cyanoacetic acid N-phenylhydrazide | 60598-59-6

• 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: cyanoacetic acid N-phenylhydrazide
• 英文别名: Cyanaceto-phenylhydrazid；β-Cyanoacetylphenylhydrazin；N-Cyanoacetylphenylhydrazin；phenylcyanoacetohydrazide；N'-Phenyl-N-cyanacetyl-hydrazin；Cyan-essigsaeure-(N'-phenyl-hydrazid)；2-cyano-N'-phenylacetohydrazide
• CAS: 60598-59-6
• 化学式: C₉H₉N₃O
• mdl: MFCD04222138
• 分子量: 175.19
• InChiKey: IYJOWCCDWGQUAO-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  300.6±34.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyanoacetic acid N-phenylhydrazide 在 溶剂黄146 作用下， 以 异丙醇 为溶剂， 生成 1-(3-chloro-phenyl)-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-quinoline-3-carboxylic acid N'-phenyl-hydrazide
  参考文献：
  名称：

  Pathways for cyclizations of hydrazine-derived 2-(2-cyanovinyl)-3-oxo-cyclohex-1-ene enolates

  摘要：

  The introduction of a hydrazine functionality into 2-(2-cyanovinyl)-3-oxo-cyclohex-1-ene enolates results in their spontaneous cyclizations with participation of the hydrazine moiety. Depending on the reaction conditions used, the hydrazine-derived enolates are transformed into derivatives of 1-arylpyridine-2-one-3-carbonitriles or pyrazoloquinolinones in a one-pot synthesis. They also react with anilines to give the corresponding N1-substituted pyridine-2-one-3-carboxamides. Product characterization was performed by means of spectroscopic and X-ray diffraction studies. In addition, for structure elucidation purposes, a counter synthesis of 1-arylaminopyridine-2-one-3-carboxamide was also carried out. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.052
• 作为产物：
  描述：

  吉非替尼中间体3 、 苯肼 在 乙醚 作用下， 生成 cyanoacetic acid N-phenylhydrazide
  参考文献：
  名称：

  Investigation of Pyrazole Compounds. II.¹ The Synthesis of 1-Phenyl-3-hydroxy-5-pyrazolone Imide

  摘要：

  DOI：

  10.1021/ja01241a017

文献信息

• A Convenient Synthesis Of Substituted 3-Pyrrolin-2-ones from α-Cetols
  作者：Gaguik Melikian、Francis Rouessac、Christian Alexandre

  DOI：10.1080/00397919308013792

  日期：1993.11

  Abstract A simple and efficient method for the preparation of the title compounds is described from cyanoacetamides and 3-hydroxy-3-methyl-2-butanone in the presence of sodium ethylate at room temperature. The 3-carboxamido-N-alkyl-4, 5, 5-trimethyl-5-dihy dro-2H-pyrrol-2-ones lead to unsaturated derivatives by condensation with aldehydes, while hydrogenation give rise to the corresponding pyrrolidin-2-ones

  摘要 描述了在乙醇钠存在下，在室温下，由氰基乙酰胺和 3-羟基-3-甲基-2-丁酮制备标题化合物的一种简单有效的方法。3-甲酰胺基-N-烷基-4, 5, 5-trimethyl-5-dihy dro-2H-pyrrol-2-ones 通过与醛缩合生成不饱和衍生物，而氢化生成相应的 pyrrolidin-2-ones .
• Synthesis of 5-Amino-1,10b-dihydro-2H-chromeno[3,4-c]pyridine-2,4(3H)-diones from Coumarins and Cyanoacetamides under Basic Conditions
  作者：Ornelio Rosati、Massimo Curini、Maria Marcotullio、Caroline Pelucchini、Antonio Procopio、Gildas Oball-Mond

  DOI：10.1055/s-0029-1217128

  日期：2010.1

  The reaction of various coumarins with cyanoacetamide derivatives under basic conditions (sodium ethoxide, piperidine or 2,2,6,6-tetramethylpiperidine), proceeds via an interesting process which involves skeletal rearrangement of the coumarin, a Michael addition and two cyclizations to afford 5-amino-1,10b-dihydro-2H-chromeno[3,4-c]pyridine-2,4(3H)-diones. The same reaction in the presence of N,N¢-ethane-1

  各种香豆素与氰基乙酰胺衍生物在碱性条件下（乙醇钠，哌啶或2,2,6,6-四甲基哌啶）的反应是通过一个有趣的过程进行的，该过程涉及香豆素的骨架重排，迈克尔加成和两个环化反应得到5 -氨基-1,10b-二氢-2 H-苯并[3,4- c ]吡啶-2,4（3 H）-二酮。在N，N ¢-乙烷-1,2-二基双（2-氰基乙酰胺）存在下的相同反应，得到相应的单和双5-氨基-1,10b-二氢-2 H -chromeno [3,4- c ]吡啶-2,4（3 H）-二酮。 香豆素-迈克尔加成-杂环-环化-chromenes
• Heterocyclen-Synthesen mit Monothiomalonsäure-Amiden: Synthese von 3-Oxo-2,3-dihydroisothiazolo [5,4-<i>b</i>] pyridinen und 3-Oxo-2,3-dihydroisothiazolo[5,4-<i>d</i>]pyrimidinen
  作者：Wolfgang Schaper

  DOI：10.1055/s-1985-31365

  日期：——

  Heterocyclic Syntheses with Monothiomalonic Amides: Synthesis of 3-Oxo-2,3-dihydroisothiazolo[5,4-b]pyridines and 3-Oxo-2,3-dihydroisothiazolo[5,4-d]pyrimidines The monothiomalonic acid amides 5, prepared from cyanoacetamides 4 and hydrogen sulphide, react with diketones 6 or aldehyde derivatives 7 to give the 2-thioxo-1,2-dihydropyridine-3-carboxamides 8 which can be cyclised to the 3-oxo-2,3-dihydroisothiazolo[5,4-d]pyridines 2. Amides 5 also react with s-triazine to give the 3-oxo-2,3-dihydroisothiazolo [5,4-d]pyrimidines 3.

  用单硫代丙二酸酰胺合成杂环化合物： 3-氧代-2,3-二氢异噻唑并[5,4-b]吡啶和 3-氧代-2,3-二氢异噻唑并[5,4-d]嘧啶的合成 由氰基乙酰胺 4 和硫化氢制备的单硫代丙二酸酰胺 5 与二酮 6 或醛衍生物 7 反应，得到 2-硫酮-1,2-二氢吡啶-3、与二酮 6 或醛衍生物 7 反应生成 2-硫酮-1,2-二氢吡啶-3-羧酰胺 8，后者可环化成 3-氧代-2,3-二氢异噻唑并[5,4-d]吡啶 2。酰胺 5 还能与 s-三嗪反应生成 3-氧代-2,3-二氢异噻唑并[5,4-d]嘧啶 3。
• Carbon Disulfide in Heterocyclic Organic Synthesis; Synthesis of Polyfunctionally Substituted Sulfur and Nitrogen Heteroaromatics
  作者：Salem E. Zayed

  DOI：10.1080/10426500701407722

  日期：2007.7.19

  Reaction of cayno acetamdie with carbon disulphide in alkaline medium, e.g., potassium hydroxide, or potassium ter butoxide gave the gem-dithiol (1). While in presence of ammonium hydroxide the ammonium salt (2) was obtained. Reactions of (1) or (2) with different reagents in different mediums gave pyridine, pyrimidines, thiophene, and thiopyranones derivatives.

  在碱性介质（例如氢氧化钾或三丁醇钾）中，cayno acetamdie 与二硫化碳反应得到偕二硫醇 (1)。在氢氧化铵存在下得到铵盐(2)。(1) 或 (2) 与不同试剂在不同介质中的反应得到吡啶、嘧啶、噻吩和噻喃酮衍生物。
• Devani; Shishoo; Pathak, Arzneimittel-Forschung/Drug Research, 1977, vol. 27, # 9, p. 1652 - 1655
  作者：Devani、Shishoo、Pathak、Parikh、Radhakrishnan、Padhya

  DOI：——

  日期：——