6-methoxy-2-(trifluoromethyl)benzo[d]thiazole | 1188087-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-methoxy-2-(trifluoromethyl)benzo[d]thiazole
• 英文别名: 6-methoxy-2-(trifluoromethyl)-1,3-benzothiazole
• CAS: 1188087-91-3
• 化学式: C₉H₆F₃NOS
• 分子量: 233.214
• InChiKey: RNLOCLFMUTWONY-UHFFFAOYSA-N

物化性质

• 熔点：
  34 °C
• 沸点：
  233.8±40.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-辛炔 、 6-methoxy-2-(trifluoromethyl)benzo[d]thiazole 在 bis(1,5-cyclooctadiene)nickel (0) 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 正己烷 为溶剂， 反应 15.0h， 以96%的产率得到3,4-dipropyl-6-methoxy-2-trifluoromethylquinoline
  参考文献：
  名称：

  （三氟甲基）喹啉的新合成路线：镍催化通过形成硫镍环和热脱硫将炔烃插入芳族 C-S 键

  摘要：

  我们开发了一种炔烃在镍催化下插入 2-（三氟甲基）-1,3-苯并噻唑的反应，得到七元苯并噻氮杂，通过热脱硫作用转化为 2-（三氟甲基）喹啉。这个过程可以被认为是硫原子用炔烃的形式取代。通过 X 射线单晶结构分析和原位 X 射线吸收精细结构光谱证实了通过将苯并噻唑中的 C-S 键氧化加成到镍 (0) 上而形成的硫镍环中间体的结构。

  DOI：

  10.1055/s-0037-1610785
• 作为产物：
  描述：

  2,2,2-trifluoro-N-(4-methoxyphenyl)thioacetamide 在 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以83%的产率得到6-methoxy-2-(trifluoromethyl)benzo[d]thiazole
  参考文献：
  名称：

  A General and Straightforward Method for the Synthesis of 2-Trifluoromethylbenzothiazoles

  摘要：

  An efficient one-pot method for the synthesis of 2-trifluoromethylbenzothiazoles by the treatment of trifluoromethylimidoyl chlorides with sodium hydrosulfide hydrate using PdCl(2) as the sole catalyst in DMSO is described. The reaction proceeds via thiolation/C H bond functionalization/C S bond formation in moderate to high yields with good functional group tolerance.

  DOI：

  10.1021/ol1006899

文献信息

• URAT1 INHIBITOR
  申请人：Nippon Chemiphar Co., Ltd.

  公开号：US20170290795A1

  公开（公告）日：2017-10-12

  Provided are a compound represented by the following Formula (III), a tautomer or stereoisomer of the compound, or a pharmaceutically acceptable salt or solvate thereof used as a therapeutic agent for gout or hyperuricemia. (In the Formula (III), R 1a , R 2a , R 6a , and R 7a represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a cyano group, R 3a and R 8a form a benzene ring or a 5-membered heteroaryl ring containing 1 to 3 heteroatoms, as a ring constituent element, selected from nitrogen atoms, oxygen atoms, and sulfur atoms together with two carbon atoms to which R 3a and R 8a are bonded, R 4a and R 5a form a benzene ring together with two carbon atoms to which R 4a and R 5a are bonded or represent any of the groups represented by R 1a described above, W a represents CR 10a or N, and where, R 10a represents any of the groups represented by R 1a , X a represents an oxygen atom or a sulfur atom, Y a represents an alkylene chain having 1 to 8 carbon atoms, and where, the alkylene chain may be substituted with an alkyl group having 1 to 8 carbon atoms and the alkylene chain may be a linear or branched alkylene chain, the branched alkylene chain may have a 3- to 7-membered ring formed by side chains bonded to carbon atoms which are the same as or different from each other, together with the carbon atoms to which the side chains are bonded and may have a double bond in the middle thereof, and Z a represents CO 2 H.)

  提供的是以下公式（III）所代表的化合物，该化合物的互变异构体或立体异构体，或者是作为痛风或高尿酸血症治疗剂的药用可接受盐或溶剂。（在公式（III）中，R1a、R2a、R6a和R7a代表氢原子、具有1至8个碳原子的烷基、具有1至8个碳原子的烷氧基或氰基，R3a和R8a形成苯环或含有1至3个杂原子（从氮原子、氧原子和硫原子中选择）的5元杂环，作为环构成元素，与R3a和R8a结合的两个碳原子一起，R4a和R5a与R4a和R5a结合的两个碳原子一起形成苯环，或代表上述R1a描述的任何基团，W代表CR10a或N，其中R10a代表上述R1a描述的任何基团，X代表氧原子或硫原子，Y代表具有1至8个碳原子的烷基链，其中烷基链可能被具有1至8个碳原子的烷基取代，且烷基链可能是直链或支链烷基链，支链烷基链可能由连接到相同或不同的碳原子的侧链形成3至7个成员环，与侧链结合的碳原子以及可能在其中间具有双键，并且Z代表CO2H。）
• Sodium Sulfite-Involved Photocatalytic Radical Cascade Cyclization of 2-Isocyanoaryl Thioethers: Access to 2-CF₂/CF₃-Containing Benzothiazoles
  作者：Yao Yuan、Wuheng Dong、Xiaoshuang Gao、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/acs.orglett.8b03710

  日期：2019.1.18

  visible-light-induced radical cascade cyclization of 2-isocyanoaryl thioethers for the synthesis of 2-CF2/CF3-containing benzothiazoles has been developed. Sodium sulfite can participate in the photocatalytic cycle as a reductant that efficiently transforms Ir4+ into Ir3+ to promote the fluoroalkylation under mild reaction conditions.

  已经开发了可见光诱导的2-异氰基芳基硫醚的自由基级联环化反应，用于合成含2-CF 2 / CF 3的苯并噻唑。亚硫酸钠可作为还原剂参与光催化循环，该还原剂可在温和的反应条件下有效地将Ir 4+转化为Ir 3+从而促进氟烷基化。
• URAT1 inhibitor
  申请人：Nippon Chemiphar Co., Ltd.

  公开号：US10173990B2

  公开（公告）日：2019-01-08

  Provided are a compound represented by the following Formula (III), a tautomer or stereoisomer of the compound, or a pharmaceutically acceptable salt or solvate thereof used as a therapeutic agent for gout or hyperuricemia. (In the Formula (III), R1a, R2a, R6a, and R7a represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a cyano group, R3a and R8a form a benzene ring or a 5-membered heteroaryl ring containing 1 to 3 heteroatoms, as a ring constituent element, selected from nitrogen atoms, oxygen atoms, and sulfur atoms together with two carbon atoms to which R3a and R8a are bonded, R4a and R5a form a benzene ring together with two carbon atoms to which R4a and R5a are bonded or represent any of the groups represented by R1a described above, Wa represents CR10a or N, and where, R10a represents any of the groups represented by R1a, Xa represents an oxygen atom or a sulfur atom, Ya represents an alkylene chain having 1 to 8 carbon atoms, and where, the alkylene chain may be substituted with an alkyl group having 1 to 8 carbon atoms and the alkylene chain may be a linear or branched alkylene chain, the branched alkylene chain may have a 3- to 7-membered ring formed by side chains bonded to carbon atoms which are the same as or different from each other, together with the carbon atoms to which the side chains are bonded and may have a double bond in the middle thereof, and Za represents CO2H).

  本发明提供了由下式（III）代表的化合物、该化合物的同分异构体或立体异构体或其药学上可接受的盐或溶液，用作痛风或高尿酸血症的治疗剂。(在式（III）中，R1a、R2a、R6a 和 R7a 代表氢原子、具有 1 至 8 个碳原子的烷基、具有 1 至 8 个碳原子的烷氧基或氰基，R3a 和 R8a 构成苯环或含有 1 至 3 个杂原子的 5 元杂芳基环，作为环组成元素、选自氮原子、氧原子和硫原子，与 R3a 和 R8a 键合的两个碳原子一起，R4a 和 R5a 与 R4a 和 R5a 键合的两个碳原子一起形成苯环，或代表上述 R1a 所代表的任何基团，Wa 代表 CR10a 或 N，其中、R10a 代表 R1a 所代表的任何基团，Xa 代表氧原子或硫原子，Ya 代表具有 1 至 8 个碳原子的亚烷基链，其中，亚烷基链可以被具有 1 至 8 个碳原子的烷基取代，亚烷基链可以是直链或支链亚烷基链、支链亚烷基链可具有一个 3 至 7 元环，该环由与彼此相同或不同的碳原子键合的侧链以及与侧链键合的碳原子形成，并可在其中间具有一个双键，Za 代表 CO2H）。
• N‐Heteroaromatic Fluoroalkylation through Ligand Coupling Reaction of Sulfones
  作者：Huamin Liang、Qian Wang、Xin Zhou、Rongyi Zhang、Min Zhou、Jun Wei、Chuanfa Ni、Jinbo Hu

  DOI：10.1002/anie.202401091

  日期：2024.5.6

  Fluoroalkylated N-heteroarenes are efficiently synthesized from fluoroalkyl 2-azaheteroarylsulfones via Grignard reagent-promoted formal SO2 extrusion reaction. The reaction proceeds through the ligand coupling of a pentacoordinate sulfur(VI) intermediate and exhibits unique fluorine effect.

  通过格氏试剂促进的形式SO 2挤出反应，由氟烷基2-氮杂杂芳基砜有效合成氟烷基化N-杂芳烃。该反应通过五配位硫(VI)中间体的配体偶联进行，并表现出独特的氟效应。
• One–Pot Assembly of 2‐Trifluoromethyl Benzothiazole and Benzoselenazole via Copper–Mediated Three–Component Cascade Reaction
  作者：Yangjie Huang、Chenhui You、Biqiong Hong、Xiaoyan Han、Zhiqiang Weng

  DOI：10.1002/asia.202400331

  日期：2024.7.2

  A domino one–pot synthesis of 2-(trifluoromethyl) benzothiazole via copper–mediated three–component cascade reaction starting from the easily accessible starting materials such as o-iodoanilines, methyl trifluoropyruvate, and elemental sulfur is reported. The present strategy displayed a comprehensive substrate scope and good functional group tolerance and enabled access to a variety of substituted

  据报道，从邻碘苯胺、三氟丙酮酸甲酯和元素硫等容易获得的起始原料开始，通过铜介导的三组分级联反应，多米诺一锅合成2-(三氟甲基)苯并噻唑。本策略显示了全面的底物范围和良好的官能团耐受性，并且能够获得多种取代的2-(三氟甲基)苯并噻唑。还利用该反应方法合成了 2-(三氟甲基)苯并硒唑。