5-cyanotropolone | 3266-92-0

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 5-cyanotropolone
• 英文别名: 4-hydroxy-5-oxo-1,3,6-cycloheptatriene-1-carbonitrile；4-hydroxy-5-oxo-cyclohepta-1,3,6-trienecarbonitrile；4-Hydroxy-5-oxo-cyclohepta-1,3,6-triencarbonitril；4-hydroxy-5-oxocyclohepta-1,3,6-triene-1-carbonitrile
• CAS: 3266-92-0
• 化学式: C₈H₅NO₂
• 分子量: 147.133
• InChiKey: FUKXHWQWIFJSRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-cyanotropolone 在 氢氧化钾 作用下， 生成 5-carboxytropolone
  参考文献：
  名称：

  Cook et al., Journal of the Chemical Society, 1954, p. 530,533

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 5-cyanotropolone
  参考文献：
  名称：

  Kitahara, Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., 1956, vol. 40, p. 83,86

  摘要：

  DOI：

文献信息

• The Reaction of Tropolones with Phosphorus Oxychloride. The Rearrangement Reaction of 5-Arylazo-2-chlorotropones to 2-Aryl-4, 5-dichloroindazoles
  作者：Katsuo Kikuchi、Masaki Yagi、Kunio Takada

  DOI：10.1246/bcsj.41.424

  日期：1968.2

  The reaction of tropolone and phosphorus oxychloride gave 2-chlorotropone. Similarly, 5-cyano-, 5-nitro, and 5-chlorotropolones afforded the corresponding 2-chlorotropone derivatives in moderate yields. 3-Cyanotropolone gave 2-chloro-7-cyanotropone, while 3-phenyltropolone afforded only 2-chloro-3-phenylbenzaldehyde. When 3-bromotropolone and 5-bromotropolone were treated similarly, 2, 7-dichloro- and 2, 5-dichlorotropones were obtained respectively, with a facile halogen exchange. The further treatment of 2, 5-dichlorotropone with phosphorus oxychloride afforded 2, 5-dichloro- and 3,4-dichlorobenzaldehydes. The reaction of 5-p-tolylazo-, 5-phenylazo-, and 5-p-nitrophenylazotropolones with phosphorus oxychloride gave the corresponding 5-arylazo-2-chlorotropones, which, on further treatment with an excess of the reagent, gave 2-aryl-4, 5-dichloroindazoles.

  倍氯酮与磷氧氯化物的反应生成了2-氯倍酮。同样，5-氰基、5-硝基和5-氯倍氯酮也分别获得了相应的2-氯倍酮衍生物，产率适中。3-氰基倍氯酮生成了2-氯-7-氰基倍酮，而3-苯基倍氯酮则仅获得了2-氯-3-苯基苯甲醛。当3-溴倍氯酮和5-溴倍氯酮以类似方式处理时，分别得到2,7-二氯和2,5-二氯倍酮，伴随简单的卤素交换。进一步用磷氧氯化物处理2,5-二氯倍酮，得到2,5-二氯和3,4-二氯苯甲醛。5-p-苯基偶氮、5-苯基偶氮和5-p-硝基苯基偶氮倍酮与磷氧氯化物的反应生成了相应的5-芳基偶氮-2-氯倍酮，经过进一步处理后与过量的试剂反应，得到2-芳基-4,5-二氯吲唑。
• The Rearrangement of Tropones to Dihydrobenzene Derivatives
  作者：Katsuo Kikuchi

  DOI：10.1246/bcsj.40.355

  日期：1967.2

  The positions of the double bonds in 1-phenylcyclohexadiene-1,2-dicarboxylic acid, which had been obtained previously by the alkaline rearrangement of 2-phenyltropone-7-carboxylic acid, were elucidated from the spectral data. A similar rearrangement of tropone derivatives to dihydrobenzene derivatives was also observed. Tropone-2-carboxylic acid gave 2,5-cyclohexadiene-1,2-dicarboxylic acid, while 2-phenyltropone-5-carboxylic acid afforded 1-phenyl-2,4-cyclohexadiene-1,4-dicarboxylic acid. 2-Phenyltropone was also rearranged by alkali to 2-phenyl-2,5-cyclohexadiene-1-carboxylic acid.

  光谱数据阐明了 1-苯基环己二烯-1,2-二羧酸中双键的位置，该双键是之前通过 2-苯基托品酮-7-羧酸的碱性重排得到的。还观察到托品酮衍生物与二氢苯衍生物发生了类似的重排反应。托品酮-2-羧酸可生成 2,5-环己二烯-1,2-二羧酸，而 2-苯基托品酮-5-羧酸可生成 1-苯基-2,4-环己二烯-1,4-二羧酸。2-phenyltropone 还能通过碱重新排列为 2-苯基-2,5-环己二烯-1-羧酸。
• Liquid Crystals with a 5-Cyanotropone Skeleton: 2-(4-Alkoxybenzoyloxy)-5-cyanotropone and 2-(4-Alkoxybenzoylamino)-5-cyanotropones
  作者：Masashi Hashimoto、Seiji Ujiie、Akira Mori

  DOI：10.1246/cl.2000.758

  日期：2000.7

  New troponoid liquid crystals with an electron-withdrawing cyano group at the C-5 position of tropolone and 2-aminotropone rings were prepared. Tropolone derivatives had nematic phases with lower thermal stabilities and smectic A phases with higher thermal stabilities than the corresponding benzenoids while thermal stabilities of the aminotropone derivatives were better than those of the benzenoids

  制备了在托酚酮的 C-5 位具有吸电子氰基的新型 troponoid 液晶和 2-aminotropone 环。托酚酮衍生物的向列相具有较低的热稳定性和近晶相 A 相的热稳定性高于相应的苯类化合物，而氨基托酮衍生物的热稳定性优于苯类化合物的热稳定性。X 射线衍射研究表明，在近晶 A 相中测得的层间距与计算的分子长度之比对于托酚酮衍生物为 1.3，对于氨基托酚酮衍生物为 1.45。他们形成了交叉的双层。
• PHOTOBASE GENERATOR AND PHOTOCURABLE RESIN COMPOSITION
  申请人：Asahi Kasei Chemicals Corporation

  公开号：EP2093269A1

  公开（公告）日：2009-08-26

  Disclosed is a photobase generator comprising a compound having a nitrogen atom and a conjugated multiple bond.

  本发明公开了一种光碱发生器，它包含一种具有氮原子和共轭多键的化合物。
• US8137892B2
  申请人：——

  公开号：US8137892B2

  公开（公告）日：2012-03-20

表征谱图