1-[1,4-dioxo-3-(toluene-4-sulfonylamino)-1,4-dihydro-[2]naphthyl]-pyridinium betaine | 166902-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[1,4-dioxo-3-(toluene-4-sulfonylamino)-1,4-dihydro-[2]naphthyl]-pyridinium betaine
• 英文别名: 1-[1,4-Dioxo-3-(toluol-4-sulfonylamino)-1,4-dihydro-[2]naphthyl]-pyridinium-betain；[1,4-Dioxo-3-(pyridinium-1-yl)-1,4-dihydronaphthalen-2-yl][(4-methylphenyl)sulfonyl]azanide；(3Z)-3-(4-methylphenyl)sulfonylimino-4-oxo-2-pyridin-1-ium-1-ylnaphthalen-1-olate
• CAS: 166902-16-5
• 化学式: C₂₂H₁₆N₂O₄S
• 分子量: 404.446
• InChiKey: QVWURLONKTXWHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  98.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[1,4-dioxo-3-(toluene-4-sulfonylamino)-1,4-dihydro-[2]naphthyl]-pyridinium betaine 在 吡啶 、 氯化亚砜 、 sulfinylcarbamic acid ethyl ester 作用下， 以 苯 为溶剂， 反应 2.0h， 以68%的产率得到naphtho<2,3-c><1,2,5>thiadiazole-4,9-dione
  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：

  1,4-二羟基萘 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 1-[1,4-dioxo-3-(toluene-4-sulfonylamino)-1,4-dihydro-[2]naphthyl]-pyridinium betaine
  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

文献信息

• Ullmann; Ettisch, Chemische Berichte, 1921, vol. 54, p. 271
  作者：Ullmann、Ettisch

  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.