2-甲基-6-氰基苯并噻唑 | 42474-60-2

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-甲基-6-氰基苯并噻唑
• 中文别名: 2-甲基苯并[D]噻唑-6-甲腈
• 英文名称: 2-methylbenzo[d]thiazole-6-carbonitrile
• 英文别名: 2-methylbenzothiazole-6-carbonitrile；2-methylbenzothiazol-6-carbonitrile；2-methyl-benzothiazole-6-carbonitrile；2-Methyl-benzothiazol-6-carbonitril；2-methyl-6-cyanobenzothiazole；Cyano-6-methyl-2-Benzothiazol；2-methyl-1,3-benzothiazole-6-carbonitrile
• CAS: 42474-60-2
• 化学式: C₉H₆N₂S
• mdl: MFCD16619173
• 分子量: 174.226
• InChiKey: BSQUFWQEXRABMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144℃
• 沸点：
  325.1±15.0 °C(Predicted)
• 密度：
  1.30

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934200090

反应信息

• 作为反应物：
  描述：

  2-甲基-6-氰基苯并噻唑 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 72.0h， 生成 2-[4-((S)-1-tert-Butoxycarbonyl-pyrrolidin-3-yloxy)-phenyl]-2-(6-cyano-benzothiazol-2-ylmethyl)-malonic acid diethyl ester
  参考文献：
  名称：

  Design, synthesis and biological activity of amidinobicyclic compounds (derivatives of DX-9065a) as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Since factor Xa (fXa) plays a pivotal role in the blood coagulation cascade, inhibition of fXa is thought to be an effective treatment for a variety of thrombotic events. (2,)-2-[4-[[(3S)-l-Acetimidoyl-3-pyrrolidinyl]oxy]phenyl]-3-(7-amidino-2-naphthyl)propanoic acid hydrochloride pentahydrate (DX-9065a) was previously found in our laboratory as a novel orally active factor Xa inhibitor. DX-9065a exhibits a strong inhibitory activity toward fXa by occupying the substrate recognition (called SI) sites and aryl binding sites of fXa. Herein we describe conversions of the amidinonaphthalene and the acetimidoylpyrrolidine moieties of DX-9065a. Some compounds showed remarkably increased in vitro anti-factor Xa and PRCT activities compared with those of DX9065a. The most promising compound 38 showed four times the prolongation of APTT against DX-9065a after oral administration to rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.032
• 作为产物：
  描述：

  N-(4-cyano-2-iodophenyl)acetamide 在 sodiumsulfide nonahydrate 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以72%的产率得到2-甲基-6-氰基苯并噻唑
  参考文献：
  名称：

  可回收的铜催化邻卤代苯胺和金属硫化物的环化：一种高效实用的取代苯并噻唑

  摘要：

  在 MCM-41 结合的 NHC-Cu(I) 催化剂存在下，通过 DMF 中的 C-S 偶联，在 80 或 140 °C 下实现了有效的多相铜催化的邻卤代苯胺和金属硫化物环化，然后分子内缩合，以良好至高产率提供范围广泛的取代苯并噻唑。这种新的 MCM-41-NHC-CuI 复合物可以通过两步程序轻松获得，从易于获得且价格低廉的试剂开始，并重复使用七次以上，而不会显着降低其催化效率。本协议已成功应用于两种抗肿瘤剂 5F203 和 PMX 610 的克级合成。

  DOI：

  10.1016/j.mcat.2022.112115

文献信息

• Azole antifungal agents, processes for the preparation thereof, and intermediates
  申请人：Eisai Co., Ltd.

  公开号：EP1231210A2

  公开（公告）日：2002-08-14

  A compound represented by the general formula: wherein R1 and R2 denote a halogen atom or hydrogen atoms; R3 means a hydrogen atoms or lower alkyl group; r and m stand for 0 or 1; A is N or CH; W denotes an aromatic ring or a condensed ring thereof; X means another aromatic rings, an alkanediyl group, an alkenediyl group, or an alkynediyl group; Y stand for -S-, etc.; Z denotes a hydrogen atom, etc., or a salt thereof, and intermediates thereof or a salt thereof as well as processes for the preparation thereof, and pharmacetical composition suitable for use as an antifungal agent.

  通用公式表示的化合物为： 其中R1和R2表示卤素原子或氢原子；R3表示氢原子或较低的烷基基团；r和m代表0或1；A为N或CH；W表示芳香环或其缩合环；X表示另一个芳香环、烷二基基团、烯二基基团或炔二基基团；Y代表-S-等；Z表示氢原子等，或其盐，以及其中间体或其盐，以及用作抗真菌剂的制备方法和适用的药物组合物。
• A room temperature cyanation of (hetero)aromatic chlorides by an air stable nickel(<scp>ii</scp>) XantPhos precatalyst and Zn(CN)₂
  作者：D. Dawson Beattie、Thomas Schareina、Matthias Beller

  DOI：10.1039/c7ob00892a

  日期：——

  A methodology for the synthesis of (hetero)aromatic nitriles from aryl chlorides at room temperature has been developed. This methodology uses an air and moisture stable nickel(II) XantPhos precatalyst and Zn(CN)2 as the cyanide (CN-) source.

  已经开发了在室温下由芳基氯合成（杂）芳族腈的方法。该方法使用了对空气和湿气稳定的镍（II）XantPhos预催化剂和Zn（CN）2作为氰化物（CN-）源。
• Preparation of Novel Push-Pull Benzothiazole Derivatives with Reverse Polarity: Compounds with Potential Non-Linear Optic Application
  作者：Peter Hrobárik、Pavol Zahradník、Ivica Sigmundová

  DOI：10.1055/s-2004-837309

  日期：——

  The hitherto unknown 6-dimethylaminobenzothiazole-2-carbaldehyde was prepared as a starting compound for the synthesis of novel push-pull benzothiazole derivatives with reverse polarity. These compounds are substituted at the 2-position by strong electron-acceptor groups and at the 6-position by NMe2 as strong electron-donor. The new method for synthesis of 6-dimethylaminobenzothiazole involved the successful use of sonochemical reductive methylation. Expected non-linear optical properties of target molecules were studied by EFISH method.

  此前未知的6-二甲氨基苯噻唑-2-甲醛被制备为合成具有反向极性的创新性推拉苯噻唑衍生物的起始化合物。这些化合物在2位被强电子接受基团取代，在6位被NMe2作为强电子给予基团取代。6-二甲氨基苯噻唑的合成新方法成功地采用了超声化学还原甲基化。目标分子的预期非线性光学性质通过EFISH方法进行了研究。
• Synthesis and Study of Novel Benzothiazole Derivatives with Potential Nonlinear Optical Properties
  作者：Ivica Sigmundová、Pavol Zahradník、Dušan Loos

  DOI：10.1135/cccc20071069

  日期：——

  The synthesis of new benzothiazole push-pull systems as candidates for NLO-phores is described. Spectral (UV/VIS and solvatochromic) and theoretical studies (electronic properties based on semiempirical AM1 and PM3 methods) of the prepared compounds were carried out. The structure and physico-chemical parameters affecting the push-pull character and intramolecular charge transfer (ICT) of the studied compounds have been investigated and compounds with enhanced hyperpolarizability β have been predicted. The benzothiazolium salts were found to be much more effective NLO-phores in comparison with the corresponding neutral benzothiazoles. The 4-NPh₂ group is the most effective donor. The extension of conjugated bridge improves the studied NLO characteristics. An additional acceptor group bonded to the heterocycle causes a red shift of λ_max but does not increase hyperpolarizability.

  描述了合成新的苯并噻唑推-拉系统作为NLO荧光团的候选物。对所制备化合物进行了光谱（UV/VIS和溶剂致色性）和理论研究（基于半经验AM1和PM3方法的电子性质）。研究了影响推-拉性质和分子内电荷转移（ICT）的结构和物理化学参数，并预测了具有增强高极化率β的化合物。与相应的中性苯并噻唑相比，苯并噻唑盐在NLO荧光团中表现出更高的效果。4-NPh2基团是最有效的给体。共轭桥的延伸改善了研究的NLO特性。附加的受体基团与杂环相结合导致了λmax的红移，但并不增加高极化率。
• OXAZINE DERIVATIVES AND A PHARMACEUTICAL COMPOSITION FOR INHIBITING BACE1 CONTAINING THEM
  申请人：Masui Moriyasu

  公开号：US20140051691A1

  公开（公告）日：2014-02-20

  The present invention provides a compound of formula (I): wherein —X═ is —CR 7 ═ or —N═, ring B is a substituted or unsubstituted carbocycle or a substituted or unsubstituted heterocycle, R 1 is substituted or unsubstituted alkyl or the like, R 2 a and R 2 b are each independently hydrogen, substituted or unsubstituted alkyl or the like, R 3 and R 4 are each independently hydrogen, halogen, substituted or unsubstituted alkyl or the like, R 5 is hydrogen, substituted or unsubstituted alkyl or the like, each R 6 is independently halogen, hydroxy, substituted or unsubstituted alkyl or the like, R 7 is hydrogen, halogen, hydroxy, substituted or unsubstituted alkyl or the like, p is an integer of 0 to 3, or a pharmaceutically acceptable salt thereof which has an effect of inhibiting amyloid β production, especially an effect of inhibiting BACE1, and which is useful as a therapeutic or prophylactic agent for diseases induced by production, secretion and/or deposition of amyloid β proteins.

  本发明提供了一种化合物的公式(I)：其中—X═是—CR7═或—N═，环B是取代或未取代的碳环或取代或未取代的杂环，R1是取代或未取代的烷基或类似物，R2和R2'分别独立地是氢、取代或未取代的烷基或类似物，R3和R4分别独立地是氢、卤素、取代或未取代的烷基或类似物，R5是氢、取代或未取代的烷基或类似物，每个R6独立地是卤素、羟基、取代或未取代的烷基或类似物，R7是氢、卤素、羟基、取代或未取代的烷基或类似物，p是0到3的整数，或其在药学上可接受的盐，具有抑制淀粉样蛋白β产生的作用，特别是抑制BACE1的作用，并且可用作由淀粉样蛋白β蛋白的产生、分泌和/或沉积引起的疾病的治疗或预防剂。