5-Chlor-2-ethyl-4-isothiazolin-3-on | 33344-74-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-Chlor-2-ethyl-4-isothiazolin-3-on
• 英文别名: 5-chloro-2-ethylisothiazol-3(2H)-one；5-chloro-2-ethyl-isothiazol-3-one；5-chloro-2-ethyl-3-isothiazolone；5-chloro-2-ethyl-4-isothiazoline-3-one；5-chloro-2-ethyl-1,2-thiazol-3-one
• CAS: 33344-74-0
• 化学式: C₅H₆ClNOS
• 分子量: 163.628
• InChiKey: MMONDPHQMXRZDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Chlor-2-ethyl-4-isothiazolin-3-on 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到5-chloro-2-ethylisothiazol-3(2H)-one-1-oxide
  参考文献：
  名称：

  Reactivity of isothiazolones and isothiazolone-1-oxides in the inhibition of the PCAF histone acetyltransferase

  摘要：

  Development of small molecule inhibitors of the histone acetyltransferase p300/CBP associated factor (PCAF) is relevant for oncology. The inhibition of the enzyme PCAF and proliferation of the cancer cell line HEP G2 by a series of 5-chloroisothiazolones was compared to a series of 5-chloroisothiazolone-1-oxides. The PCAF inhibitory potency of 5-chloroisothiazolones and 5-chloroisothiazolone-1-oxides is influenced by substitution in the 4-position. A study on the reactivity of the HAT inhibitors towards thiols and thiolates indicates that 5-chloroisothiazolones reacted quickly with propane-1-thiolate to provide many products, whereas 5-chloroisothiazolone-1-oxides provide only one defined product. Growth inhibition studies indicate that 5-chloroisothiazolones inhibit proliferation of HEP G2 cells at concentrations between 8.6 and 24 mu M, whereas 5-chloroisothiazolone-1-oxides required higher concentrations or showed no inhibition. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.07.025
• 作为产物：
  描述：

  3,3'-dithiobis(N-ethylpropanamide) 在 氯 作用下， 以 乙酸乙酯 为溶剂， 生成 5-Chlor-2-ethyl-4-isothiazolin-3-on
  参考文献：
  名称：

  Miller,G.A. et al., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 581 - 586

  摘要：

  DOI：

文献信息

• ANTIMICROBIAL AGENT FOR THE BIOCIDAL FINISH OF POLYMERS
  申请人：Wenatex Forschung - Entwicklung - Produktion GmbH

  公开号：US20170318813A1

  公开（公告）日：2017-11-09

  An antimicrobial agent for the biocidal finish of polymers based on biocides is described, whose molecules have at least one nitrogen atom with a free electron pair. In order to achieve an extensive insolubility without loss of the biocidal effect, it is proposed that the biocide is coordinatively bound to a metal complex via the free electron pair of the nitrogen atom.

  描述了一种用于基于生物杀菌剂的聚合物生物灭活整理的抗微生物剂，其分子至少具有一个带有自由电子对的氮原子。为了实现广泛的不溶性而不损失生物杀菌效果，建议通过氮原子的自由电子对将生物杀菌剂与金属配合物协同结合。
• Isothiazoles. Part 14: New 3-aminosubstituted isothiazole dioxides and their mono- and dihalogeno derivatives
  作者：Francesca Clerici、Alessandro Contini、Maria Luisa Gelmi、Donato Pocar

  DOI：10.1016/j.tet.2003.09.064

  日期：2003.11

  3-Alkylamino- and 3-arylamino isothiazole dioxides unsubstituted at C-4 and C-5 were synthesized starting from dithiopropionic amides. Taking advantage of the direct chlorination during the cyclization process or realizing an addition–elimination process with bromine on the final 3-aminoisothiazole dioxide derivatives, the corresponding 5-chloro-, 4,5-dichloro- or the 4-bromoisothiazole dioxides could

  由二硫代丙酰胺开始合成在C-4和C-5未取代的3-烷基氨基-和3-芳基氨基异噻唑二氧化物。利用环化过程中的直接氯化或在最终的3-氨基异噻唑二氧化物衍生物上用溴进行加成-消除过程，相应的5-氯-，4,5-二氯-或4-溴异噻唑也可能是提供。
• Halogen-free biocide
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0676140A1

  公开（公告）日：1995-10-11

  A synergistic biocide composition is disclosed comprising 2-methyl-3-isothiazolone and 2-n-octyl-3-isothiazolone which exhibits improved control against fungi and bacteria, the composition comprising less than 5% by weight of halogenated compounds, and preferably being halogen free.

  本发明公开了一种由 2-甲基-3-异噻唑啉酮和 2-正辛基-3-异噻唑啉酮组成的增效杀菌剂组合物，该组合物对真菌和细菌的控制能力更强，组合物中卤代化合物的含量小于 5%（按重量计），最好不含卤素。
• Stable biocidal compositions
  申请人：ROHM AND HAAS COMPANY

  公开号：EP1084619A1

  公开（公告）日：2001-03-21

  Disclosed are biocidal compositions comprising mixtures of formaldehyde-releasing imidazolidines, such as 1,3-dimethylol-5,5-dimethylhydantoin, and 3-isothiazolones stabilized with low levels of copper salts.

  所公开的杀菌组合物包含释放甲醛的咪唑烷类（如 1,3-二甲基-5,5-二甲基海因）和用低浓度铜盐稳定的 3-异噻唑啉酮的混合物。
• Stabilized microbicide formulation
  申请人：ROHM AND HAAS COMPANY

  公开号：EP1120040A2

  公开（公告）日：2001-08-01

  A method for stabilizing dilute solutions of 3-isothiazolone compounds against the formation of unwanted brown precipitate in the presence of low levels of copper, by the addition of 2 to 50% of selected water-soluble organic solvents, is disclosed. Preferably, the aqueous solutions are substantially free of metal nitrate, metal nitrite and magnesium salt stabilizers.

  本发明公开了一种稳定 3-异噻唑啉酮化合物稀溶液的方法，通过添加 2 至 50%的选定水溶性有机溶剂，可防止在铜含量较低时形成不需要的棕色沉淀。水溶液最好基本上不含金属硝酸盐、金属亚硝酸盐和镁盐稳定剂。