2-mercaptomethyl-5-methylthiophene | 136358-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-mercaptomethyl-5-methylthiophene
• 英文别名: 5-methyl-2-thenylthiol；(5-Methylthiophen-2-yl)methanethiol
• CAS: 136358-89-9
• 化学式: C₆H₈S₂
• 分子量: 144.262
• InChiKey: VAZXIFBACHWZIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  216.0±25.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)
• 保留指数：
  1183

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-mercaptomethyl-5-methylthiophene 在 二叔丁基过氧化物 、 potassium ethoxide 作用下， 以 乙醇 为溶剂， 生成 5-Methylthiophen-2-thioaldehyde anion radical
  参考文献：
  名称：

  Rotational conformers of furan- and thiophenethioaldehyde anion radicals

  摘要：

  The radical anions of the four isomeric furan and thiophene thioaldehydes have been obtained by photolysis, in an alkaline medium, of the corresponding thiols in the presence of di-tert-butyl peroxide. The same reaction also yields the four corresponding aldehyde radical anions, starting from the appropriate alcohols. The ESR spectra show that in most cases the two rotational conformers (E and Z) are present at the equilibrium. By means of appropriate methyl-substituted derivatives it has been possible to assign the structure of the two conformers. In the case of the 2-furan and 2-thiophene aldehyde anion radicals it has been also found that the conformational preference is the same as that exhibited by the corresponding molecules.

  DOI：

  10.1021/jo00022a023
• 作为产物：
  描述：

  (5-甲基噻吩-2-基)甲醇 在 盐酸 、 硫脲 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2-mercaptomethyl-5-methylthiophene
  参考文献：
  名称：

  通过改变关键咖啡气味呋喃-2-基甲硫醇的结构基序合成的巯基呋喃和巯基噻吩的同源系列中的结构-气味关联

  摘要：

  呋喃-2-基甲硫醇（2-糠硫醇； 2-FFT，1）是众所周知的烘烤和磨碎咖啡中的主要气味剂，先前还被广泛用于肉类，面包和烘焙等热处理食品中芝麻籽。其独特的咖啡香气质量非常低浓度引起，而事实上，呈现出类似的结构，只有极少数的化合物先前已在食品中描述使1结构-气味活性研究的合适人选。为了深入了解在低浓度下会发出类似咖啡的气味的结构特征，合成了46种杂环硫醇和硫醚，其中32种首次合成，并确定了它们的气味质量和气味阈值。巯基向3位的移动保持了咖啡样的香气，但是导致了气味阈值的增加。由于碳侧链的延长，硫醇基团与呋喃环的分离导致咖啡味气味的损失，并且还导致气味阈值的增加，尤其是对于ω-（呋喃-2-基）烷烃-在侧链中具有六个或七个碳原子的1-硫醇。呋喃环被噻吩环取代对大多数所研究化合物的气味特性没有显着影响，但是新合成的长链1-（呋喃-2-基）-和1-（噻吩-2-基）烷烃-1-硫醇引发了令人兴奋的百香果

  DOI：

  10.1021/acs.jafc.8b00857

文献信息

• [EN] 2 - (PYRIDIN- 2 -YL) -QUINAZOLINE DERIVATIVES AND THEIR USE AS MICROBICIDES<br/>[FR] DÉRIVÉS DE 2-(PYRIDIN-2-YL)-QUINAZOLINE ET LEUR UTILISATION EN TANT QUE MICROBICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2012066122A1

  公开（公告）日：2012-05-24

  Compounds of formula I wherein the other substituents R1, R2, R3, R4, R5 and R6 are as defined in claim 1, and their use as microbicides.

  式I中的化合物，其中其他取代基R1、R2、R3、R4、R5和R6如权利要求1所定义，并且它们作为微生物杀菌剂的用途。
• Mercaptomethylation of Aromatics
  作者：Tohru Nakamura、Mutsuyoshi Matsumoto

  DOI：10.1080/00397919908085758

  日期：1999.1

  Abstract Mercaptomethylarenes 2a - f were prepared in moderate yields by facile mercaptomethylation consisting of the metalation of the corresponding aromatics la - f with magnesium or butyllithium / magnesium bromide diethyl etherate, followed by the addition of 0-propyl chlorothioforrnate, and the reduction with lithium aluminum hydride or sodium borohydride.

  摘要 巯甲基芳烃 2a - f 是通过简单的巯基甲基化以中等产率制备的，该反应包括用镁或丁基锂 / 溴化镁二乙基醚化物金属化相应的芳烃 la - f，然后加入 0-丙基氯硫代甲酸酯，然后用锂铝还原氢化物或硼氢化钠。
• Identification of Potent Aroma Compounds in Thermally Treated Mixtures of Glucose/Cysteine and Rhamnose/Cysteine Using Aroma Extract Dilution Techniques
  作者：Thomas Hofmann、Peter Schieberle

  DOI：10.1021/jf960456t

  日期：1997.3.1

  Application of an aroma extract dilution analysis on extracts prepared from either thermally treated solutions (20 min, 145 degrees C) of glucose/cysteine (I) or rhamnose/cysteine (II) led to the identification of 2-furfurylthiol (roasty, coffee-like), 5-acetyl-2,3-dihydro-1,4-thiazine (roasty), 3-mercapto-2-butanone (sulfury, rotten), 3-mercapto-2-pentanone (catty), and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like) with the highest odor activities among the 34 odor-active volatiles detected in I. In II, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-hydroxy-6-methyl-2(2H)-pyranone (seasoning-like), 5-methyl-2-furfurylthiol (roasty, coffee-like), 2-furfurylthiol, and 5-acetyl-2,3-dihydro-1,4-thiazine appeared with the highest flavor dilution (FD) factors among the 18 compounds detected by HRGC/O. Among the flavor compounds identified, 2-propionyl-2-thiazoline is reported for the first time among the flavors of Maillard model reactions or foods, respectively. The odorant elicited an intense roasty, popcorn-like odor at the low odor threshold of 0.07 ng/L in air.
• [EN] INDOLE CARBOXAMIDES AS IKK2 INHIBITORS<br/>[FR] INDOLE CARBOXAMIDES EN TANT QU'INHIBITEURS D'IKK2
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2008118724A1

  公开（公告）日：2008-10-02

  [EN] The invention is directed to novel indole carboxamide compounds. Specifically, the invention is directed to compounds according to formula (I): wherein R1, R2, R3, R4, and m are as defined herein. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKß) activity, such as rheumatoid arthritis, asthma, rhinitis, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
  [FR] L'invention concerne de nouveaux composés d'indole carboxamide. L'invention concerne spécifiquement des composés de formule (I) : dans laquelle R1, R2, R3, R4 et m sont tels que définis dans le présent document. Les composés selon l'invention sont des inhibiteurs d'IKK2 et peuvent être utiles dans le traitement de troubles associés avec une activité inappropriée d'IKK2 (également connu sous le nom d'IKKß), par exemple la polyarthrite rhumatoïde, l'asthme, la rhinite et la BPCO (bronchopneumopathie chronique obstructive). L'invention concerne également des compositions pharmaceutiques qui comprennent un composé selon l'invention. L'invention concerne également des procédés d'inhibition de l'activité d'IKK2 et de traitement de troubles associés avec l'activité d'IKK2 qui utilisent un composé selon l'invention ou une composition pharmaceutique qui comprend un composé selon l'invention.
• Structure–Odor Correlations in Homologous Series of Mercapto Furans and Mercapto Thiophenes Synthesized by Changing the Structural Motifs of the Key Coffee Odorant Furan-2-ylmethanethiol
  作者：Sebastian Schoenauer、Peter Schieberle

  DOI：10.1021/acs.jafc.8b00857

  日期：2018.4.25

  seeds. Its unique coffee-like odor quality elicited at very low concentrations, and the fact that only a very few compounds showing a similar structure have previously been described in foods make 1 a suitable candidate for structure–odor activity studies. To gain insight into the structural features needed to evoke a coffee-like odor at low concentrations, 46 heterocyclic mercaptans and thio ethers

  呋喃-2-基甲硫醇（2-糠硫醇； 2-FFT，1）是众所周知的烘烤和磨碎咖啡中的主要气味剂，先前还被广泛用于肉类，面包和烘焙等热处理食品中芝麻籽。其独特的咖啡香气质量非常低浓度引起，而事实上，呈现出类似的结构，只有极少数的化合物先前已在食品中描述使1结构-气味活性研究的合适人选。为了深入了解在低浓度下会发出类似咖啡的气味的结构特征，合成了46种杂环硫醇和硫醚，其中32种首次合成，并确定了它们的气味质量和气味阈值。巯基向3位的移动保持了咖啡样的香气，但是导致了气味阈值的增加。由于碳侧链的延长，硫醇基团与呋喃环的分离导致咖啡味气味的损失，并且还导致气味阈值的增加，尤其是对于ω-（呋喃-2-基）烷烃-在侧链中具有六个或七个碳原子的1-硫醇。呋喃环被噻吩环取代对大多数所研究化合物的气味特性没有显着影响，但是新合成的长链1-（呋喃-2-基）-和1-（噻吩-2-基）烷烃-1-硫醇引发了令人兴奋的百香果