3-acetylcyclopropane-1,1,2,2,-tetracarbonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetylcyclopropane-1,1,2,2,-tetracarbonitrile
• 英文别名: 3-acetylcyclopropane-1,1,2,2-tetracarbonitrile
• 化学式: C₉H₄N₄O
• mdl: MFCD01305738
• 分子量: 184.157
• InChiKey: PJCWOHOXULIYEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetylcyclopropane-1,1,2,2,-tetracarbonitrile 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 sodium 2-acetyl-1,1,3,3-tetracyanoprop-2-en-1-ide
  参考文献：
  名称：

  One-Pot Synthesis of 2-Alkylsulfanyldihydrofuran Derivatives from Tetracyanocyclopropyl Ketones

  摘要：

  Successive treatment of 3-acylcyclopropane-1,1,2,2-tetracarbonitriles with sodium hydrogen carbonate and alkylmercaptan in water environment results in the formation of 2-(5-amino-2-aryl-2-alkyl-sulfanyl-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles.

  DOI：

  10.1134/s1070428018050226
• 作为产物：
  描述：

  2-溴丙二腈 、 丙酮醛 在 丙二腈 作用下， 以 异丙醇 为溶剂， 反应 0.25h， 生成 3-acetylcyclopropane-1,1,2,2,-tetracarbonitrile
  参考文献：
  名称：

  New procedures for preparing 2,2,3,3-tetracyanocyclopropyl ketones

  摘要：

  New procedures were developed for preparing 2,2,3,3-tetracyanocyclopropyl ketones, based on reactions of substituted glyoxals with bromomalononitrile.

  DOI：

  10.1134/s1070427209080217

文献信息

• Synthesis of 2,2,3,3-tetracyanocyclopropyl ketones and their reactions with oxygen-centered nucleophiles
  作者：I. N. Bardasov、O. V. Kayukova、Ya. S. Kayukov、O. V. Ershov、O. E. Nasakin、V. A. Tafeenko

  DOI：10.1134/s1070428009090048

  日期：2009.9

  procedure for the synthesis of 2,2,3,3-tetracyanocyclopropyl ketones has been developed on the basis of three-component Wideqvist reaction of dihydroxymethyl ketones, 2-bromomalononitrile, and malononitrile. The presence of five electron-withdrawing groups in the resulting cyclopropyl ketones determines high acidity of proton in the cyclopropane ring. Facile deprotonation by the action of bases promotes

  基于二羟基甲基酮，2-溴丙二腈和丙二腈的三组分Wideqvist反应，已经开发了合成2,2,3,3-四氰基环丙基酮的方法。所得环丙基酮中五个吸电子基团的存在决定了环丙烷环中质子的高酸度。通过碱的作用容易的去质子化促进三元环的打开，形成1,1,3,3-四氰基丙烯或（在存在醇或肟的情况下）[2-烷氧基（氨基氧基）-5-氨基-4-氰基呋喃-3（2 H）-亚烷基]丙二腈。与丙酮肟的反应不伴有三元环的裂解，亲核攻击是针对反式中的氰基相对于羰基的位置给出相应的（1 R *，5 S *，6 R *）-4-氨基-2,2-双（丙-2-亚氨基氨基氧基）-3-氮杂双环[3.1.0]十六烷基-3-烯-1,5-二碳腈。
• Reaction of 2,2,3,3-tetracyanocyclopropyl ketones with sodium and potassium hydroxides
  作者：Ya. S. Kayukov、I. N. Bardasov、S. V. Karpov、O. V. Ershov、O. E. Nasakin、O. V. Kayukova、V. A. Tafeenko

  DOI：10.1134/s1070428012110073

  日期：2012.11

  Reaction of 2,2,3,3-tetracyanocyclopropyl ketones with water solution of sodium hydroxide after neutralization with sulfuric acid leads to the formation of 4-amino-1-hydroxy-3,6-dioxo-2,3,5,6-tetrahydro-1Hpyrrolo[3,4-c]pyridine-7-carbonitriles. Pivaloyltetracyanocyclopropane reacts in another way and is converted into sodium 6a-tert-butyl-3,4-dicyano-5-oxo-1,5,6,6a-tetrahydropyrrolo[2,3-b]pyrrol-2-olate

  用硫酸中和后，使2,2,3,3-四氰基环丙基酮与氢氧化钠水溶液反应，导致形成4-氨基-1-羟基-3,6-二氧代-2,3,5,6-四氢-1 H吡咯并[3,4- c ]吡啶-7-腈。新戊酰基四氰基环丙烷以另一种方式反应，并转化为3,4-二氰基-5-氧杂-1,5,6,6a-四氢吡咯并[2,3 - b ]吡咯-2-油酸酯的6a-叔丁基钠。1-苯甲酰基-1-甲基环丙烷-2,2,3,3-四甲腈与氢氧化钠反应，保留三元环并形成11-甲基-4-苯基-3,5,9-三氮杂四环[5.3] .1.01,7.0 4,11 ]十一烷-2,6,8,10-四酮。
• One-pot synthesis of 2-(2-alkoxy-5-amino-4-cyano-2-methylfuran-3(2H)-ylidene)malononitriles
  作者：I. N. Bardasov、O. V. Kayukova、Ya. S. Kayukov、O. V. Ershov、M. Yu. Belikov、O. E. Nasakin

  DOI：10.1007/s10593-009-0388-2

  日期：2009.9

  A new preparative method was developed for the synthesis of 2-(2-alkoxy-5-amino-4-cyano-2-methyl3(2H)-ylidene) malononitriles in a single stage from readily obtainable reagents.
• Reaction of 2,2,3,3-tetracyanocyclopropyl ketones with water
  作者：Ya. S. Kayukov、I. N. Bardasov、O. V. Ershov、O. E. Nasakin、O. V. Kayukova、V. A. Tafeenko

  DOI：10.1134/s1070428012040033

  日期：2012.4

  3-Benzoylcyclopropane-1,1,2,2-tetracarbonitrile reacted with water to give 2-benzoyl-1,3-dicyanocyclopropane-1-carboxamide as a result of hydrolysis of the cyano group in the trans position with respect to the carbonyl group and subsequent decarboxylation. The reaction of 3-benzoyl-3-methylcyclopropane-1,1,2,2-tetracarbonitrile with water involved heterocyclization with participation of the carbonyl group and cis-cyano groups, leading to 8-methyl-3,6-dioxo-1-phenyl-2,7-diazatricyclo[3.2.1.0(4,8)]octane-4,5-dicarbonitrile. Hydrolysis of 3-alkylcyclopropane-1,1,2,2-tetracarbonitrile followed both reaction paths to produce mixtures of products, including 7-alkyl-4-amino-7-hydroxy-1,9-dioxo-3,8-diazatricyclo[4.3.0.0(1,5)]non-3-ene-5-carbonitriles. In all cases, the three-membered ring was retained.
• Sheverdov; Ershov; Nasakin, Russian Journal of General Chemistry, 2000, vol. 70, # 8, p. 1251 - 1253
  作者：Sheverdov、Ershov、Nasakin、Selyunina、Tikhonova、Chernushkin、Khrustalev

  DOI：——

  日期：——