N-(4-chlorophenyl)-2-cyano-N-methylacetamide | 1134192-49-6

• 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: N-(4-chlorophenyl)-2-cyano-N-methylacetamide
• CAS: 1134192-49-6
• 化学式: C₁₀H₉ClN₂O
• 分子量: 208.647
• InChiKey: BTQFFGLQWHGXFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-2-cyano-N-methylacetamide 在 硫酸 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 以84%的产率得到7-chloro-3,4-dihydro-4-methyl-3-oxoquinoxaline-2-carbonitrile-1-oxide
  参考文献：
  名称：

  Highly Efficient Synthesis of Quinoxalinone-N-oxide via Tandem Nitrosation/Aerobic Oxidative C–N Bond Formation

  摘要：

  An efficient method for constructing quinoxalinone-N-oxides from cyanoacetanilides has been developed. This transformation can be achieved using inexpensive reagents and molecular oxygen under mild conditions, thus offering a practical pathway to quinoxalinone-containing pharmaceuticals such as ataquimast and opaviraline.

  DOI：

  10.1021/ol202760c
• 作为产物：
  描述：

  4-氯-N-甲基苯胺 、 氰乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以53%的产率得到N-(4-chlorophenyl)-2-cyano-N-methylacetamide
  参考文献：
  名称：

  2-Cyano-2- diazo - N -phenyl-acetamides通过环化碳插入和随后的自由基氧化反应制得的3-烷基过氧-3-氰基-吲哚

  摘要：

  据报道，由易于制备的2-氰基-2-重氮-乙酰胺合成3-过氧取代的羟吲哚的无过渡金属一锅顺序。两步串联过程包括高效的分子内热C–H-卡宾插入，然后是四丁基碘化铵（TBAI）催化的自由基C3-过氧官能化。该协议可轻松访问新型的3-氰基-3-过氧二取代的羟吲哚。证明了对酰胺和醇的有用转化。

  DOI：

  10.1021/acs.orglett.6b00367

文献信息

• One-Pot Synthesis of Quinoxalinones via Tandem Nitrosation/Cyclization of <i>N</i>-Aryl Cyanoacetamides
  作者：Fang Wang、Bo-Lun Hu、Lizhi Liu、Hai-Yong Tu、Xing-Guo Zhang

  DOI：10.1021/acs.joc.7b01930

  日期：2017.10.20

  A new one-pot strategy for the synthesis of quinoxalin-2-ones from the tandem nitrosation/cyclization reaction of N-aryl cyanoacetamides with tert-butyl nitrite has been developed. The dehydrogenative N-incorporation is achieved through a sequence of nitrosation, tautomerization, and cyclization, affording quinoxalin-2-ones in moderate to good yields with good functional group tolerance.

  已经开发出一种新的一锅法，该方法由N-芳基氰基乙酰胺与亚硝酸叔丁酯的串联亚硝化/环化反应合成喹喔啉-2-酮。通过一系列的亚硝化，互变异构化和环化作用实现脱氢N结合，以中等至良好的收率提供喹喔啉-2-酮，并具有良好的官能团耐受性。
• α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones
  作者：Yusuke Kobayashi、Terue Nakatani、Rie Tanaka、Mari Okada、Eri Torii、Takashi Harayama、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2011.03.040

  日期：2011.5

  The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via alpha-dimethylaminomethylenation, which promoted the subsequent Houben-Hoesch-type cyclization. Both alpha-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved. (C) 2011 Elsevier Ltd. All rights reserved.
• Metal-Free Synthesis of 2-Oxindoles via PhI(OAc)₂-Mediated Oxidative C–C Bond Formation
  作者：Jinglei Lv、Daisy Zhang-Negrerie、Jun Deng、Yunfei Du、Kang Zhao

  DOI：10.1021/jo4025539

  日期：2014.2.7

  The series of 3-monofunctionalized 2-oxindoles 2 were conveniently synthesized from reactions between anilide 1 and phenyliodine(III) diacetate (PIDA) through hypervalent iodine mediated C(sp(2))-C(sp(2)) bond formation followed by a subsequent deacylation reaction. This metal-free method, shown to provide direct access to an important oxindole intermediate, could be applied to the total synthesis of naturally occurring horsfiline.
• Triflic anhydride-mediated tandem formylation/cyclization of cyanoacetanilides: a concise synthesis of glycocitlone alkaloids
  作者：Yusuke Kobayashi、Takashi Harayama

  DOI：10.1016/j.tetlet.2009.09.073

  日期：2009.12

  A method is presented for the concise synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones through triflic anhydride-mediated tandem formylation/cyclization of cyanoacetanilides. This tandem process was successfully used for the rapid syntheses of glycocitlones A and C. (C) 2009 Elsevier Ltd. All rights reserved.
• A Concise and Versatile Synthesis of Viridicatin Alkaloids from Cyanoacetanilides
  作者：Yusuke Kobayashi、Takashi Harayama

  DOI：10.1021/ol900255g

  日期：2009.4.2

  The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.