2,5-Bis(2-butoxyethoxy)[1,2,5]thiadiazolo[3'',4'':6',7']naphtho[1',2':5,6]phenanthro[2,3-C][1,2,5]thiadiazole-7,11,12,16-tetrone

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,5-Bis(2-butoxyethoxy)[1,2,5]thiadiazolo[3'',4'':6',7']naphtho[1',2':5,6]phenanthro[2,3-C][1,2,5]thiadiazole-7,11,12,16-tetrone
• 英文别名: 13,18-bis(2-butoxyethoxy)-7,24-dithia-6,8,23,25-tetrazaheptacyclo[15.11.0.02,14.03,11.05,9.020,28.022,26]octacosa-1(28),2,5,8,11,13,15,17,19,22,25-undecaene-4,10,21,27-tetrone
• 化学式: C₃₄H₃₀N₄O₈S₂
• 分子量: 686.766
• InChiKey: YGSMUPCKXFCVTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  213
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1,4,10,13-tetrahydro-1,4,10,13-tetraoxo-6,9-bis(2-butoxyethoxy)[5]helicene 在 吡啶 、 氯化亚砜 、 氨基甲酸甲酯 作用下， 以 苯 为溶剂， 反应 16.0h， 以43%的产率得到2,5-Bis(2-butoxyethoxy)[1,2,5]thiadiazolo[3'',4'':6',7']naphtho[1',2':5,6]phenanthro[2,3-C][1,2,5]thiadiazole-7,11,12,16-tetrone
  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

• 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.