1,S,S-dimethyl-N-(4-nitroanthraquinon-1-yl)sulfoximide | 85193-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,S,S-dimethyl-N-(4-nitroanthraquinon-1-yl)sulfoximide
• 英文别名: 1-{[Dimethyl(oxido)-lambda~6~-sulfanylidene]amino}-4-nitroanthracene-9,10-dione；1-[[dimethyl(oxo)-λ6-sulfanylidene]amino]-4-nitroanthracene-9,10-dione
• CAS: 85193-00-6
• 化学式: C₁₆H₁₂N₂O₅S
• 分子量: 344.348
• InChiKey: ATJIEDMVKQXVDO-UHFFFAOYSA-N

物化性质

• 沸点：
  591.5±60.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,S,S-dimethyl-N-(4-nitroanthraquinon-1-yl)sulfoximide 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 5-(pyrrolidin-1-yl)naphtho[1,2,3-cd]indol-6(2H)-one
  参考文献：
  名称：

  Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones

  摘要：

  Heating of 6H-anthra[1,9-cd][1,2]oxazol-6-ones with dialkyl sulfoxides in sulfolane gave S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides which underwent cyclization to naphtho-[1,2,3-cd]indol-6(2H)-one derivatives on heating in boiling tetrahydrofuran in the presence of sodium methoxide. p-Toluenesulfinic acid was isolated as by-product in the cyclization of S-methyl-S-(4-methylphenyl)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximide. The heterocyclizations of S,S-dipropyl- and S,S-dibutyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides to 1-ethyl- and 1-propylnaphtho[1,2,3-cd]-indol-6(2H)-ones were accompanied by formation of the corresponding 1-[1-hydroxyethyl(propyl)]naphtho-[1,2,3-cd]indol-6(2H)-ones. DOI: 10.1134/S1070428013010132

  DOI：

  10.1134/s1070428013010132
• 作为产物：
  描述：

  1-azido-4-nitro-anthraquinone 以 甲苯 为溶剂， 反应 5.0h， 生成 1,S,S-dimethyl-N-(4-nitroanthraquinon-1-yl)sulfoximide
  参考文献：
  名称：

  Sutter, P.; Weis, C. D., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 997 - 1011

  摘要：

  DOI：

文献信息

• SUTTER, P.;WEIS, C. D., J. HETEROCYCL. CHEM., 1982, 19, N 5, 997-1011
  作者：SUTTER, P.、WEIS, C. D.

  DOI：——

  日期：——
• Sutter, P.; Weis, C. D., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 997 - 1011
  作者：Sutter, P.、Weis, C. D.

  DOI：——

  日期：——
• Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones
  作者：O. I. Kargina、L. M. Gornostaev、A. A. Nefedov

  DOI：10.1134/s1070428013010132

  日期：2013.1

  Heating of 6H-anthra[1,9-cd][1,2]oxazol-6-ones with dialkyl sulfoxides in sulfolane gave S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides which underwent cyclization to naphtho-[1,2,3-cd]indol-6(2H)-one derivatives on heating in boiling tetrahydrofuran in the presence of sodium methoxide. p-Toluenesulfinic acid was isolated as by-product in the cyclization of S-methyl-S-(4-methylphenyl)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximide. The heterocyclizations of S,S-dipropyl- and S,S-dibutyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides to 1-ethyl- and 1-propylnaphtho[1,2,3-cd]-indol-6(2H)-ones were accompanied by formation of the corresponding 1-[1-hydroxyethyl(propyl)]naphtho-[1,2,3-cd]indol-6(2H)-ones. DOI: 10.1134/S1070428013010132