Anthra[2,3-d]thiazole-5,10-dione, 9-(acetyloxy)-

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Anthra[2,3-d]thiazole-5,10-dione, 9-(acetyloxy)-
• 英文别名: (5,10-dioxonaphtho[6,7-f][1,3]benzothiazol-9-yl) acetate
• 化学式: C₁₇H₉NO₄S
• 分子量: 323.329
• InChiKey: HPJWEAJLGPADGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-acetoxy-3-bromo-1,4-naphthoquinone 、 4-(bromomethyl)-5-(dibromomethyl)-1,3-thiazole 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Anthra[2,3-d]thiazole-5,10-dione, 9-(acetyloxy)- 、 (5,10-Dioxonaphtho[7,6-f][1,3]benzothiazol-6-yl) acetate
  参考文献：
  名称：

  Generation and Trapping of 4-Methylene-5-(bromomethylene)-4,5-dihydrothiazole with Dienophiles

  摘要：

  4-(Bromomethyl)-5-(dibromomethyl)thiazole (1) was prepared in good yields by bromination of 4,5-dimethylthiazole with 3.3 equiv of NBS in the presence of AIBN. Treatment of 1 with sodium iodide led to a thiazole o-quinodimethane 2 which was trapped in situ with dienophiles such as N-phenylmaleimide, DMAD, or acrylate derivatives. From the latter, 6-substituted-4,5-dihydrobenzothiazoles 7 are selectively formed. Anthra[2,3-b]thiazole-4,5-diones 13-15 were obtained from naphthoquinones. With 2- or 3-bromonaphthoquinones (11 or 12), the cycloadditions were found highly regioselective. Structural assignment of the regioisomers was made by a 2D H-1-C-13 HMBC technique performed on the aromatized cycloadduct 15b. Calculations of HOMO and LUMO frontier orbital coefficients by the semiempirical PM3 method show that the regiochemistry observed in the cycloadditions of 2 toward acrylate dienophiles or naphthoquinones 11 and 12 did not agree with the corresponding values.

  DOI：

  10.1021/jo961457n

文献信息

• Generation and Trapping of 4-Methylene-5-(bromomethylene)-4,5-dihydrothiazole with Dienophiles
  作者：Mouaffak Al Hariri、Karine Jouve、Félix Pautet、Monique Domard、Bernard Fenet、Houda Fillion

  DOI：10.1021/jo961457n

  日期：1997.1.1

  4-(Bromomethyl)-5-(dibromomethyl)thiazole (1) was prepared in good yields by bromination of 4,5-dimethylthiazole with 3.3 equiv of NBS in the presence of AIBN. Treatment of 1 with sodium iodide led to a thiazole o-quinodimethane 2 which was trapped in situ with dienophiles such as N-phenylmaleimide, DMAD, or acrylate derivatives. From the latter, 6-substituted-4,5-dihydrobenzothiazoles 7 are selectively formed. Anthra[2,3-b]thiazole-4,5-diones 13-15 were obtained from naphthoquinones. With 2- or 3-bromonaphthoquinones (11 or 12), the cycloadditions were found highly regioselective. Structural assignment of the regioisomers was made by a 2D H-1-C-13 HMBC technique performed on the aromatized cycloadduct 15b. Calculations of HOMO and LUMO frontier orbital coefficients by the semiempirical PM3 method show that the regiochemistry observed in the cycloadditions of 2 toward acrylate dienophiles or naphthoquinones 11 and 12 did not agree with the corresponding values.

表征谱图