3-甲基-4-硝基-1,2-噻唑-5-胺 | 40184-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-甲基-4-硝基-1,2-噻唑-5-胺
• 英文名称: 5-amino-3-methyl-4-nitroisothiazole
• 英文别名: 3-methyl-4-nitro-isothiazol-5-ylamine；3-Methyl-4-nitro-isothiazol-5-ylamin；5-Amino-3-methyl-4-nitroisothiazol (III)；3-Methyl-4-nitro-1,2-thiazol-5-amine
• CAS: 40184-32-5
• 化学式: C₄H₅N₃O₂S
• mdl: MFCD18821783
• 分子量: 159.169
• InChiKey: PYRFGRMRABTCCV-UHFFFAOYSA-N

物化性质

• 熔点：
  176-179 °C
• 沸点：
  193.5±40.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-甲基-4-硝基-1,2-噻唑-5-胺 在 磷酸 、 硝酸 、 sodium nitrite 作用下， 生成 5-溴-3-甲基-4-硝基-1,2-噻唑
  参考文献：
  名称：

  613.异噻唑：一种新的单核杂环系统

  摘要：

  DOI：

  10.1039/jr9590003061
• 作为产物：
  描述：

  5-Dichloracetamido-3-methyl-4-nitro-isothiazol 在 盐酸 作用下， 生成 3-甲基-4-硝基-1,2-噻唑-5-胺
  参考文献：
  名称：

  613.异噻唑：一种新的单核杂环系统

  摘要：

  DOI：

  10.1039/jr9590003061

文献信息

• Isothiazoles. Part XIV. 5-Alkoxy- and 5-hydroxyisothiazoles
  作者：I. D. H. Stocks、J. A. Waite、K. R. H. Wooldridge

  DOI：10.1039/j39710001314

  日期：——

  5-Bromoisothiazoles are attacked by nucleophiles to give 5-alkoxy- and (the hitherto unknown) 5-hydroxy-iso-thiazoles. 4-Bromo-5-hydroxy-3-methylisothiazole has been prepared by hydrolytic decomposition of the appropriate 5-diazonium fluoroborate. Preliminary studies on the tautomeric state of the hydroxyisothiazoles are reported.

  5-溴异噻唑被亲核试剂攻击，生成5-烷氧基-和（迄今未知）5-羟基-异噻唑。通过适当的氟硼酸5-重氮鎓的水解分解制备了4-溴-5-羟基-3-甲基异噻唑。报道了对羟基异噻唑的互变异构状态的初步研究。
• The synthesis of some 4-nitroisothiazoles as potential antifungal agents
  作者：Anthony H. Albert、Darrell E. O'Brien、Roland K. Robins

  DOI：10.1002/jhet.5570170235

  日期：1980.3

  5-Chloro-3-methyl-4-nitroisothiazole (III) was prepared by nitration of 5-chloro-3-methyliso-thiazole. Compound III was found to exhibit significant antifungal activity in vitro against a wide spectrum of fungi. The synthesis of 3-methyl-4-nitro-5-nitroamino, 5-carboxamido, 5-N,N-dimethylamino and 5-β-hydroxyethylaminoisothiazole are here reported. The synthesis of 3-methyl-4-nitroso-5-ethylthioisothiazole

  通过将5-氯-3-甲基异噻唑硝化制备5-氯-3-甲基-4-硝基异噻唑（III）。发现化合物III在体外对广谱真菌表现出显着的抗真菌活性。这里报道了3-甲基-4-硝基-5-硝基氨基，5-甲酰胺基，5- N，N-二甲基氨基和5-β-羟乙基氨基异噻唑的合成。通过5-溴-3-甲基-4-硝基异噻唑（I）与乙基硫醇钠的不寻常反应，报道了3-甲基-4-亚硝基-5-乙基硫代异噻唑（IX）的合成。通过将5-溴异噻唑硝化制备5-溴-4-硝基异噻唑。已证明硝基对于抗真菌活性是必不可少的。
• The synthesis of several imidazo[4,5-<i>d</i>]isothiazoles. Derivatives of a new ring system
  作者：Eric E. Swayze、Leroy B. Townsend

  DOI：10.1002/jhet.5570300533

  日期：1993.10

  the new imidazo[4,5-d]isothiazole ring system have been synthesized from the appropriately substituted isothiazolediamines. The reaction of 3-methyl-4,5-diaminoisothiazole (4a) with diethoxy-methyl acetate gave a low yield of 3-methylimidazo[4,5-d]isothiazole (5a). However, the analogous reaction of 4,5-diaminoisothiazole (4b) with diethoxymethyl acetate failed to yield the parent imidazo[4,5-d]isothiazole

  从适当取代的异噻唑二胺合成了新的咪唑并[4,5- d ]异噻唑环系的几种衍生物。3-甲基-4,5-二氨基异噻唑（4a）与二乙氧基乙酸甲酯的反应产生了低产率的3-甲基咪唑并[4,5- d ]异噻唑（5a）。然而，4，5-二氨基异噻唑（4b）与二乙氧基甲基乙酸酯的类似反应未能产生母体咪唑并[4，5- d ]异噻唑环系统。二胺4a和4b易于与硫代羰基二咪唑环合，得到不稳定的硫酮6a和6b，它们被烷基化了原位得到相应的5-甲基硫代咪唑并[4，5- d ]异噻唑7a和7b的良好产率。通过用阮内镍处理，这些化合物都不能还原为相应的5-未取代的衍生物。据我们所知，这是咪唑并[4,5- d ]异噻唑环系统的首次报道。
• [EN] ANTICANCER COMPOUNDS<br/>[FR] COMPOSES ANTICANCER
  申请人：PLANTACEUTICA INC

  公开号：WO2004033423A3

  公开（公告）日：2004-07-29
• The Synthesis of Substituted Imidazo[4,5-d]isothiazoles via the Ring Annulation of Isothiazole Diamines: An Investigation of the Chemical, Physical, and Biological Properties of Several Novel 5:5 Fused Analogs of the Purine Ring System
  作者：Eric E. Swayze、Leroy B. Townsend

  DOI：10.1021/jo00125a016

  日期：1995.10

  A series of imidazo[4,5-d]isothiazoles have been prepared from isothiazole precursors via a strategy employing ring annulation of the appropriate isothiazole diamine. In this manner, several 4,5-diaminoisothiazoles were converted into the corresponding 5-(alkylthio)imidazo[4,5-d]isothiazoles via a two-step, one-pot procedure in good yield. This methodology proved quite general and allows for the introduction of various substituents onto the 3-, 5-, and 6-positions of this ring system. Reaction with Raney nickel destroyed the ring system, presumably through removal of the sulfur at the 1-position, and the 5-mercapto substituent could not be removed selectively. Ring annulation with diethoxymethyl acetate provided the 5-unsubstituted imidazo[4,5-d]isothiazoles but was less general, and only the 3-methyl derivatives could be prepared. Imidazo[4,5-d]isothiazoles bearing no substituents on nitrogen readily underwent alkylation to afford mixtures of the N-4- and N-6-substituted compounds. The chemical and physical properties of these novel heterocycles were studied in detail, and the structure of 3-methyl-5-methanesulfonyl-6-(phenylmethyl)imidazo[4,5-d] isothiazole was verified by single crystal X-ray diffraction studies.