6-溴苯并[d]噻唑-2-甲腈 | 741253-03-2

• 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: 6-溴苯并[d]噻唑-2-甲腈
• 中文别名: 6-溴苯并[D]噻唑-2-甲腈；6-溴-2-苯并噻唑
• 英文名称: 6-bromobenzo[d]thiazole-2-carbonitrile
• 英文别名: 6-bromo-1,3-benzothiazole-2-carbonitrile
• CAS: 741253-03-2
• 化学式: C₈H₃BrN₂S
• 分子量: 239.095
• InChiKey: LITDULGWAMMAPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  6-溴苯并[d]噻唑-2-甲腈 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 1,4-二氧六环 、 aq. phosphate buffer 、 乙腈 为溶剂， 反应 7.5h， 生成 (S)-2-(6-(cyclopropanesulfonamido)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
  参考文献：
  名称：

  Sulfonamides Are an Overlooked Class of Electron Donors in Luminogenic Luciferins and Fluorescent Dyes

  摘要：

  Many fluorophores, and all bright light-emitting substrates for firefly luciferase, contain hydroxyl or amine electron donors. Sulfonamides were found to be capable of serving as replacements for these canonical groups. Unlike "caged" carboxamides, sulfonamide donors enable bioluminescence, and sulfonamidyl luciferins, coumarins, rhodols, and rhodamines are fluorescent in water.

  DOI：

  10.1021/acs.orglett.9b00173
• 作为产物：
  描述：

  2,4-二溴苯胺 在 吡啶 、 copper(l) iodide 作用下， 以 二氯甲烷 为溶剂， 20.0~115.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 生成 6-溴苯并[d]噻唑-2-甲腈
  参考文献：
  名称：

  新型N-（4-苯基噻唑-2-基）-苯并[ d ]噻唑-，噻唑并[4,5- b ]吡啶-，噻唑并[5,4- b ]吡啶-和苯并[ d ]的微波辅助合成] oxazole-2-carboximidamides受海洋托泊汀和正托泊汀的启发

  摘要：

  我们报告了新型N-（4-苯基噻唑-2-基）取代的苯并[ d ]噻唑-，噻唑并[4,5- b ]吡啶-，噻唑并[5,4- b ]吡啶-和苯并[ d ] oxazole-2-carboximidamides，其灵感来自海洋托泊汀和正托泊汀。4，5-二氯-1，2，3-二噻唑鎓氯化物（阿佩尔盐）与各种邻卤代苯胺，氨基吡啶和氨基酚的缩合反应可制得相应的芳基二噻唑，收率良好或优异。铜（I）介导或亲核辅助的芳基二噻唑提供氰基官能化的苯并[ d ]噻唑，噻唑[4,5- b ]-和噻唑[5,4- b]]-吡啶和苯并[ d ]恶唑。将后者与取代的4-苯基噻唑-2-胺缩合，以中等至良好的产率提供二十七种新的多芳族羧酰亚胺。

  DOI：

  10.1016/j.tet.2014.06.102

文献信息

• Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors
  作者：Deepak K. Sharma、Spencer T. Adams、Kate L. Liebmann、Stephen C. Miller

  DOI：10.1021/acs.orglett.7b02806

  日期：2017.11.3

  Light-emitting firefly luciferin analogues contain electron-donating groups in the 6′-position, but the scope of known 6′-substitution remains narrow. A two-step route to a broad range of 6′-substituted luciferin analogues was developed to fill this void and enable more extensive study of the 6′-functionality. This chemistry allowed direct access to “caged” amide and bright azetidine analogues, but also

  发光萤火虫萤光素类似物在 6'-位含有供电子基团，但已知 6'-取代的范围仍然很窄。开发了一种获得广泛 6'-取代的荧光素类似物的两步路线，以填补这一空白，并能够对 6'-功能进行更广泛的研究。这种化学反应可以直接获得“笼状”酰胺和明亮的氮杂环丁烷类似物，但也揭示了硫醚抑制剂和出人意料的发光芳胺衍生物。
• Signalling compounds for use in methods of detecting hydrogen peroxide
  申请人：——

  公开号：US20040171098A1

  公开（公告）日：2004-09-02

  Compounds useful for detecting a source of hydrogen peroxide are disclosed wherein a signalling compound of the formula: 1 is reacted with peroxide. Sig is an aromatic or heteroaromatic ring group, B is a boron atom, and R 5 and R 6 are independently selected from hydrogen and lower alkyl groups and can be joined together as a straight or branched alkylene chain forming a five or six-membered ring. A detectable product compound of the formula Sig-OH Is produced and detected by measuring color, fluorescence, chemiluminescence, or bioluminescence. The signalling compound itself does not possess the detectable property or does so only to a very weak degree. The compounds can be used for detection in assays for peroxide or peroxide-producing enzymes and in assays employing enzyme-labeled specific binding pairs.

  本发明揭示了一种用于检测过氧化氢来源的化合物，其中公式1的信号化合物与过氧化物反应。Sig是芳香或杂芳基环团，B是硼原子，R5和R6分别选自氢和低碳基团，并可以连接成直链或支链烷基链形成五元或六元环。产生公式Sig-OH的可检测产物化合物，并通过测量颜色，荧光，化学发光或生物发光来检测。信号化合物本身不具有可检测性或只具有非常弱的可检测性。这些化合物可用于检测过氧化物或产生过氧化物的酶的测定以及使用酶标记的特异性结合对的测定。
• Direct Transformation of Nitrogen-Containing Methylheteroarenes to Heteroaryl Nitrile by Sodium Nitrite
  作者：Chenhui Jiang、Yuqin Chen、Pan Gao、Shuwei Zhang、Xiaodong Jia、Yu Yuan

  DOI：10.1021/acs.orglett.2c02596

  日期：2022.9.2

  The cyanation reaction of methylheteroarenes with acetyl chloride and sodium nitrite via the radical process in high yields is reported. According to the control experiments, the reaction mechanism underwent radical progress. It is very useful in the pharmacy industry due to its metal-free and easy treatment conditions.

  报道了甲基杂芳烃与乙酰氯和亚硝酸钠通过自由基过程以高收率进行的氰化反应。根据对照实验，反应机理发生了根本性的进展。由于其不含金属且易于处理的条件，它在制药行业非常有用。
• Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides
  作者：Nathan Broudic、Alexandra Pacheco-Benichou、Corinne Fruit、Thierry Besson

  DOI：10.3390/molecules27238426

  日期：——

  We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air, using 2.0 equiv of an inorganic additive (KI). In many cases, the reaction led to a sole product regioselectively obtained in

  我们在此报告了一种涉及钯和铜的催化系统，以实现 N-芳基氰基硫代甲酰胺的环化和 2-氰基苯并噻唑的合成。CH 功能化/分子内 CS 键形成反应是在空气存在下使用 2.0 当量的无机添加剂 (KI) 实现的。在许多情况下，该反应导致以高收率区域选择性获得的唯一产物，允许合成范围广泛的取代 2-氰基苯并噻唑衍生物，为设计更复杂的杂环或分子标记系统提供有价值的构建模块。
• Signalling compounds and methods for detecting hydrogen peroxide
  申请人：——

  公开号：US20040166539A1

  公开（公告）日：2004-08-26

  Methods and compound useful for detecting a source of hydrogen peroxide are disclosed wherein a signalling compound of the formula: 1 is reacted with peroxide. Sig is a non-polymeric organic group, B is a boron atom, and each R is independently selected from hydrogen, alkyl and aryl groups and can be joined together as a straight or branched alkylene chain forming a ring or as an aromatic ring. A detectable product compound of the formula Sig-OH or Sig-O − is produced and detected by measuring color, absorbance, fluorescence, chemiluminescence, or bioluminescence. The signalling compound itself does not possess the detectable property or does so only to a very weak degree. The methods can be used as a detectable signal in assays for peroxide or peroxide-producing enzymes and in assays employing enzyme-labeled specific binding pairs.

  本发明公开了用于检测过氧化氢来源的方法和化合物，其中含有一种式如下的信号化合物： 1 与过氧化氢反应。Sig 是非聚合有机基团，B 是硼原子，每个 R 独立地选自氢、烷基和芳基，可作为形成环的直链或支链亚烷基链或作为芳香环连接在一起。式 Sig-OH 或 Sig-O - 产生，并通过测量颜色、吸光度、荧光、化学发光或生物发光进行检测。信号化合物本身不具有可检测特性，或仅具有非常微弱的可检测特性。这些方法可在过氧化物或产生过氧化物的酶的检测中以及在采用酶标记的特异性结合对的检测中用作可检测信号。