过I 2 / KI介导的氧化性CC键的合成

  摘要：

  由C（sp 3）-H和C（sp 2）-H键形成的I 2 / KI促进的氧化C-C键形成反应已用于由N，N'-二取代的idine构建喹唑啉骨架。通过顺序的酰胺化，氯化和胺化反应，可以轻松地从相应的酰氯，苯胺和烷基/苄基胺制备所需的底物。在最佳的氧化环化条件下，所有这些s都可以方便地以中等到良好的产率转化为预期的产物。这种实用且对环境无害的方法适用于粗am中间体，也可以以克为单位进行。

  DOI：

  10.1021/acs.joc.6b02100

文献信息

• Amides as precursors of imidoyl radicals in cyclisation reactions
  作者：W. Russell Bowman、Anthony J. Fletcher、Jan M. Pedersen、Peter J. Lovell、Mark R.J. Elsegood、Elena Hernández López、Vickie McKee、Graeme B.S. Potts

  DOI：10.1016/j.tet.2006.10.030

  日期：2007.1

  Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals

  酰胺已成功地用作亚胺基自由基的前体，用于自由基环化。酰胺已通过与光气反应生成亚氨酰氯，然后与苯硒化钾反应，已转化为亚氨基酰硒化物。亚胺基硒化物与氢化三丁基锡（Bu 3 SnH）作为自由基介体反应，三乙基硼烷或AIBN作为引发剂，生成亚胺基自由基用于环化反应。酰亚胺基已被环化到烯烃上以产生2，3-取代的吲哚和-喹啉，并且还被吡咯和吲哚上以产生双环和三环杂芳烃。
• One-pot synthesis of polyfunctionalized quinolines <i>via</i> a copper-catalyzed tandem cyclization
  作者：Dianpeng Chen、Xuejun Sun、Yingying Shan、Jinmao You

  DOI：10.1039/c8ob02078g

  日期：——

  An efficient one-pot approach for the synthesis of polyfunctionalized quinolines was developed via a sequence of copper-catalyzed coupling reaction/propargyl-allenyl isomerization/aza-electrocyclization. Easily available starting materials, mild conditions, and a wide substrate scope make this approach potentially useful.

  通过一系列的铜催化偶联反应/炔丙基-烯基异构化/氮杂-电环化，开发了一种高效的一锅法合成多官能喹啉。容易获得的起始原料，温和的条件以及广泛的底物范围使该方法具有潜在的实用性。
• Palladium-Catalyzed Cyclocarbonylation of <i>o</i>-Iodoanilines with Imidoyl Chlorides to Produce Quinazolin-4(<i>3H</i>)-ones
  作者：Zhaoyan Zheng、Howard Alper

  DOI：10.1021/ol7029454

  日期：2008.3.1

  variety of substituted quinazolin-4(3H)-ones were prepared in 63-91% yields by the palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides and carbon monoxide. The reaction is believed to proceed via in situ formation of an amidine, followed by oxidative addition, CO insertion, and intramolecular cyclization to give the substituted quinazolin-4(3H)-ones.

  通过钯催化亚氨基酰氯和一氧化碳对碘代苯胺的环羰基化反应，可以制备63-91％产率的多种取代的喹唑啉-4（3H）-1。据信该反应通过via的原位形成，然后氧化加成，CO插入和分子内环化而进行，以给出取代的喹唑啉-4（3H）-。
• The Replacement of Electronegative Substituents by an Electron-transfer Mechanism. The Factors Governing the Reaction of Carbonyl and Imino Compounds with Organomagnesium Reagents
  作者：Masao Okubo、Yumiko Uematsu

  DOI：10.1246/bcsj.55.1121

  日期：1982.4

  In the reaction with ArN(MgBr)2, 1-halogenofluorenones afforded the normal condensation products, while 1-methoxyfluorenone gave the “condensation-replacement” product. On the basis of the characteristic product-distributions obtained in the two organomagnesium reactions, the mechanism of methoxy replacement was distinguished from that of halogen replacement. Factors governing the two reactions were

  为了研究电子转移引发的二芳基酮苯胺的邻甲氧基和邻卤代取代基被 ArMgBr 的芳基取代，制备了八个苯胺。然而，PhMgBr 的苯基所预期的邻甲氧基置换非常缓慢，并且没有发生邻氯置换。相比之下，1-取代（MeO，Br，Cl）芴酮的苯胺产生了替代产物：在卤代苯胺的情况下，通过自由基途径形成的副产物的分布与甲氧基苯胺的情况明显不同。阿尼尔。在与 ArN(MgBr)2 的反应中，1-卤代芴酮得到正常的缩合产物，而 1-甲氧基芴酮得到“缩合-置换”产物。根据在两个有机镁反应中获得的特征产物分布，甲氧基取代的机制与卤素取代的机制不同。提出并讨论了控制这两种反应的因素：结构...
• Fluorescent benzene-centered mono-, bis- and tris-triazapentadiene–boron complexes
  作者：Christoph Glotzbach、Nadine Gödeke、Roland Fröhlich、Constantin-Gabriel Daniliuc、Shohei Saito、Shigehiro Yamaguchi、Ernst-Ulrich Würthwein

  DOI：10.1039/c5dt00908a

  日期：——

  A series of novel benzene centered mono-, bis- and tris-1,3,5-triazapentadiene ligands 6a–e was synthesized and investigated with respect to their reactivity towards triphenylborane. The resulting blue-fluorescent boron complexes 14a–e with a six-membered ring chelate structure show excellent thermal and chemical stability. All title compounds were completely characterized including X-ray diffraction

  合成了一系列新颖的以苯为中心的单，双和三，1,3,5-三氮杂戊二烯配体6a-e，并研究了它们对三苯基硼烷的反应性。所得的具有六元环螯合物结构的蓝色荧光硼配合物14a-e显示出出色的热稳定性和化学稳定性。所有标题化合物均已完全鉴定，包括14a–c和14e的X射线衍射研究。尽管所有三类化合物的吸收光谱相似，但荧光光谱显示出明显的差异。因此，14a，b的发射光谱显示斯托克斯位移为4100–6700 cm -1在溶液和固态中均具有较低的量子产率。但是，与14a，b相比，体积更大的化合物14c–e显示出更大的摩尔消光系数和较小的红移。对于所有化合物，与二氯甲烷溶液相比，我们观察到固态的红移荧光明显更强。为了解释吸收特性，基于DFT几何优化进行了TD-DFT研究。