2-methyl-N-(4-methylphenylmethyl)-benzamide | 194654-68-7

• 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-methyl-N-(4-methylphenylmethyl)-benzamide
• 英文别名: 2-methyl-benzoic acid-(4-methyl-benzylamide)；N-(4-Methyl-benzyl)-o-toluamid；2-Methyl-benzoesaeure-(4-methyl-benzylamid)；2-methyl-N-(4-methylbenzyl)benzamide；2-methyl-N-[(4-methylphenyl)methyl]benzamide
• CAS: 194654-68-7
• 化学式: C₁₆H₁₇NO
• mdl: MFCD01213457
• 分子量: 239.317
• InChiKey: UIQJURGJJYRAHM-UHFFFAOYSA-N

物化性质

• 沸点：
  417.9±34.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-N-(4-methylphenylmethyl)-benzamide 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 3-(4-Chloro-phenyl)-2-(4-methyl-benzyl)-2H-isoquinolin-1-one
  参考文献：
  名称：

  从二锂化 2-甲基-N-芳基苯甲酰胺、2-甲基-N-(芳甲基)-苯甲酰胺或2-甲基苯甲酸、2,2-二甲基酰肼制备取代的1(2H)-异喹啉酮

  摘要：

  摘要 2-甲基-N-芳基苯甲酰胺（N-芳基-邻-甲苯甲酰胺），2-甲基-N-（芳甲基）-苯甲酰胺（取代苄基，N-苄基-邻-甲苯甲酰胺），或2-甲基苯甲酸，2， 2-二甲基酰肼（邻甲苯甲酸，N，N-二甲基酰肼）用过量的二异丙基氨基锂二锂化，所得聚阴离子型中间体与芳族酯缩合，然后酸环化为3-取代-1（2H）-异喹啉酮（异喹啉）。

  DOI：

  10.1080/00397919708005002
• 作为产物：
  描述：

  邻甲基苯甲酰氯 、 4-甲基苄胺 以94%的产率得到2-methyl-N-(4-methylphenylmethyl)-benzamide
  参考文献：
  名称：

  从二锂化 2-甲基-N-芳基苯甲酰胺、2-甲基-N-(芳甲基)-苯甲酰胺或2-甲基苯甲酸、2,2-二甲基酰肼制备取代的1(2H)-异喹啉酮

  摘要：

  摘要 2-甲基-N-芳基苯甲酰胺（N-芳基-邻-甲苯甲酰胺），2-甲基-N-（芳甲基）-苯甲酰胺（取代苄基，N-苄基-邻-甲苯甲酰胺），或2-甲基苯甲酸，2， 2-二甲基酰肼（邻甲苯甲酸，N，N-二甲基酰肼）用过量的二异丙基氨基锂二锂化，所得聚阴离子型中间体与芳族酯缩合，然后酸环化为3-取代-1（2H）-异喹啉酮（异喹啉）。

  DOI：

  10.1080/00397919708005002

文献信息

• [EN] ISOQUINOLINONE DERIVATIVES AND THEIR USE AS THERAPEUTIC AGENTS<br/>[FR] DERIVES D'ISOQUINOLINONE ET LEUR UTILISATION COMME AGENTS THERAPEUTIQUES
  申请人：X CEPTOR THERAPEUTICS INC

  公开号：WO2004058717A1

  公开（公告）日：2004-07-15

  This invention is directed to isoquinolinone derivatives and their use in modulating the activity of orphan nuclear receptors, pharmaceutical compositions containing such derivatives, and methods of using such derivatives in treating disease-states associated with nuclear receptor activity.

  这项发明涉及异喹啉酮衍生物及其在调节孤儿核受体活性中的应用，包含这种衍生物的药物组合物，以及使用这种衍生物治疗与核受体活性相关的疾病状态的方法。
• On the Catalytic Action of Japanese Acid Earth. XI. The Isomerisation of Aldehydes to Ketones and the Explanation of the Migration of the Radicals from the Standpoint of the Electronic Theory (<i>Continued and concluded</i>)
  作者：Koshiro Ishimura

  DOI：10.1246/bcsj.16.293

  日期：1941.9

  (1) All the phenomena hitherto ascribed to the characteristic catalytic action of Japanese acid earth can be explained by taking its strong electron-seeking property into consideration. Thus its ability to promote the hydrolysis of cane sugar or starch and the oxidation of pyrogallol and its property to give various oxidase-like colour reactions are all due to its selective adsorptive power for hydroxyl ion. The facts can similarly be explained that the dehydration or deamination of various organic compounds takes place through its catalytic action followed by the intramolecular rearrangement, as observed in the reaction of producing cyclopentane derivatives from cyclohexanol, cyclohexylamine or their methyl derivatives.The initial step of the formation of β,β′-dinaphthyl from naphthalene in the presence of the earth is the polarisation of the naphthalene molecule promoted by its electron-seeking property.(2) Several diarylacetaldehydes have been newly synthesised and found to rearrange themselves to give the corresponding ketones, when heated at 300°C. in the presence of the earth. Thus phenyl p-tolyl and m-tolyl p-tolyl acetaldehydes gave phenyl p-methylbenzyl and m-tolyl p-methylbenzyl ketones respectively, while o-tolyl p-tolyl and p-tolyl p-chlorophenyl acetaldehydes gave the respective mixtures of o-toly p-methylbenzyl and p-tolyl o-methylbenzyl ketones and of p-chlorophenyl p-methylbenzyl and p-tolyl p-chlorobenzyl ketones.(3) By comparing the yields in the isomeric ketones thus produced the order of the facility of separation of the different aryl groups was determined as follows:—Phenyl, m-tolyl>p-chlorophenyl>o-tolyl>p-tolyl.The phenyl group may most probably have the greater migratory tendency than the m-tolyl.(4) The mechanism of the conversion of the aldehydes to the ketones has been discussed. It has been postulated that an electromeric displacement of electrons in the carbonyl group (Remark: Graphics omitted.) is promoted by the action of the earth, and one of the aryl groups migrates with its valency electrons from the adjacent a-carbon atom to the depleted carbonyl carbon. A proton is then splitted from the carbonyl carbon and unites with the carbonyl oxygen to give the enolic form of the ketone, isomeric to the aldehyde. The conclusion has been reached that the more electron-attracting of the two aryl groups must be first separated as anion.(5) It was confirmed that the capacity of the p-tolyl group for electron-release is much larger than those of o-tolyl, m-tolyl, phenyl and p-chlorophenyl groups. By these results a new chemical evidence has been given for the tautomeric effect of the methyl group.(6) Following compounds have been newly synthesised and their constitutions were confirmed:— a-phenyl a-p-tolyl, a-m-tolyl a-p-tolyl, a-o-tolyl a-p-tolyl and a-p-chlorophenyl a-p-tolyl ethylene glycols and their benzoyl derivatives; p-tolyl m-methylbenzyl, m-tolyl p-methylbenzyl, o-tolyl p-methylbenzyl, p-tolyl o-methylbenzyl, p-chlorophenyl p-methyl-benzyl and p-tolyl p-chlorobenzyl ketones and their oximes and semi-carbazones; m-tolyl p-tolyl, o-tolyl p-tolyl and p-tolyl p-chlorophenyl acetic acids; p-methylbenzoyl carbinol, p-chlorobenzoyl methyl acetate and p-chlorobenzoyl carbinol.(7) o-Tolyl p-methylbenzyl and m-tolyl p-methylbenzyl ketones have been found to be oxidised slowly by the action of atmospheric oxygen on long standing, giving the mixtures of o-toluic and p

  (1) 考虑到日本酸土的强电子寻找特性，迄今为止所有归因于其催化作用特征的现象都可以得到解释。因此，日本酸土能够促进蔗糖或淀粉的水解、焦酚的氧化以及产生各种类似氧化酶的颜色反应，都是由于它对羟基离子具有选择性吸附力。同样，在环己醇、环己胺或其甲基衍生物生成环戊烷衍生物的反应中也可以看到，各种有机化合物的脱水或脱氨基反应是在其催化作用下进行的，随后发生分子内重排。(2)新合成了几种二芳基乙醛，并发现它们在有土的情况下于 300°C 加热时会重新排列，生成相应的酮。因此，苯基对甲苯基和间甲苯基对甲苯基乙醛分别生成苯基对甲基苄基和间甲苯基对甲基苄基酮，而邻甲苯基对甲苯基和对甲苯基对氯苯基乙醛分别生成邻甲苯基对甲基苄基和对甲苯基邻甲基苄基酮的混合物，以及对氯苯基对甲基苄基和对甲苯基对氯苄基酮的混合物。(3) 通过比较由此生成的异构酮的产率，确定了不同芳基的分离便利性顺序如下：苯基、间甲苯基>对氯苯基>邻甲苯基>对甲苯基。据推测，在地球的作用下，羰基（注：图形省略）中的电子发生了电迁移，其中一个芳基带着其价电子从相邻的 a 碳原子迁移到耗尽的羰基碳上。然后，一个质子从羰基碳上分离出来，与羰基氧结合，得到酮的烯醇形式，与醛同分异构。(5)经证实，对甲苯基释放电子的能力远远大于邻甲苯基、间甲苯基、苯基和对氯苯基。这些结果为甲基的同分异构效应提供了新的化学证据。(6) 新合成了下列化合物，并确认了它们的组成：- a-苯基 a-对甲苯基、a-间甲苯基 a-对甲苯基、a-邻甲苯基 a-对甲苯基和 a-对氯苯基 a-对甲苯基乙二醇及其苯甲酰衍生物；对甲苯基间甲基苄基、间甲苯基对甲基苄基、邻甲苯基对甲基苄基、对甲苯基邻甲基苄基、对氯苯基对甲基苄基和对甲苯基对氯苄基酮及其肟和半咔唑酮；间甲苯基对甲苯、邻甲苯基对甲苯和对甲苯基对氯苯乙酸；对甲基苯甲酰基甲 醛、对氯苯甲酰甲基乙酸酯和对氯苯甲酰甲醇。(7) 研究发现，邻甲苯基对甲基苄基和间甲苯基对甲基苄基酮在大气中的氧气作用下，长期存 在会被缓慢氧化，生成邻甲苯基和间甲苯基对甲基苄基酮的混合物。
• Isoquinolinone derivatives and their use as therapeutic agents
  申请人：X-Ceptor Therapeutics Inc.

  公开号：US20040204447A1

  公开（公告）日：2004-10-14

  Compounds of formula (I): 1 wherein n, R 1 , R 2 , R 3 and R 7 are disclosed herein, are useful in treating disease-states associated with nuclear receptor activity. Pharmaceutical compositions comprising and methods of using said compounds are also disclosed herein.

  式(I)的化合物：其中n，R1，R2，R3和R7如下所示，可用于治疗与核受体活性相关的疾病状态。本文还披露了包含该化合物的制药组合物和使用该化合物的方法。
• Isoquinolinone Derivatives and Their Use As Therapeutic Agents
  申请人：Johnson Alan T.

  公开号：US20080132521A1

  公开（公告）日：2008-06-05

  Compounds of formula (I): wherein n, R 1 , R 2 , R 3 and R 7 are disclosed herein, are useful in treating disease-states associated with nuclear receptor activity. Pharmaceutical compositions comprising and methods of using said compounds are also disclosed herein.

  公式（I）的化合物：其中n，R1，R2，R3和R7在此披露，可用于治疗与核受体活性相关的疾病状态。本文还披露了包含该化合物的制药组合物以及使用该化合物的方法。
• TRIAZOLOPYRIDINES
  申请人：Schulze Volker

  公开号：US20140120087A1

  公开（公告）日：2014-05-01

  The present invention relates to triazolopyridine compounds of general formula (I): in which R 1 , R 2 , R 3 , R 4 , and R 5 are as given in the description and in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

  本发明涉及通式（I）的三唑吡啶化合物，其中R1、R2、R3、R4和R5如描述和权利要求中所给出，以制备所述化合物的方法，包括包含所述化合物的药物组合物和组合物，以及用于制造用于治疗或预防疾病的药物组合物的所述化合物的用途，以及用于制备所述化合物的中间体化合物。