1-甲基-N-苯基咪唑-2-甲酰胺 | 35342-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-甲基-N-苯基咪唑-2-甲酰胺
• 英文名称: 1-methyl-N-phenyl-1H-imidazole-2-carboxamide
• 英文别名: 1-methyl-1H-imidazole-2-carbanilide；2-(1-methyl)imidazoanilide；1-methyl-1H-imidazole-2-carboxylic acid anilide；1-methyl-imidazole-2-carboxanilide；N-Phenyl-2-(1-methyl)-imidazol-carboxamid；1H-Imidazole-2-carboxamide, 1-methyl-N-phenyl-；1-methyl-N-phenylimidazole-2-carboxamide
• CAS: 35342-94-0
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: JJZPMYSCNBKVOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  104-106 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基-N-苯基咪唑-2-甲酰胺 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以92%的产率得到N,1-dimethyl-N-phenyl-1H-imidazole-2-carboxamide
  参考文献：
  名称：

  带有咪唑环的芳香酰胺的构象性质和酸诱导的反式-顺式酰胺转换

  摘要：

  带有仲酰胺键的芳香酰胺在晶体和溶液中均以反式构象存在，而N-甲基化衍生物的构象在晶体中为顺式，在各种溶剂中以顺式构象为主。 N-烷基化苯甲酰苯胺的顺式构象偏好提供了获得芳香族折叠体的途径，例如采用动态螺旋结构的低聚( N-烷基-对苯甲酰胺)。在此，检查了晶体和溶液中咪唑取代酰胺的构象性质。咪唑取代酰胺2a和4a在溶液中主要以顺式构象存在。 N-甲基-N- (1-甲基-1H-咪唑-4-基)苯甲酰胺( 4a )的顺式构象异构体比例小于N ,1-二甲基-N-苯基-1H-咪唑-2-甲酰胺( 2a )或N-甲基苯甲酰苯胺，但取代基的引入强烈影响构象异构体比率。咪唑环上带有吸电子基团的化合物6a和7a主要以反式形式存在。另一方面，在苯环上引入吸电子基团或在4a的酰胺氮上引入大体积取代基增加了顺式构象异构体的比例。此外，通过添加酸， N-烷基化的N-咪唑酰胺的主要构象异构体从顺式转变为反式。这些结果表明

  DOI：

  10.1021/acs.joc.2c01295
• 作为产物：
  描述：

  N-acetyl-1-methyl-2-(phenylcarbamoyl)-1H-imidazolium-3-aminide 在 盐酸 、 sodium nitrite 作用下， 反应 0.5h， 生成 1-甲基-N-苯基咪唑-2-甲酰胺
  参考文献：
  名称：

  Phenylcarbamoylation of N-Acetyl-1,2,4-triazolium-4-aminides Revisited

  摘要：

  The reaction of N-acetyl-1,2,4-triazolium-4-aminides (I, i.e. 1Aa-d) with phenyl isocyanate affords ring functionalized products (4a-d) rather than linear adducts (II). Analogous compounds are obtained from the triazolium-1-aminide (1Ae) and the imidazolium congener (W). Twofold carbamoylation to give products of type (8) occurs on reaction of aminotriazolium salts (7A) in the presence of base. Azoliums having methyl at C(5)/(2) are inert throughout (B series).

  DOI：

  10.3987/com-06-10836

文献信息

• Iridium-Catalyzed Direct Amidation of Imidazoles at the C-2 Position with Isocyanates in the Presence of Hydrosilanes Leading to Imidazole-2-Carboxamides
  作者：Yoshiya Fukumoto、Motohiro Shiratani、Hikaru Noguchi、Naoto Chatani

  DOI：10.1055/a-1375-5283

  日期：2021.9

  Regioselective coupling reaction of N-substituted imidazoles with isocyanates in the presence of a stoichiometric amount of hydrosilanes catalyzed by Ir4(CO)12 to give imidazole-2-carboxamides is reported. Imidazoles bearing an (O-silyl)carboximidate group at the 2-position appear to be initially formed in the reaction; these are then hydrolyzed to the final products in situ. The addition of the hydrosilane

  报道了在化学计量的Ir4（CO）12催化的氢硅烷存在下，N-取代的咪唑与异氰酸酯的区域选择性偶联反应，得到了咪唑-2-甲酰胺。在反应中似乎最初形成了在2位带有（O-甲硅烷基）碳亚氨酸酯基的咪唑; 然后将它们原位水解为最终产物。加氢硅烷对于进行催化反应是必不可少的。咪唑环上的取代基对反应没有影响，除了某些大的取代基（例如4位的t Bu和Ph基）。三唑类化合物，例如4-甲基-4H-1,2,4-三唑和1-甲基-1H-1,2,4-三唑也适用于此CH酰胺化反应，后者反应在碳原子上进行区域选择性反应在环的sp3和sp2氮原子之间，
• Di-<i>tert</i>-butyl Dicarbonate and 4-(Dimethylamino)pyridine Revisited. Their Reactions with Amines and Alcohols¹
  作者：Yochai Basel、Alfred Hassner

  DOI：10.1021/jo000257f

  日期：2000.10.1

  The reaction of BOC2O in the presence and absence of DMAP was examined with some amines, alcohols, diols, amino alcohols, and aminothiols. Often, unusual products were observed depending on the ratio of reagents, reaction time, polarity of solvent, pK(a) of alcohols, or type of amine (primary or secondary). In reactions of aliphatic alcohols with BOC2O/DMAP, we isolated for the first time carbonic-carbonic anhydride intermediates; this helps explain the formation of symmetrical carbonates in addition to the O-BOC products. In the case of secondary amines, we succeeded to isolate unstable carbamic-carbonic anhydride intermediates that in the presence of DMAP led to the final N-BOC product. The effect of N-methylimidazole in place of DMAP was also examined.
• α-Nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid
  作者：Patrick Y.S Lam、Sophie Deudon、Elisabeth Hauptman、Charles G Clark

  DOI：10.1016/s0040-4039(01)00203-9

  日期：2001.3

  Heteroarylcarboxamides containing a-nitrogens undergo copper-promoted N-phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air. Arylboronic acid can substitute for phenyl trimethylsiloxane as the organometalloid. The ol-heteroatom chelating effect is in the decreasing order of N>O, S. This discovery opens up the possibility of using other alpha -nitrogen functional groups to direct the N-arylation of peptides and simple amides under conditions as mild as that of amide bond formation. (C) 2001 Dupont Pharmaceutical Company. Published by Elsevier Science Ltd. All rights reserved.
• Phenylcarbamoylation of N-Acetyl-1,2,4-triazolium-4-aminides Revisited
  作者：Dietrich Moderhack、Matthias Noreiks

  DOI：10.3987/com-06-10836

  日期：——

  The reaction of N-acetyl-1,2,4-triazolium-4-aminides (I, i.e. 1Aa-d) with phenyl isocyanate affords ring functionalized products (4a-d) rather than linear adducts (II). Analogous compounds are obtained from the triazolium-1-aminide (1Ae) and the imidazolium congener (W). Twofold carbamoylation to give products of type (8) occurs on reaction of aminotriazolium salts (7A) in the presence of base. Azoliums having methyl at C(5)/(2) are inert throughout (B series).
• Conformational Properties of Aromatic Amides Bearing Imidazole Ring and Acid-Induced <i>Trans</i>–<i>Cis</i> Amide Switching
  作者：Chiharu Takubo、Sakiko Kimura、Mami Ichinomiya、Arisa Hayakawa、Mako Murata、Ko Urushibara、Hyuma Masu、Kosuke Katagiri、Masatoshi Kawahata、Mayumi Kudo、Isao Azumaya、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1021/acs.joc.2c01295

  日期：——

  bearing secondary amide bond exist in trans conformation both in the crystal and in solution, whereas the conformation of the N-methylated derivatives is cis in the crystal and predominantly cis in various solvents. The cis conformational preference of N-alkylated benzanilide provides access to aromatic foldamers such as oligo(N-alkyl-p-benzamide)s, which adopt dynamic helical structures. Here, the conformational

  带有仲酰胺键的芳香酰胺在晶体和溶液中均以反式构象存在，而N-甲基化衍生物的构象在晶体中为顺式，在各种溶剂中以顺式构象为主。 N-烷基化苯甲酰苯胺的顺式构象偏好提供了获得芳香族折叠体的途径，例如采用动态螺旋结构的低聚( N-烷基-对苯甲酰胺)。在此，检查了晶体和溶液中咪唑取代酰胺的构象性质。咪唑取代酰胺2a和4a在溶液中主要以顺式构象存在。 N-甲基-N- (1-甲基-1H-咪唑-4-基)苯甲酰胺( 4a )的顺式构象异构体比例小于N ,1-二甲基-N-苯基-1H-咪唑-2-甲酰胺( 2a )或N-甲基苯甲酰苯胺，但取代基的引入强烈影响构象异构体比率。咪唑环上带有吸电子基团的化合物6a和7a主要以反式形式存在。另一方面，在苯环上引入吸电子基团或在4a的酰胺氮上引入大体积取代基增加了顺式构象异构体的比例。此外，通过添加酸， N-烷基化的N-咪唑酰胺的主要构象异构体从顺式转变为反式。这些结果表明