N,2-dimethyl-1-naphthalenecarboxamide | 198221-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,2-dimethyl-1-naphthalenecarboxamide
• 英文别名: 2,N-dimethyl-naphthalene-carboxamide；N,2-Dimethyl-1-naphthamide；N,2-dimethylnaphthalene-1-carboxamide
• CAS: 198221-08-8
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: VUSJNQFBXBDQQI-UHFFFAOYSA-N

物化性质

• 熔点：
  177.7-178.6 °C
• 沸点：
  385.7±21.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  N,2-dimethyl-1-naphthalenecarboxamide 、 1-(4-氯苯基)-3-(二甲基氨基)-1-丙酮 、 草酸 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-(4-chlorophenyl)-2-(2-dimethylaminoethyl)-1,2-dihydro-3-oxa-phenanthren-4-one oxalate
  参考文献：
  名称：

  Optimization of isochromanone based urotensin II receptor agonists

  摘要：

  A series of novel isochromanone based urotensin II receptor agonists have been synthesized and evaluated for their activity using a functional cell based assay (R-SAT). Several potent and efficacious derivatives were identified with 3-(3,4-dichlorophenyl)-6,7-dimethyl-3-(2-dimethylaminoethyl) isochroman-1-one (28) being the most potent compound showing an EC50-value of 51 nM, thereby being the most potent compound so far within the isochromanone series. In addition, two other heterocyclic systems (isochromanes and tetrahydroisoquinolinones) were investigated and these derivatives were found to be both potent and efficacious. The activity of the isochromane derivatives implies that the carbonyl group of the isochromanone is not necessary for activity. Furthermore it was found that the geometry of the heterocycles was more important for receptor interaction than the composition of the heteroatoms present. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.041
• 作为产物：
  描述：

  2-甲基萘-1-甲酰氯 、 甲胺 以 四氢呋喃 为溶剂， 反应 0.25h， 以1.3 g的产率得到N,2-dimethyl-1-naphthalenecarboxamide
  参考文献：
  名称：

  Optimization of isochromanone based urotensin II receptor agonists

  摘要：

  A series of novel isochromanone based urotensin II receptor agonists have been synthesized and evaluated for their activity using a functional cell based assay (R-SAT). Several potent and efficacious derivatives were identified with 3-(3,4-dichlorophenyl)-6,7-dimethyl-3-(2-dimethylaminoethyl) isochroman-1-one (28) being the most potent compound showing an EC50-value of 51 nM, thereby being the most potent compound so far within the isochromanone series. In addition, two other heterocyclic systems (isochromanes and tetrahydroisoquinolinones) were investigated and these derivatives were found to be both potent and efficacious. The activity of the isochromane derivatives implies that the carbonyl group of the isochromanone is not necessary for activity. Furthermore it was found that the geometry of the heterocycles was more important for receptor interaction than the composition of the heteroatoms present. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.041

文献信息

• Cobalt-Catalyzed Chemoselective Insertion of Alkene into the Ortho C−H Bond of Benzamide
  作者：Laurean Ilies、Quan Chen、Xiaoming Zeng、Eiichi Nakamura

  DOI：10.1021/ja200645w

  日期：2011.4.13

  Insertion of 1-alkene, 2-alkene, and styrene into the ortho C-H bond of benzamide in the presence of an inexpensive cobalt catalyst, DMPU as a crucial ligand, and cyclohexylmagnesium chloride proceeds smoothly at 25 °C to selectively give the ortho-alkylated product. Notable features of this reaction include the structural variety of the alkene and the amide substrate and the tolerance of functional

  在廉价的钴催化剂存在下，将 1-烯烃、2-烯烃和苯乙烯插入苯甲酰胺的邻 CH 键，DMPU 作为关键配体，环己基氯化镁在 25°C 下顺利进行，选择性地得到邻烷基化的产品。该反应的显着特征包括烯烃和酰胺底物的结构多样性以及对卤化物、烯烃、酯和酰胺基团等官能团的耐受性。
• Manganese-Catalyzed Directed Methylation of C(sp²)–H Bonds at 25 °C with High Catalytic Turnover
  作者：Takenari Sato、Takumi Yoshida、Hamad H. Al Mamari、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/acs.orglett.7b02778

  日期：2017.10.6

  scope, using MeMgBr, a catalytic amount of MnCl2·2LiCl, and an organic dihalide oxidant. The reaction features ambient temperature, low catalyst loading, typically 1%, high catalytic turnover reaching 5.9 × 103, and no need for an extraneous ligand and illustrates a unique catalytic use of simple manganese salts for C–H activation, which so far has relied on catalysis by manganese carbonyls.

  我们在这里报告了使用MeMgBr，催化量的MnCl 2 ·2LiCl和有机二卤化物氧化剂进行的锰催化的CH甲基化反应，具有较大的底物范围。该反应具有环境温度，低催化剂负载（通常为1％），高催化转化率（达到5.9×10 3），不需要外来配体的特点，并说明了简单的锰盐在C–H活化中的独特催化用途，到目前为止，该反应已具有依赖于羰基锰的催化作用。
• Cobalt-Catalyzed Coupling of Alkyl Grignard Reagent with Benzamide and 2-Phenylpyridine Derivatives through Directed C–H Bond Activation under Air
  作者：Quan Chen、Laurean Ilies、Naohiko Yoshikai、Eiichi Nakamura

  DOI：10.1021/ol2011264

  日期：2011.6.17

  Aromatic carboxamides and 2-phenylpyridine derivatives can be ortho-alkylated with Grignard reagents in the presence of a cobalt catalyst and DMPU as a ligand. The reaction proceeds smoothly at room temperature, using air as the sole oxidant. The dialkylated product is selectively obtained when N-methylcarboxamide is employed as a substrate, whereas N-phenyl- or N-isopropylcarboxamide preferentially

  可以在钴催化剂和DMPU作为配体的情况下，使用Grignard试剂对芳族羧酰胺和2-苯基吡啶衍生物进行邻烷基化。使用空气作为唯一的氧化剂，该反应在室温下平稳进行。当使用N-甲基羧酰胺作为底物时，选择性地获得二烷基化产物，而N-苯基-或N-异丙基羧酰胺优先给出单烷基化产物。
• Optimization of isochromanone based urotensin II receptor agonists
  作者：Fredrik Lehmann、Erika A. Currier、Roger Olsson、Jian-Nong Ma、Ethan S. Burstein、Uli Hacksell、Kristina Luthman

  DOI：10.1016/j.bmc.2010.04.041

  日期：2010.7

  A series of novel isochromanone based urotensin II receptor agonists have been synthesized and evaluated for their activity using a functional cell based assay (R-SAT). Several potent and efficacious derivatives were identified with 3-(3,4-dichlorophenyl)-6,7-dimethyl-3-(2-dimethylaminoethyl) isochroman-1-one (28) being the most potent compound showing an EC50-value of 51 nM, thereby being the most potent compound so far within the isochromanone series. In addition, two other heterocyclic systems (isochromanes and tetrahydroisoquinolinones) were investigated and these derivatives were found to be both potent and efficacious. The activity of the isochromane derivatives implies that the carbonyl group of the isochromanone is not necessary for activity. Furthermore it was found that the geometry of the heterocycles was more important for receptor interaction than the composition of the heteroatoms present. (C) 2010 Elsevier Ltd. All rights reserved.