2-diazo-1,3-dicyano-6-oxo-2,6-azulenequinone | 53535-47-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-diazo-1,3-dicyano-6-oxo-2,6-azulenequinone
• 英文别名: 1,3-Dicyano-2-diazo-2,6-azulenequinone；2-diazo-1,3-dicyanoazulen-6(2H)-one；1,3-Dicyano-2-diazo-2,6-azulenchinon；1,3-Dicyano-2-diazonioazulen-6-olate
• CAS: 53535-47-0
• 化学式: C₁₂H₄N₄O
• 分子量: 220.19
• InChiKey: MOQCKDDDIANYHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-diazo-1,3-dicyano-6-oxo-2,6-azulenequinone 在 乙醇 作用下， 反应 3.0h， 以82%的产率得到2-ethoxy-6-hydroxy-1,3-dicyanoazulene
  参考文献：
  名称：

  Wun, Wu-Che; Huang, Tian-Chyuan; Lin, Shih-Jue, Journal of the Chinese Chemical Society, 1993, vol. 40, # 6, p. 593 - 596

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Amino-6-bromo-1,3-dicyanoazulene 在 硫酸 、 sodium nitrite 作用下， 以80%的产率得到2-diazo-1,3-dicyano-6-oxo-2,6-azulenequinone
  参考文献：
  名称：

  Formation and structure of 2-diazo-2,4-azulenequinone derivatives

  摘要：

  The diazotization of methyl (and ethyl) 2-amino-3-cyano-4-methoxy(and ethoxy)azulene-1-carboxylate (1-4) was examined to determine whether the products are 2-diazo-2,4-azulenequinone derivatives (B) or azulene-2-diazonium-1-carboxylate derivatives (C). Since diazotization of 1 and 2 gave the same diazo compound 5 and diazotization of both 3 and 4-gave diazo compound 6, the diazo compounds are deduced to not be azulene-2-diazonium-1-carboxylate derivatives (7 and 8), but rather to be 2-diazo-2,4-azulenequinone derivatives (5 and 6). The diazo carbons of both 5 and 6 show C-13 NMR signals at delta 66.3, and their carbonyl carbons resonate at 6 181.1, in good agreement with a 2-diazo-2,4-azulenequinone structure. The structures of diazo compounds 24 and 25, which we have previously reported,(1) are reexamined on the basis of the analysis of their C-13 NMR spectra. The contribution of a quinoid structure and a diazoazulenolate structure to 5, 6, 24, and 25 is discussed by comparison of their C-13 NMR spectral data with those of 4-diazo-2,5-cyclohexadien-1-one derivatives. It is concluded that the contribution of the quinoid structure is larger than that of the diazoazulenolate structure.

  DOI：

  10.1021/jo00123a031

文献信息

• A New Convenient Synthesis of 1,2′-Biazulenes by Photolysis of 2-Diazo-1,3-dicyanoazulen-6(2<i>H</i>)-one with Azulene Derivatives
  作者：Shih-Jue Lin、Shuan-Ya Jiang、Tian-Chyuan Huang、Cheng-Shyan Dai、Pai-Feng Tsai、Hitoshi Takeshita、Yun-Sha -Lin、(the late) Tetsuo Nozoe

  DOI：10.1246/bcsj.70.3071

  日期：1997.12

  A photolysis of 2-diazo-1,3-dicyanoazulen-6(2H)-one in the presence of azulene derivatives in anhydrous ethyl acetate solution afforded 1,2′-biazulene derivatives, which are otherwise difficult to obtain, in good yields, nearly 90% or more. Accompanying by-products, 1,3-dicyanoazulen-6-ol and 2,5′-biazulene derivatives, were also characterized.

  2-diazo-1,3-dicyanoazulen-6(2H)-one 在 azulene 衍生物存在下在无水乙酸乙酯溶液中的光解得到 1,2'-biazulene 衍生物，否则很难以良好的产率获得，近 90% 或更多。还表征了伴随的副产物 1,3-dicyanoazulen-6-ol 和 2,5'-biazulene 衍生物。
• Formation and structure of 2-diazo-2,4-azulenequinone derivatives
  作者：Tetsuo Nozoe、Toyonobu Asao、Masafumi Yasunami、Hisamitu Wakui、Toshio Suzuki、Masayoshi Ando

  DOI：10.1021/jo00123a031

  日期：1995.9

  The diazotization of methyl (and ethyl) 2-amino-3-cyano-4-methoxy(and ethoxy)azulene-1-carboxylate (1-4) was examined to determine whether the products are 2-diazo-2,4-azulenequinone derivatives (B) or azulene-2-diazonium-1-carboxylate derivatives (C). Since diazotization of 1 and 2 gave the same diazo compound 5 and diazotization of both 3 and 4-gave diazo compound 6, the diazo compounds are deduced to not be azulene-2-diazonium-1-carboxylate derivatives (7 and 8), but rather to be 2-diazo-2,4-azulenequinone derivatives (5 and 6). The diazo carbons of both 5 and 6 show C-13 NMR signals at delta 66.3, and their carbonyl carbons resonate at 6 181.1, in good agreement with a 2-diazo-2,4-azulenequinone structure. The structures of diazo compounds 24 and 25, which we have previously reported,(1) are reexamined on the basis of the analysis of their C-13 NMR spectra. The contribution of a quinoid structure and a diazoazulenolate structure to 5, 6, 24, and 25 is discussed by comparison of their C-13 NMR spectral data with those of 4-diazo-2,5-cyclohexadien-1-one derivatives. It is concluded that the contribution of the quinoid structure is larger than that of the diazoazulenolate structure.
• Wun, Wu-Che; Huang, Tian-Chyuan; Lin, Shih-Jue, Journal of the Chinese Chemical Society, 1993, vol. 40, # 6, p. 593 - 596
  作者：Wun, Wu-Che、Huang, Tian-Chyuan、Lin, Shih-Jue、Lin, Bing-Bing、Morita, Tadayoshi、Lin, Yun-Shan

  DOI：——

  日期：——