6-氟-1,3-苯并噻唑-2-甲腈 | 169776-04-9

• 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-氟-1,3-苯并噻唑-2-甲腈
• 中文别名: 1H-1,2,4-三唑,5-(1,3-二噁戊环-2-基)-1-甲基-
• 英文名称: 6-fluorobenzo[d]thiazole-2-carbonitrile
• 英文别名: 2-cyano-6-fluorobenzothiazole；6-fluoro-1,3-benzothiazole-2-carbonitrile
• CAS: 169776-04-9
• 化学式: C₈H₃FN₂S
• mdl: MFCD11217287
• 分子量: 178.19
• InChiKey: YMDVORKXEAGKDD-UHFFFAOYSA-N

物化性质

• 沸点：
  297.9±32.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

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：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-氟-1,3-苯并噻唑-2-甲腈 在 硫化氢 作用下， 以 二甲基亚砜 为溶剂， 以80%的产率得到6-fluorobenzo[d]thiazole-2-carbothioamide
  参考文献：
  名称：

  From Liquid to Solid-State Fluorescence: Tricyclic Lactones Based on 4-Hydroxy-1,3-thiazoles

  摘要：

  This work describes the synthesis of a series of tricyclic lactones based on 4-hydroxy-1,3-thiazoles prepared by the classic Hantzsch synthesis. The tricyclic lactones are more rigid than the parent 4-hydroxythiazoles and are featured not only by fluorescence in solution, but also in the solid state. An extension of the chromophoric system was successfully realized by integration of the benzothiazole substructure, thus resulting in bathochromic shifts of absorption and also fluorescence. The new synthesized lactones additionally show interesting properties in solution, whereby the initial blue fluorescence changes dramatically with a variation of the pH value.

  DOI：

  10.1055/s-0033-1340048
• 作为产物：
  描述：

  (2-Bromo-4-fluoro-phenyl)-[4-chloro-[1,2,3]dithiazol-(5Z)-ylidene]-amine 在 copper(l) iodide 作用下， 以 吡啶 为溶剂， 反应 0.17h， 以87%的产率得到6-氟-1,3-苯并噻唑-2-甲腈
  参考文献：
  名称：

  New route to 2-cyanobenzothiazoles via N-arylimino-1,2,3-dithiazoles †

  摘要：

  N-芳基亚氨基-1,2,3-亚硫噻唑衍生物2通过加热或更快速的在常压下用聚焦微波辐射，使用含有碘化亚铜的吡啶，能够高产率转化为2-氰基苯并噻唑3。

  DOI：

  10.1039/a807899h

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。
• [EN] DERIVATIVES OF LUCIFERIN AND METHODS FOR THEIR SYNTHESIS<br/>[FR] DÉRIVÉS DE LUCIFÉRINE ET LEURS PROCÉDÉS DE SYNTHÈSE
  申请人：UNIV CAPE TOWN

  公开号：WO2019021202A1

  公开（公告）日：2019-01-31

  6-Thio derivatives of D-luciferin, also referred to as D-thioluciferins, having the general structure of Formula (I) are provided. Methods for synthesising D-luciferin, its derivatives, and their related 2-cyanobenzothiazole precursors are also provided. These compounds are commercially valuable due to their application in optical imaging, particularly in bioluminescence imaging.

  提供了D-荧光素的6-硫代衍生物，也称为D-硫代荧光素，其一般结构如下所示的公式（I）。还提供了合成D-荧光素、其衍生物以及它们相关的2-氰基苯并噻唑前体的方法。这些化合物在光学成像中具有商业价值，特别是在生物发光成像中。
• Novel 6-substituted benzothiazol-2-yl indolo[1,2-c]quinazolines and benzimidazo[1,2-c]quinazolines
  作者：Stéphane Frère、Valérie Thiéry、Christian Bailly、Thierry Besson

  DOI：10.1016/s0040-4020(02)01593-4

  日期：2003.2

  The synthetic route to and a preliminary biological evaluation of novel indolo[1,2-c]quinazolines (8) and benzimidazo[1,2-c]quinazolines (9) are described. The products were obtained by condensation of the appropriate diamines (e.g. 2-(2-aminophenyl)indole or 2-(2-aminophenyl)benzimidazole) with 2-cyanobenzothiazoles. This work further demonstrates the general applicability of microwaves for a facile

  描述了合成吲哚[1,2- c ]喹唑啉（8）和苯并咪唑并[1,2- c ]喹唑啉（9）的合成途径和初步生物学评价。通过适当的二胺（例如2-（2-氨基苯基）吲哚或2-（2-氨基苯基）苯并咪唑）与2-氰基苯并噻唑的缩合获得产物。这项工作进一步证明了微波的普遍适用性，可以轻松快速地获得具有潜在药物价值的原始杂环。
• Aniline derivatives having herbicidal activity, their preparation and
  申请人：Sankyo Company, Limited

  公开号：US05736487A1

  公开（公告）日：1998-04-07

  Compounds of formula (I): ##STR1## (wherein: R.sup.1 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy, or optionally substituted alkylthio; R.sup.2 is hydrogen, optionally substituted alkyl, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or a group of formula --YR.sup.7 ; R.sup.3 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro or a group of formula --COR.sup.8, wherein R.sup.8 is hydrogen, alkyl, cycloalkyl or alkoxy; R.sup.4 and R.sup.5 are each hydrogen atom or alkyl; R.sup.6 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro, or a group of formula --COR.sup.8, as defined above; A, Q and X are each oxygen or sulfur; Y is a group of formula --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.2 S--, --CH.sub.2 CO--, --CH.sub.2 COO--, --CH(Me)COO--, --CH.sub.2 CH.sub.2 CO--, --CH.sub.2 OCO--, CH.sub.2 OCOO-- and --CH.sub.2 CH.sub.2 OCO--; R.sup.7 is optionally substituted alkyl group, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted aralkyl, or an optionally substituted heterocycle; and m and n are each an integer from 0 to 4; and herbicidally acceptable addition salts thereof) are useful as herbicides.

  式(I)的化合物：##STR1##（其中：R.sup.1是可选取代的烷基，环烷基，可选取代的烷氧基或可选取代的烷硫基; R.sup.2是氢，可选取代的烷基，环烷基，可选取代的烯基，可选取代的炔基或式--YR.sup.7的基团; R.sup.3是可选取代的烷基，环烷基，可选取代的烷氧基，可选取代的烯基，可选取代的炔基，卤素，硝基或式--COR.sup.8的基团，其中R.sup.8是氢，烷基，环烷基或烷氧基; R.sup.4和R.sup.5分别是氢原子或烷基; R.sup.6是可选取代的烷基，环烷基，可选取代的烷氧基，可选取代的烯基，可选取代的炔基，卤素，硝基或式如上所定义的--COR.sup.8的基团; A，Q和X分别是氧或硫; Y是式--CO--，--COO--，--CH.sub.2 O--，--CH.sub.2 S--，--CH.sub.2 CH.sub.2 O--，--CH.sub.2 CH.sub.2 S--，--CH.sub.2 CO--，--CH.sub.2 COO--，--CH(Me)COO--，--CH.sub.2 CH.sub.2 CO--，--CH.sub.2 OCO--，CH.sub.2 OCOO--和--CH.sub.2 CH.sub.2 OCO--的基团; R.sup.7是可选取代的烷基，环烷基，可选取代的烯基，可选取代的炔基，可选取代的芳基，可选取代的芳基烷基或可选取代的杂环基; m和n分别是从0到4的整数;以及其除草剂可接受的盐)可用作除草剂。
• BIOLUMINESCENT ASSAYS USING CYANOBENZOTHIAZOLE COMPOUNDS
  申请人：Kelts Jessica

  公开号：US20110223625A1

  公开（公告）日：2011-09-15

  The invention provides methods that employ derivatives of 2-cyano-6-hydroxy- or 2-cyano-6-amino-benzothiazole, for example, in a bioluminogenic reaction. The invention further provides methods for detecting or determining the presence of molecules and/or enzymes, the modulator activity of such molecules, and/or the activity of such enzymes. The methods are adaptable to high-throughput format.

  该发明提供了使用2-氰基-6-羟基或2-氰基-6-氨基苯并噻唑的衍生物的方法，例如在生物发光反应中使用。该发明还提供了用于检测或确定分子和/或酶的存在，这些分子的调节活性和/或这些酶的活性的方法。这些方法可适应于高通量格式。