2-methylmercapto-4-phenylthiazole | 2103-86-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methylmercapto-4-phenylthiazole
• 英文别名: 2-(methylthio)-4-phenylthiazole；2-methylsulfanyl-4-phenyl-thiazole；2-Methylmercapto-4-phenyl-thiazol；2-methylthio-4-phenyl-thiazole；4-Phenyl-2-methylmercapto-thiazol；2-Methylmercapto-4-phenylthiazol；2-methylsulfanyl-4-phenyl-1,3-thiazole
• CAS: 2103-86-8
• 化学式: C₁₀H₉NS₂
• 分子量: 207.32
• InChiKey: UCLTXHQWNOTMBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methylmercapto-4-phenylthiazole 在 triethylamine pentahydrogen fluoride salt 作用下， 以 乙二醇二甲醚 、 正己烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 5,5-difluoro-2-hydroxy-2-methylthio-4-phenyl-2,5-dihydrothiazole
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 64.¹ Anodic Mono- and Difluorination of Thiazolyl Sulfides

  摘要：

  The anodic fluorination of 2-thiazolyl methyl sulfide, 2-thiazolyl propargyl sulfide, and 2-thiazolyl acetonyl sulfide was successfully carried out to provide the corresponding 5-fluorothiazole and 2,5,5-trifluorothiazoline derivatives. The latter products were readily hydrolyzed to give isolable 5,5-difluoro-2-hydroxythiazoline derivatives. On the other hand, anodic fluorination of 2-thiazolyl cyanomethyl sulfide afforded 5-fluorothiazole and a-fluorinated thiazole derivatives. Thus, the product selectivity was found to be greatly changed by the electron-withdrawing ability of substituents at the side chain of the thiazole ring. This is the first report of a successful anodic fluorination of a thiazole ring.

  DOI：

  10.1021/jo020411t
• 作为产物：
  描述：

  2-巯基-4-苯基噻唑 在 potassium cyanide 、 乙醇 、 碘 作用下， 生成 2-methylmercapto-4-phenylthiazole
  参考文献：
  名称：

  Levi, Gazzetta Chimica Italiana, 1931, vol. 61, p. 719,726

  摘要：

  DOI：

文献信息

• 2-[3H-THIAZOL-2-YLIDINEMETHYL]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE
  申请人：Brown Robert

  公开号：US20090247579A1

  公开（公告）日：2009-10-01

  The present invention pertains to certain 2-[3H-thiazol-2-ylidinemethyl]pyridine compounds and analogs thereof, which, inter alia, inhibit cell proliferation, treat cancer, etc., and more specifically to compounds of the following formula, wherein R A1 , R A2 , R A3 , R A4 , R B1 , R B2 , R NA , R NB , and X − are as defined herein: The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit cell proliferation, and in the treatment of proliferative conditions such as cancer, etc.

  本发明涉及某些2-[3H-噻唑-2-基亚甲基]吡啶化合物及其类似物，其中包括抑制细胞增殖、治疗癌症等作用，更具体地涉及以下式的化合物，其中R A1 、R A2 、R A3 、R A4 、R B1 、R B2 、R NA 、R NB 和X − 如本文所定义： 本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制细胞增殖，并用于治疗癌症等增生性疾病。
• Cycloaddition Reactions of Thiazolium Azomethine Ylides:  Application to Pyrrolo[2,1-<i>b</i>]thiazoles
  作者：Craig R. Berry、Craig A. Zificsak、Alan C. Gibbs、Dennis J. Hlasta

  DOI：10.1021/ol071229n

  日期：2007.10.1

  Thiazolium azomethine ylides, equipped with a C-2 methanethiol group, participate in an efficient [3 + 2] cycloaddition reaction with acetylene derivatives to yield unique pyrrolo[2,1-b]thiazoles. The elimination of the methanethiol leaving group from the cycloadduct has replaced the need for a separate oxidation step and suppresses ring-opening side reactions. Products were obtained in short synthetic

  配备有C-2甲硫醇基的噻唑鎓甲亚胺基化物与乙炔衍生物一起参与有效的[3 + 2]环加成反应，从而生成独特的吡咯并[2,1-b]噻唑。从环加合物中消除甲硫醇离去基团取代了对单独氧化步骤的需要，并抑制了开环副反应。以短合成顺序获得产物，以证明其用作化合物文库的支架。
• S-Alkylation en s�rie h�t�rocyclique par catalyse par transfert de phase: thioalkyl-2-thiazoles, thioalkyl-2-?-4-thiazolines et thioalkyl-2-benzothiazoles
  作者：Henri J. M. Dou、Parina Hassanaly、Jacky Kister、Gaston Vernin、Jacques Metzger

  DOI：10.1002/hlca.19780610842

  日期：1978.12.13

  S-Alkylation in heterocyclic serie by phase transfer catalysis: 2-alkylthiothiazoles, 2-alkylthio-Δ-4-thiazolines and 2-alkylthiobenzothiazoles

  相转移催化在杂环系列中的S-烷基化：2-烷硫基噻唑，2-烷硫基-Δ-4-噻唑啉和2-烷硫基苯并噻唑
• Palladium-Catalyzed Regio- and Stereoselective Carbothiolation of Terminal Alkynes with Azolyl Sulfides
  作者：Masayuki Iwasaki、Nikola Topolovčan、Hao Hu、Yugo Nishimura、Glwadys Gagnot、Rungsaeng Na nakorn、Ramida Yuvacharaskul、Kiyohiko Nakajima、Yasushi Nishihara

  DOI：10.1021/acs.orglett.6b00503

  日期：2016.4.1

  Palladium-catalyzed carbothiolation of terminal alkynes with azolyl sulfides affords various 2-(azolyl)alkenyl sulfides with perfect regio- and stereoselectivities. The present addition reaction proceeded through a direct cleavage of carbon–sulfur bonds in azolyl sulfides. The resulting adducts that are useful intermediates in organic synthesis are further transformed to multisubstituted olefins containing

  末端炔烃与偶氮基硫醚的钯催化碳硫键合反应可提供具有完美的区域选择性和立体选择性的各种2-（偶氮基）烯基硫醚。目前的加成反应是通过直接裂解偶氮基硫醚中的碳硫键进行的。将所得的在有机合成中有用的中间体的加合物进一步转化为含有偶氮基部分的多取代烯烃。
• Substituted oxazoles and thiazoles as herbicides
  申请人：Sandoz, Inc.

  公开号：US04022607A1

  公开（公告）日：1977-05-10

  Substituted oxazoles and thiazoles are useful as herbicides.

  替代氧唑并噻唑可作为除草剂。