10-(dicyanomethylidene)-9(10H)-anthrone hydrazone | 156755-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-(dicyanomethylidene)-9(10H)-anthrone hydrazone
• 英文别名: 10-dicyanomethylene-9-anthrone hydrazone；10-dicyanomethylene-anthrone hydrazone；Propanedinitrile, (10-hydrazono-9(10H)-anthracenylidene)-；2-(10-hydrazinylideneanthracen-9-ylidene)propanedinitrile
• CAS: 156755-16-7
• 化学式: C₁₇H₁₀N₄
• 分子量: 270.293
• InChiKey: LDQYWCSUCBIOQT-UHFFFAOYSA-N

物化性质

• 沸点：
  468.4±33.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  86
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-(dicyanomethylidene)-9(10H)-anthrone hydrazone 在 硫酸 、 乙酸酐 作用下， 反应 14.0h， 以84%的产率得到10-dicyanomethylene-9,10-dihydroanthracen-9-one
  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
• 作为产物：
  描述：

  2,2'-(9,10-蒽二亚基)-双丙二腈 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到10-(dicyanomethylidene)-9(10H)-anthrone hydrazone
  参考文献：
  名称：

  A novel reaction of 11,11,12,12-tetracyanoanthraquinodimethane: The formation of 10-dicyanomethylene-anthrone hydrazone

  摘要：

  A novel reaction of 11,11,12,12-tetracyanoanthraquinodimethane - its transformation into 10-dicyanomethylene-anthrone hydrazone by reaction with hydrazine - is reported. This hydrazone seems to be a convenient starting material in the synthesis of anthracene derivatives and compounds incorporating anthracenic fragments, but is itself as a conjugated donor acceptor system a material with interesting physical properties.

  DOI：

  10.1007/bf00811847

文献信息

• Amphoteric Quinone–azine–cyclopentadithiophene System
  作者：Masatoshi Kozaki、Hiroaki Igarashi、Keiji Okada

  DOI：10.1246/cl.2004.156

  日期：2004.2

  Various quinoid groups have been connected with the cyclopentadithiophene (CPDT) skeleton via azine linkage to form a new D–π–A system. These compounds revealed weak absorptions extending to 590–630 nm, corresponding to small HOMO–LUMO gaps of 1.97–2.10 eV. Their reduction potentials were strongly dependent on the quinone moieties, whereas the oxidation potentials were controlled by the CPDT moiety. Some of these compounds underwent oxidative polymerization under electrochemical conditions to yield polymers with a highly amphoteric character.

  各种醌基通过叠氮连接与环戊二烯噻吩（CPDT）骨架相连，形成了一种新的 D-π-A 系统。这些化合物显示出延伸至 590-630 纳米的微弱吸收，对应于 1.97-2.10 eV 的小 HOMO-LUMO 间隙。它们的还原电位在很大程度上取决于醌分子，而氧化电位则由 CPDT 分子控制。其中一些化合物在电化学条件下发生氧化聚合，生成具有高度两性特性的聚合物。
• 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.
• 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：——
• A novel reaction of 11,11,12,12-tetracyanoanthraquinodimethane: The formation of 10-dicyanomethylene-anthrone hydrazone
  作者：H. Falk、A. F. Vaisburg

  DOI：10.1007/bf00811847

  日期：1994.5

  A novel reaction of 11,11,12,12-tetracyanoanthraquinodimethane - its transformation into 10-dicyanomethylene-anthrone hydrazone by reaction with hydrazine - is reported. This hydrazone seems to be a convenient starting material in the synthesis of anthracene derivatives and compounds incorporating anthracenic fragments, but is itself as a conjugated donor acceptor system a material with interesting physical properties.
• 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.