2-bromo-5-chloro-3-methylthiophene | 53374-61-1

• 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-bromo-5-chloro-3-methylthiophene
• CAS: 53374-61-1
• 化学式: C₅H₄BrClS
• 分子量: 211.51
• InChiKey: RPIZMUZGZZSEJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  208.9±35.0 °C(Predicted)
• 密度：
  1.715±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-5-chloro-3-methylthiophene 在 aluminum oxide 、 sodium methylate 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 5-methoxy-3-methylthien-2-yl (3-methylthien-2-yl)methanone
  参考文献：
  名称：

  The synthesis of novel GABA uptake inhibitors. Part 2. Synthesis of 5-hydroxytiagabine, a human metabolite of the GABA reuptake inhibitor tiagabine

  摘要：

  (R)-1-(4-(2,5-Dihydro-3-methyl-5-oxothien-2-ylidene)-4-(3-methyl-2-thienyl)butyl)-3- piperidinecarboxylic acid (5-hydroxytiagabine) 13, has been prepared in 8 steps from 2-bromo-3-methylthiophene 3. Key steps are Grignard reactions, displacement of heteroaromatic chlorine with methoxy, and simultaneously demethylation and opening of a hydroxymethylcyclopropane with bromotrimethylsilane. An alternative approach involving acylation of 2-lithio-3-methylthiophene 17a was found less satisfying. A metalloporphyrin assisted hydroxylation of tiagabine 1 also yielded the target metabolite. The structure of 5-hydroxytiagabine was confirmed by NMR-data including COSY, ROESY, HMQC and HMBC experiments.

  DOI：

  10.1016/s0040-4020(01)85345-x
• 作为产物：
  描述：

  2-溴-3-甲基噻吩 以20%的产率得到2-bromo-5-chloro-3-methylthiophene
  参考文献：
  名称：

  The synthesis of novel GABA uptake inhibitors. Part 2. Synthesis of 5-hydroxytiagabine, a human metabolite of the GABA reuptake inhibitor tiagabine

  摘要：

  (R)-1-(4-(2,5-Dihydro-3-methyl-5-oxothien-2-ylidene)-4-(3-methyl-2-thienyl)butyl)-3- piperidinecarboxylic acid (5-hydroxytiagabine) 13, has been prepared in 8 steps from 2-bromo-3-methylthiophene 3. Key steps are Grignard reactions, displacement of heteroaromatic chlorine with methoxy, and simultaneously demethylation and opening of a hydroxymethylcyclopropane with bromotrimethylsilane. An alternative approach involving acylation of 2-lithio-3-methylthiophene 17a was found less satisfying. A metalloporphyrin assisted hydroxylation of tiagabine 1 also yielded the target metabolite. The structure of 5-hydroxytiagabine was confirmed by NMR-data including COSY, ROESY, HMQC and HMBC experiments.

  DOI：

  10.1016/s0040-4020(01)85345-x

文献信息

• Derivatives of thiophene-2-carboxylic acid and their pharmaceutically
  申请人：Laevosan-Gesellschaft m.b.H. & Co. KG

  公开号：US04590203A1

  公开（公告）日：1986-05-20

  The disclosure is directed to new derivatives of thiophene-2-carboxylic acid and the pharmaceutically acceptable acid or base addition salts thereof as well as to the process for the preparation thereof. The compounds of the invention have the structural formula ##STR1## in which R in position 3 or 4 of the thiophene nucleus is hydrogen, methyl, chlorine or bromine and R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl. The compounds have a remarkably strong inhibitory effect on the thromboxane synthetase and are useful for the treatment of conditions such as inflammation, hypertension, thrombus, apoplexy, asthma, angina pectoris, ischemic heart diseases, ischemic conditions, migraine and vascular complications in connection with diabetes.

  该披露涉及噻吩-2-羧酸的新衍生物及其药用可接受的酸或碱盐，以及其制备方法。该发明的化合物具有下列结构式：##STR1##其中噻吩核的第3或第4位的R为氢、甲基、氯或溴，R.sub.1为氢或C.sub.1-C.sub.4-烷基。这些化合物对血栓素合酶有明显的强抑制作用，可用于治疗炎症、高血压、血栓、中风、哮喘、心绞痛、缺血性心脏病、缺血性疾病、偏头痛以及与糖尿病相关的血管并发症。
• [EN] HETEROARYL-SUBSTITUTED MACROCYCLIC FLU ENDONUCLEASE INHIBITORS<br/>[FR] INHIBITEURS MACROCYCLIQUES D'ENDONUCLÉASE DE LA GRIPPE SUBSTITUÉS PAR HÉTÉROARYLE
  申请人：JANSSEN BIOPHARMA INC

  公开号：WO2021191872A1

  公开（公告）日：2021-09-30

  The present invention relates to heteroaryl-substituted macrocyclic compounds and prodrugs thereof, and pharmaceutically acceptable salts, solvates, and polymorphs thereof, and the use of such compounds as a medicament, in particular in the prevention and/or treatment of viral infections caused by viruses belonging to the Orthomyxoviridae family. The present invention furthermore relates to pharmaceutical compositions or combination preparations of the compounds, and to the compositions or preparations for use as a medicament, more preferably for the prevention or treatment of viral infections caused by viruses belonging to the Orthomyxoviridae family.

  本发明涉及杂环取代的大环化合物及其前药，以及其药学上可接受的盐、溶剂化合物和多型体，以及将这些化合物作为药物的用途，特别是用于预防和/或治疗由属于Orthomyxoviridae家族的病毒引起的病毒感染。本发明还涉及该化合物的药物组合物或混合制剂，以及用作药物的组合物或制剂，更好地用于预防或治疗由属于Orthomyxoviridae家族的病毒引起的病毒感染。
• Ethynylene acene polymers
  申请人：Li Yuning

  公开号：US20070238855A1

  公开（公告）日：2007-10-11

  A polymer of Formula or structure (I) wherein at least one of R 1 and R 2 is a suitable hydrocarbon, hydrogen, a heteratom containing group, or a halogen; Ar and Ar′ represent an aromatic moiety; x, y, a, b, c, d, e, f, and g represent the number of groups or rings, respectively; and n represents the number of repeating units.

  一种公式或结构（I）的聚合物，其中R1和R2中至少有一个是适当的碳氢化合物，氢，含杂原子的基团或卤素; Ar和Ar'代表芳香基团; x，y，a，b，c，d，e，f和g分别表示组或环的数量; n代表重复单元的数量。
• Process for the preparation of a borylated thiophene
  申请人：Smith R. Milton

  公开号：US20080091035A1

  公开（公告）日：2008-04-17

  Borylated thiophenes are prepared by the process. The borylated thiophenes are intermediates to thiophene polymers for electronic applications.

  Borylated thiophenes通过该过程制备。Borylated thiophenes是用于电子应用的噻吩聚合物的中间体。
• Thiophen-2-carbonsäurederivate und Verfahren zu deren Herstellung
  申请人：Laevosan-Gesellschaft m.b.H.

  公开号：EP0109381A1

  公开（公告）日：1984-05-23

  Neue Thiophen-2-carbonsäurederivate der allgemeinen Formel worin R in Stellung 3 oder 4 des Thiophenkerns Wasserstoff, Methyl, Chtor oder Brom und R1 Wasserstoff oder C1-C4-Alkyl bedeuten, und ihre pharmazeutisch verträglichen Säure- oder Basenadditionssalze besitzen eine starke Hemmungswirkung auf die Thromboxansynthetase und sind somit zur Behandlung von Krankheiten geeignet, die durch Thromboxan A2 verursacht werden. z.B. Entzündungen, hoher Blutdruck, Thrombus, Gehirnscniag. Asthma, Angina pectoris, ischämische Herzleiden, schamische Anfälle, Migräne und vaskuläre Komplikationen von Diabetes.

  通式如下的新型噻吩-2-羧酸衍生物 其中噻吩核的第 3 位或第 4 位上的 R 是氢、甲基、氯或溴，R1 是氢或 C1-C4- 烷基，及其药学上可接受的酸或碱加成盐对血栓素合成酶有很强的抑制作用，因此适用于治疗由血栓素 A2 引起的疾病，如炎症、高血压、血栓、脑痉挛、哮喘、心绞痛、缺血性心脏病、缺血性发作、偏头痛和糖尿病的血管并发症。哮喘、心绞痛、缺血性心脏病、缺血性发作、偏头痛和糖尿病血管并发症。