6-cyano-1,4-naphthoquinone | 88437-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-cyano-1,4-naphthoquinone
• 英文别名: 5,8-dioxo-5,8-dihydro-[2]naphthonitrile；2-Naphthalenecarbonitrile, 5,8-dihydro-5,8-dioxo-；5,8-dioxonaphthalene-2-carbonitrile
• CAS: 88437-16-5
• 化学式: C₁₁H₅NO₂
• 分子量: 183.166
• InChiKey: KHUFLWSKTBKCAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 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：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-cyano-1,4-naphthoquinone 在 吡啶 、 氯化亚砜 、 氨基甲酸甲酯 作用下， 以 苯 为溶剂， 反应 12.0h， 以82%的产率得到4,9-Dioxo-4,9-dihydro-2-thia-1,3-diaza-cyclopenta[b]naphthalene-6-carbonitrile
  参考文献：
  名称：

  Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them

  摘要：

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.

  DOI：

  10.1021/jo00110a036
• 作为产物：
  描述：

  2,3-双(2-氰乙基)-1,4-二甲氧基苯 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 ammonium cerium(IV) nitrate 、 偶氮二异丁腈 、 sodium hydride 、 三乙胺 作用下， 反应 3.5h， 生成 6-cyano-1,4-naphthoquinone
  参考文献：
  名称：

  Furuichi, Kimiaki; Tada, Hitoshi; Itoh, Akira, Journal of the Chemical Society. Perkin transactions II, 1994, # 6, p. 1363 - 1378

  摘要：

  DOI：

文献信息

• Tanaka, Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1957, vol. 60, p. 1512
  作者：Tanaka

  DOI：——

  日期：——
• Furuichi, Kimiaki; Tada, Hitoshi; Itoh, Akira, Journal of the Chemical Society. Perkin transactions II, 1994, # 6, p. 1363 - 1378
  作者：Furuichi, Kimiaki、Tada, Hitoshi、Itoh, Akira、Takeuchi, Yasuyo、Mitoori, Masashi、et al.

  DOI：——

  日期：——
• Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them
  作者：Shuhao Shi、Thomas J. Katz、Bingwei V. Yang、Longbin Liu

  DOI：10.1021/jo00110a036

  日期：1995.3

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.