4-methyl-N-(naphthalen-1-yl)benzamide | 79630-21-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methyl-N-(naphthalen-1-yl)benzamide
• 英文别名: Benzamide, N-(1-naphthyl)-4-methyl-；4-methyl-N-naphthalen-1-ylbenzamide
• CAS: 79630-21-0
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: URUKLNMVYAVDAS-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.8 [ug/mL]
• 保留指数：
  2630

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-methyl-N-(naphthalen-1-yl)benzamide 在 劳森试剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.33h， 生成 2-(p-tolyl)naphtho[1,2-d]thiazole
  参考文献：
  名称：

  Synthesis of 2-Arylbenzothiazoles by DDQ-Promoted Cyclization of Thioformanilides; A Solution-Phase Strategy for Library Synthesis

  摘要：

  数种取代苯并噻唑通过分子内环化，在高产率下合成，以硫代酰胺与2,6-二氯-3,5-二氰基-1,4-苯醌（DDQ）在二氯甲烷中室温反应。所得到的2-芳基苯并噻唑可通过用强碱性离子交换树脂处理反应混合物，从还原型DDQ副产物（4,5-二氯-3,6-二羟基邻苯二腈）中分离出来。本方法在苯并噻唑环或2-芳基部分上引入官能团具有高度的灵活性，进而为平行合成提供了骨架。

  DOI：

  10.1055/s-2007-965929
• 作为产物：
  描述：

  3,5-Dinitro-N-o-tolyl-thiobenzamide 反应 0.1h， 以92%的产率得到4-methyl-N-(naphthalen-1-yl)benzamide
  参考文献：
  名称：

  A Mild and Convenient Method for Conversion of Thioamides to Their Corresponding Amides Using Acidified Wet Silica-Supported Permanganate Under Solvent-Free Conditions

  摘要：

  A mild and efficient method for conversion of thioamides to their corresponding amides is reported. A series of thioamides are transformed to their corresponding carbonyl compounds in good to excellent yields by acidified wet silica-supported permanganate under solid phase conditions.

  DOI：

  10.1080/10426500802080865

文献信息

• Intramolecular charge transfer with N-benzoylaminonaphthalenes. 1-Aminonaphthalene versus 2-aminonaphthalene as electron donors
  作者：Xuan Zhang、Chun-Hua Liu、Li-Hong Liu、Fang-Ying Wu、Lin Guo、Xiang-Ying Sun、Chao-Jie Wang、Yun-Bao Jiang

  DOI：10.1039/b210106h

  日期：2003.2.11

  derivatives in cyclohexane and was assigned to the CT state by the observation of a substantial red shift with increasing solvent polarity or with increasing electron-withdrawing ability of the substituent. The CT emission energies were found to follow a linear relationship with the Hammett constant of the substituent and the value of the linear slope for 1-NBAs (-0.45 eV) was higher than that of 2-NBAs (-0

  制备了在苯甲酰基苯环的对位或间位具有不同取代基的N-（取代-苯甲酰基）-1-氨基萘和N-（取代-苯甲酰基）-2-氨基萘（1-NBA和2-NBA）使用类苯甲酰苯胺电荷转移作为探针反应，探测1-氨基萘（1-AN）和2-氨基萘（2-AN）之间的差异。对于在环己烷中所有制备的氨基萘衍生物，发现了异常的长波发射，并且通过观察到随着溶剂极性的增加或取代基的吸电子能力的增加而发生的大幅度红移，将其分配为CT状态。发现CT发射能量与取代基的Hammett常数和1-NBA（-0。45 eV高于2-NBA（-0.35 eV），后者与苯胺衍生物（BAs，-0.345 eV）接近。这表明在1-NBA的CT状态下，电荷分离的程度更高，其中完全放电分离是通过CT发射能量的线性下降率为-1.00的降低电势依赖性建立的。通过观察发现，当对位，间位和对位时，苯甲酰基取代的BA的相应线性斜率保持不变，从而排除了1-NBA和2
• A Convenient and Inexpensive Method for Conversion of Thiocarbonyl Compounds to Their Oxo Derivatives Using Oxone Under Solvent-Free Conditions
  作者：Iraj Mohammadpoor-Baltork、Majid M. Sadeghi、Karim Esmayilpour

  DOI：10.1081/scc-120016359

  日期：2003.1.4

  Abstract A series of thioamides, thioureas and thioesters are transformed to their corresponding carbonyl compounds in good to excellent yields with oxone under solid phase conditions, while thioketones remained unchanged under these conditions.

  摘要 一系列硫代酰胺、硫脲和硫酯在固相条件下与 oxone 一起转化为相应的羰基化合物，产率良好至极好，而硫酮在这些条件下保持不变。
• Copper‐Mediated Aminoquinoline‐Directed Radiofluorination of Aromatic C−H Bonds with K ¹⁸ F
  作者：So Jeong Lee、Katarina J. Makaravage、Allen F. Brooks、Peter J. H. Scott、Melanie S. Sanford

  DOI：10.1002/anie.201812701

  日期：2019.3.4

  A Cu-mediated ortho-C-H radiofluorination of aromatic carboxylic acids that are protected as 8-aminoquinoline benzamides is described. The method uses K18 F and is compatible with a wide range of functional groups. The reaction is showcased in the high specific activity automated synthesis of the RARβ2 agonist [18 F]AC261066.

  描述了被保护为8-氨基喹啉苯甲酰胺的芳香族羧酸的Cu介导的邻位CH氟化。该方法使用K18 F，并且与多种官能团兼容。该反应在RARβ2激动剂[18 F] AC261066的高比活性自动合成中得到展示。
• Efficient and Convenient Deprotection of Thiocarbonyl to Carbonyl Compounds Using 3-Carboxypyridinium and 2,2'-Bipyridinium Chlorochromates in Solution, Dry Media, and under Microwave Irradiation
  作者：Iraj Mohammadpoor-Baltork、Hamid Reza Memarian、Kiumars Bahrami

  DOI：10.1007/s00706-003-0095-0

  日期：2004.4.1

  deprotection reactions is reported. Different types of thioamides, thioureas, thiono esters, and thioketones are deprotected to their corresponding carbonyl compounds with these reagents in good to excellent yields. The reactions were carried out in solution, under solvent-free conditions, and under microwave irradiation. The results show that with both reagents the rates of the reactions and the yields

  报道了3-羧基吡啶鎓（ CPCC ）和2,2'-联吡啶鎓（ BPCC）氯铬酸盐 在脱保护反应中的合成效用 。用这些试剂将不同类型的硫代酰胺，硫脲，硫代酸酯和硫代酮以良好或优异的产率脱保护为其相应的羰基化合物。反应在溶液中，无溶剂条件下和在微波辐射下进行。结果表明，在微波辐射下，两种试剂的反应速率和产率通常最高。
• Transformation of Thioamide Compounds to Corresponding Amides Using 12-Tungstosilicic Acid
  作者：Masoud Nasr-Esfahani、Morteza Montazerozohori、Majid Moghadam、Iraj Mohammadpoor-Baltork、Sareh Moradi

  DOI：10.1080/10426500902758964

  日期：2010.1.29

  12-Tungstosilicic acid (H4SiW12O40) is applied for the conversion of a series of thioamides to their corresponding oxo analogues in excellent yields in acetonitrile. In the case of thioketones, no reaction is observed under these conditions. The reusability of the catalyst also is investigated.

  12-钨硅酸 (H4SiW12O40) 用于在乙腈中以极好的收率将一系列硫代酰胺转化为其相应的氧代类似物。在硫酮的情况下，在这些条件下没有观察到反应。还研究了催化剂的可重复使用性。