ethyl 4-(2,3-dihydro-3-hydroperoxy-4,5-dimethyl-1,1-dioxoisothiazol-2-yl)benzoic acid | 433332-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(2,3-dihydro-3-hydroperoxy-4,5-dimethyl-1,1-dioxoisothiazol-2-yl)benzoic acid
• 英文别名: ethyl 4-(3-hydroperoxy-4,5-dimethyl-1,1-dioxo-3H-1,2-thiazol-2-yl)benzoate
• CAS: 433332-84-4
• 化学式: C₁₄H₁₇NO₆S
• 分子量: 327.358
• InChiKey: DZVBSLSFEPRYPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4-(2,3-dihydro-3-hydroperoxy-4,5-dimethyl-1,1-dioxoisothiazol-2-yl)benzoic acid 在 二甲基亚砜 作用下， 反应 2.0h， 以87%的产率得到ethyl 4-(2,3-dihydro-3-hydroxy-4,5-dimethyl-1,1-dioxoisothiazol-2-yl)benzoate
  参考文献：
  名称：

  Synthesis of Monocyclic Hydroperoxy- and Hydroxy-Substituted Sulfin- and Sulfonamides by Oxidation of 4,5-Dimethylisothiazolium Salts

  摘要：

  The isothiazolium salts 10, easily accessible by cyclocondensation of the thiocyanates 8 with the anilines 9, yielded with H,02 as the oxidant the first stable hydroperoxides of the 2-aryl-2,3-dihydroisothiazole 1-oxides rac-cis-13, the 1,1-dioxides 15, and their reduced 3-hydroxy derivatives rac-cis-14 and 16, respectively. The oxidation of 10 to new isothiazol-3(2H)-one 1,1-dioxides (17) is also described. For the first time, an aryl-bridged bis[isothiazolium salt] 11 was synthesized and oxidized.

  DOI：

  10.1002/1522-2675(200201)85:1<183::aid-hlca183>3.0.co;2-5
• 作为产物：
  描述：

  Z-2-Methyl-3-thiocyanatocrotonaldehyd 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 45.0h， 生成 ethyl 4-(2,3-dihydro-3-hydroperoxy-4,5-dimethyl-1,1-dioxoisothiazol-2-yl)benzoic acid
  参考文献：
  名称：

  Synthesis of Monocyclic Hydroperoxy- and Hydroxy-Substituted Sulfin- and Sulfonamides by Oxidation of 4,5-Dimethylisothiazolium Salts

  摘要：

  The isothiazolium salts 10, easily accessible by cyclocondensation of the thiocyanates 8 with the anilines 9, yielded with H,02 as the oxidant the first stable hydroperoxides of the 2-aryl-2,3-dihydroisothiazole 1-oxides rac-cis-13, the 1,1-dioxides 15, and their reduced 3-hydroxy derivatives rac-cis-14 and 16, respectively. The oxidation of 10 to new isothiazol-3(2H)-one 1,1-dioxides (17) is also described. For the first time, an aryl-bridged bis[isothiazolium salt] 11 was synthesized and oxidized.

  DOI：

  10.1002/1522-2675(200201)85:1<183::aid-hlca183>3.0.co;2-5

文献信息

• Thermochemiluminescence as a fast method to detect and characterize hydroperoxide moieties in novel 3-hydroperoxyisothiazole 1,1-dioxides
  作者：Matthias Gilbert、Valeria Zakharova、Anna Ramenda、Christian Jebsen、Bärbel Schulze、Christian Wilhelm

  DOI：10.1016/j.tet.2012.05.100

  日期：2012.8

  potential of these novel compounds is clearly linked to the hydroperoxide moiety. Hydroperoxides are known for their chemi- and thermochemiluminescent reactivity. In this study we tested thermochemiluminescence (TCL) as a fast method to detect and characterize the hydroperoxide moiety in structurally different synthetic organic hydroperoxides.

  氢过氧化合物对于化学工业中有机前体的选择性氧化非常重要。此外，新的3-氢过氧异噻唑1，1-二氧化物（N-邻苯二甲酰亚胺基）已被证明是有效的，乙酰胆碱酯酶（AChE）的特异性抑制剂是神经递质过程中的重要酶。这些新型化合物的抑制潜力显然与氢过氧化物部分有关。氢过氧化物因其化学和热化学发光反应性而闻名。在这项研究中，我们测试了热化学发光（TCL）作为检测和表征结构不同的合成有机氢过氧化物中氢过氧化物部分的快速方法。
• Synthesis of Monocyclic Hydroperoxy- and Hydroxy-Substituted Sulfin- and Sulfonamides by Oxidation of 4,5-Dimethylisothiazolium Salts
  作者：Kathleen Taubert、Joachim Sieler、Lothar Hennig、Matthias Findeisen、Bärbel Schulze

  DOI：10.1002/1522-2675(200201)85:1<183::aid-hlca183>3.0.co;2-5

  日期：2002.1

  The isothiazolium salts 10, easily accessible by cyclocondensation of the thiocyanates 8 with the anilines 9, yielded with H,02 as the oxidant the first stable hydroperoxides of the 2-aryl-2,3-dihydroisothiazole 1-oxides rac-cis-13, the 1,1-dioxides 15, and their reduced 3-hydroxy derivatives rac-cis-14 and 16, respectively. The oxidation of 10 to new isothiazol-3(2H)-one 1,1-dioxides (17) is also described. For the first time, an aryl-bridged bis[isothiazolium salt] 11 was synthesized and oxidized.