3-chloro-4-(thiophen-2-yl)-1,2,5-thiadiazole | 157928-66-0

• 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: 3-chloro-4-(thiophen-2-yl)-1,2,5-thiadiazole
• 英文别名: 1,2,5-Thiadiazole, 3-chloro-4-(2-thienyl)-；3-chloro-4-thiophen-2-yl-1,2,5-thiadiazole
• CAS: 157928-66-0
• 化学式: C₆H₃ClN₂S₂
• 分子量: 202.688
• InChiKey: KXHLMUHWKXREKK-UHFFFAOYSA-N

物化性质

• 沸点：
  269.9±25.0 °C(Predicted)
• 密度：
  1.534±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-三丁基甲锡烷基噻吩 、 3,4-二氯-1,2,5-噻二唑 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以47%的产率得到3-chloro-4-(thiophen-2-yl)-1,2,5-thiadiazole
  参考文献：
  名称：

  The Palladium-catalyzed Cross-Coupling Reactions of 3-Chloro-4-halogeno-1,2,5-thiadiazoles

  摘要：

  3,4-Dichloro- and 3-chloro-4-halogeno-1,2,5-thiadiazoles (halogeno-: bromo- and iodo-) are involved in Pd-catalyzed cross-coupling reactions under Stille and Suzuki conditions. As a result, by using the commercially available 3,4-dichloro-1,2,5-thiadiazole as substrate, several 3-alkyl-, 3-alkenyl-, 3-alkynyl-and 3-aryl-4-chloro-1,2,5-thiadiazoles can easily be prepared. However, these reactions through direct desymmetrization of the 3,4-dichloro-1,2,5-thiadiazole always occur with side-reactions resulting from the concurrent decomposition of the heterocyclic ring of the starting material. These problems are resolved by involving, in these Pd-catalyzed cross-coupling reactions, the more reactive and selective 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole. These new dihalogeno-1,2,5-thiadiazoles can easily be prepared, via diazotization reaction followed by halogen substitution, from the 3-amino-4-chloro-1,2,5-thiadiazole.

  DOI：

  10.3987/com-02-9550

文献信息

• Palladium-catalyzed cross-coupling chemistry on 3-chloro-4-halo-1,2,5-thiadiazole
  申请人：Eli Lilly and Company

  公开号：US06620940B1

  公开（公告）日：2003-09-16

  The present invention relates to 3-chloro-4-halo-1,2,5-thiadiazole compounds, a method of producing novel mono- and di-substituted-1,2,5-thiadiazoles therefrom, as well as mono- and di-substituted -1,2,5-thiadiazoles.

  本发明涉及3-氯-4-卤代-1,2,5-噻二唑化合物，一种从中制备新型单取代和双取代-1,2,5-噻二唑的方法，以及单取代和双取代-1,2,5-噻二唑。
• [EN] 1,2,5-THIADIAZOLE DERIVATIVES, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE 1,2,5-THIADIAZOLE, LEUR PREPARATION ET LEUR UTILISATION
  申请人：NOVO NORDISK A/S

  公开号：WO1994027996A1

  公开（公告）日：1994-12-08

  (EN) 1,2,5-thiadiazole derivatives of formula (I) wherein A is a straight or branched, saturated acyclic hydrocarbon of 2-6 carbon atoms; Y is CH or N; X is O, S, NH, NCH3, or CH2; R1 is 1,2-benzisothiazol-3-yl, 1,2-benzisoxazol-3-yl, 1H-indazol-3-yl, or 1-methyl-1H-indazol-3-yl, all of which may be substituted; or R1 is 4-fluorobenzoyl or phenyl optionally substituted; R2 is optionally substituted aryl or heteroaryl; and pharmaceutically acceptable salts thereof are useful in the treatment of indications related to the CNS-system, cardiovascular system or to gastrointestinal disorders.(FR) L'invention concerne des dérivés de 1,2,5-thiadiazole selon la formule (I) dans laquelle A représente un hydrocarbure acyclique saturé de 2 à 6 atomes de carbone, droit ou ramifié; Y représente CH ou N; X représente O, S, NH, NCH3 ou CH2; R1 représente 1,2-benzisothiazol-3-yle, 1,2-benzisoxazol-3-yle, 1H-indazol-3-yle ou 1-méthyle-1H-indazol-3-yle, pouvant tous être substitués; ou R1 représente 4-fluorobenzoyle ou phényle optionnellement substitué; R2 représente aryle ou hétéroaryle optionnellement substitué. L'invention décrit également les sels pharmaceutiquement acceptables de ces dérivés. Ces dérivés et leurs sels sont utiles dans le traitement des indications concernant le système nerveux central, le système cardio-vasculaire ou les maladies gastro-intestinales.

  1,2,5-噻ioxazole衍生物，其化学式为(I)，其中，A为直链或分枝的不超过6碳原子的饱和非环状烷烃，Y为CH或N，X为O、S、NH、NCH3或CH2，R1为1,2-苯并噻ioxazole-3-yl，1,2-苯并单环氧化物-3-yl、1H-并配备了的咪唑-3-yl或1-甲基的1H-并的咪唑-3-yl（均可被取代），或R1为4-氟-苯甲酸或苯甲基可能被取代，R2为可能被取代的苯环或杂环，并且这些化合物的 pharmaceutically 可接受的 盐类 在中枢神经、心血管或消化系统相关病症的治疗中是十分有用的。
• US6620940B1
  申请人：——

  公开号：US6620940B1

  公开（公告）日：2003-09-16
• The Palladium-catalyzed Cross-Coupling Reactions of 3-Chloro-4-halogeno-1,2,5-thiadiazoles
  作者：Alain Merschaert、Hugo J. Gorissen

  DOI：10.3987/com-02-9550

  日期：——

  3,4-Dichloro- and 3-chloro-4-halogeno-1,2,5-thiadiazoles (halogeno-: bromo- and iodo-) are involved in Pd-catalyzed cross-coupling reactions under Stille and Suzuki conditions. As a result, by using the commercially available 3,4-dichloro-1,2,5-thiadiazole as substrate, several 3-alkyl-, 3-alkenyl-, 3-alkynyl-and 3-aryl-4-chloro-1,2,5-thiadiazoles can easily be prepared. However, these reactions through direct desymmetrization of the 3,4-dichloro-1,2,5-thiadiazole always occur with side-reactions resulting from the concurrent decomposition of the heterocyclic ring of the starting material. These problems are resolved by involving, in these Pd-catalyzed cross-coupling reactions, the more reactive and selective 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole. These new dihalogeno-1,2,5-thiadiazoles can easily be prepared, via diazotization reaction followed by halogen substitution, from the 3-amino-4-chloro-1,2,5-thiadiazole.