1-(3,4-dimethyl-2-thioxo-2,3-dihydrothiazol-5-yl)ethanone | 252010-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,4-dimethyl-2-thioxo-2,3-dihydrothiazol-5-yl)ethanone
• 英文别名: 1-(2,3-dihydro-3,4-dimethyl-2-thioxothiazol-5-yl)-1-ethanone；1-(3,4-Dimethyl-2-thioxo-2,3-dihydro-1,3-thiazol-5-yl)ethanone；1-(3,4-dimethyl-2-sulfanylidene-1,3-thiazol-5-yl)ethanone
• CAS: 252010-03-0
• 化学式: C₇H₉NOS₂
• mdl: MFCD03502173
• 分子量: 187.287
• InChiKey: PEBZNWZQGFTIPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethyl-2-thioxo-2,3-dihydrothiazol-5-yl)ethanone 在 selenium 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 亚磷酸三乙酯 作用下， 以 乙醇 、 氯仿 、 甲苯 、 乙腈 为溶剂， 反应 13.5h， 生成 1-[(2E)-2-(5-acetyl-3,4-dimethyl-1,3-thiazol-2-ylidene)-3,4-dimethyl-1,3-thiazol-5-yl]ethanone
  参考文献：
  名称：

  Chemical and Electrochemical Investigations on Thiazolium Salts: a Route to Powerful Donors in the Dithiadiazafulvalene Series.

  摘要：

  Thiazolium salts have been investigated, chemically and electrochemically, in order to access to the redox properties of dithiadiazafulvalenes (DTDAF). As these donor molecules are oxygen-sensitive, it is more advisable to isolate them in their oxidized form as dicationic salts. Starting from a tetrathiazolium cation including two precursors groups, linked together with a conjugated spacer, a bis-DTDAF was formed and its electrochemical behavior studied.

  DOI：

  10.3891/acta.chem.scand.53-0861
• 作为产物：
  描述：

  2,4-dioxopentan-3-yl N-methylcarbamodithioate 以 苯 为溶剂， 反应 3.0h， 以1.5 g的产率得到1-(3,4-dimethyl-2-thioxo-2,3-dihydrothiazol-5-yl)ethanone
  参考文献：
  名称：

  3,4-二烷基-5-（1-氧代乙基）-3H-噻唑-2-硫酮衍生物的合成及其杀虫活性

  摘要：

  通过N-甲基（乙基）-二硫代氨基甲酸钠盐与3-氯-戊烷-2,4-dion的相互作用，生成1-（3-烷基-4-甲基-2-硫代2-2,3-二氢噻唑-5基）-ethanones 1，2和相应的肟7，8合成。上所提到的化合物的基础亚肼（3，4），和ureayl thioureayl（5，6）的衍生物，取代的肟（9，10）和吖嗪基肟（11，12）。通过质子核磁共振波谱和元素分析证实了合成化合物的结构。研究了合成化合物的杀虫活性。一些合成的化合物同时显示出生长刺激和杀真菌活性。

  DOI：

  10.1002/jhet.1596

文献信息

• Heterocyclic thiones and their analogs in 1,3-dipolar cycloaddition: VII. Reaction of 4-methyl-1,3-thiazole-2(3H)-thiones with nitrile imines
  作者：E. V. Budarina、T. S. Dolgushina、M. L. Petrov、N. N. Labeish、A. A. Kol’tsov、V. K. Bel’skii

  DOI：10.1134/s1070428007100193

  日期：2007.10

  Reactions of 4-methyl-1,3-thiazole-2(3H)-thiones with various C,N-disubstituted nitrile imines occurred by the common [3+2]-cycloaddition scheme leading to the formation in general of stable spiro compounds. In reactions of o-nitrophenylnitrile imines acyclic compounds were the main products.
• A one-pot synthesis of N-alkylthiazoline-2-thiones from CS2, primary amines, and 2-chloro-1,3-dicarbonyl compounds in water
  作者：Issa Yavari、Mehdi Sirouspour、Sanaz Souri

  DOI：10.1007/s00706-009-0227-2

  日期：2010.1

  A simple synthesis of N-alkylthiazoline-2-thiones by reaction of primary amines, carbon disulfide, and 2-chloro-1,3-dicarbonyl compounds in water is described. Proceeding without catalyst under one-pot conditions in high yields and with broad scope, this method high synthetic utility.
• Chemical and Electrochemical Investigations on Thiazolium Salts: a Route to Powerful Donors in the Dithiadiazafulvalene Series.
  作者：Nathalie Bellec、David Guérin、Dominique Lorcy、Albert Robert、Roger Carlier、André Tallec、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0861

  日期：——

  Thiazolium salts have been investigated, chemically and electrochemically, in order to access to the redox properties of dithiadiazafulvalenes (DTDAF). As these donor molecules are oxygen-sensitive, it is more advisable to isolate them in their oxidized form as dicationic salts. Starting from a tetrathiazolium cation including two precursors groups, linked together with a conjugated spacer, a bis-DTDAF was formed and its electrochemical behavior studied.
• Synthesis of 3,4-Dialkyl-5-(1-oxo-ethyl)-3<i>H</i>-thiazole-2-thiones Derivatives and Their Pesticidal Activity
  作者：Karine A. Eliazyan、Aram M. Knyazyan、Vergush A. Pivazyan、Emma A. Ghazaryan、Siranush V. Harutyunyan、Aleksandr P. Yengoyan

  DOI：10.1002/jhet.1596

  日期：2013.7

  thioureayl (5, 6) derivatives, substituted oximes (9, 10) and azinyl oximes (11, 12) were obtained. The structures of synthesized compounds were confirmed by proton nuclear magnetic resonance spectroscopy and elemental analysis. The pesticidal activities of synthesized compounds were studied. Some of the synthesized compounds simultaneously have shown growth stimulant and fungicidal activity.

  通过N-甲基（乙基）-二硫代氨基甲酸钠盐与3-氯-戊烷-2,4-dion的相互作用，生成1-（3-烷基-4-甲基-2-硫代2-2,3-二氢噻唑-5基）-ethanones 1，2和相应的肟7，8合成。上所提到的化合物的基础亚肼（3，4），和ureayl thioureayl（5，6）的衍生物，取代的肟（9，10）和吖嗪基肟（11，12）。通过质子核磁共振波谱和元素分析证实了合成化合物的结构。研究了合成化合物的杀虫活性。一些合成的化合物同时显示出生长刺激和杀真菌活性。