2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile | 159433-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile
• 英文别名: 9-diazo-10-(dicyanomethylene)-9,10-dihydroanthracene；10-Dicyanomethylene-9-diazo-9,10-dihydroanthracene；2-(10-diazoanthracen-9-ylidene)propanedinitrile
• CAS: 159433-46-2
• 化学式: C₁₇H₈N₄
• 分子量: 268.277
• InChiKey: RIQHSDNFCZDKDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile 在 甲酸 、 三乙胺 作用下， 以98%的产率得到9-蒽乙腈
  参考文献：
  名称：

  Concerning the reaction of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile and related compounds with the cryptohydride system formic acid-triethylamine

  摘要：

  The reaction of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile (1) with the cryptohydride system formic acid - triethylamine was studied. The reaction product turned out to be anthracen-9-yl-acetonitrile (2a) instead of the expected 10-dicyanomethyl-9,10-dihydro-anthracene-9-yl formate. Compounds related to 1 yielded in this reaction the corresponding 10-substituted anthracen-9-yl-acetonitriles. A mechanism of this reaction is proposed. The product of the formic acid promoted decomposition of 1, compound 3b, as well as its tautomer 4b were also obtained.

  DOI：

  10.1007/bf00807170
• 作为产物：
  描述：

  10-(dicyanomethylidene)-9(10H)-anthrone hydrazone 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以61%的产率得到2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile
  参考文献：
  名称：

  On the chemical nature of 10-dicyanomethylene-anthrone hydrazone

  摘要：

  The chemical nature of 10-dicyanomethylene-9-anthrone hydrazone was examined. It was shown that this compound bearing the conjugated ylidenemalononitrile fragment and hydrazonic moiety did not undergo transformations characteristic of ylidenemalonitriles, e.g., reduction and Michael addition, but possesses properties typical for hydrazones. Thus it could be hydrolyzed, acetylated, oxidized to yield the diazo compound, and reacted with acetone to form the corresponding azine. These properties were interpreted using semiempirical (AM1) and force field calculations.

  DOI：

  10.1007/bf00811520

文献信息

• On the chemical nature of 10-dicyanomethylene-anthrone hydrazone
  作者：A. F. Vaisburg、C. Etzlstorfer、H. Falk

  DOI：10.1007/bf00811520

  日期：1994.10

  The chemical nature of 10-dicyanomethylene-9-anthrone hydrazone was examined. It was shown that this compound bearing the conjugated ylidenemalononitrile fragment and hydrazonic moiety did not undergo transformations characteristic of ylidenemalonitriles, e.g., reduction and Michael addition, but possesses properties typical for hydrazones. Thus it could be hydrolyzed, acetylated, oxidized to yield the diazo compound, and reacted with acetone to form the corresponding azine. These properties were interpreted using semiempirical (AM1) and force field calculations.
• Vaisburg A. F., Etzlstorfer C., Falk H., Monatsh. Chem, 125 (1994) N 10, S 1121- 1127
  作者：Vaisburg A. F., Etzlstorfer C., Falk H.

  DOI：——

  日期：——
• Concerning the reaction of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile and related compounds with the cryptohydride system formic acid-triethylamine
  作者：A. F. Vaisburg、A. M. Amer、H. Falk

  DOI：10.1007/bf00807170

  日期：——

  The reaction of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile (1) with the cryptohydride system formic acid - triethylamine was studied. The reaction product turned out to be anthracen-9-yl-acetonitrile (2a) instead of the expected 10-dicyanomethyl-9,10-dihydro-anthracene-9-yl formate. Compounds related to 1 yielded in this reaction the corresponding 10-substituted anthracen-9-yl-acetonitriles. A mechanism of this reaction is proposed. The product of the formic acid promoted decomposition of 1, compound 3b, as well as its tautomer 4b were also obtained.
• 2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile: A convenient precursor of 9,10-disubstituted anthracenes
  作者：A. F. Vaisburg、N. M�ller、H. Falk

  DOI：10.1007/bf00807169

  日期：——

  The acid promoted decomposition of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile in the presence of water, methanol, ethanol, acetic and propionic acid, ethyl thioglycolate, p-thiocresole, and acetyl acetone yielding 9,10-disubstituted 9,10-dihydroanthracenes was investigated. Treatment of the reaction products with tri-ethyl amine followed by hydrochloric acid caused their tautomerization to the corresponding 9,10-disubstituted anthracenes. A mechanism for this:reaction is proposed. The first example of an intermolecular C-C-bond formation during the protic acid promoted decomposition of a diazo compound in the presence of CH-acids was found. An improved procedure for the preparation of the starting diazo compound, which may serve as a convenient precursor of 9,10-disubstituted anthracenes, is described.