benzothiazole-2-ylmagnesium chloride | 126507-54-8

• 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: benzothiazole-2-ylmagnesium chloride
• 英文别名: 2-benzothiazolylmagnesium chloride；Benzothiazol-2-yl-magnesiumchlorid
• CAS: 126507-54-8
• 化学式: C₇H₄ClMgNS
• 分子量: 193.939
• InChiKey: RKKGWSLOGVJXNP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-碘三氟甲苯 、 benzothiazole-2-ylmagnesium chloride 在 lithium chloro-isopropyl-magnesium chloride 、 tbepc 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到2-[3-(三氟甲基)苯基]-1,3-苯并噻唑
  参考文献：
  名称：

  铁利用氧作为氧化剂催化N-杂芳基和芳基金属试剂的氧化组装。

  摘要：

  在等量的钛酸酯介导之后，在FeCl3 / TMEDA的催化下，在室温下使用氧气作为氧化剂，将等量的N-杂芳基和芳基格氏试剂或锂试剂轻松偶联以提供N-杂芳基-芳基化合物。大多数常见的N-杂芳基都是很好的候选物，因此为各种N-杂芳基-芳基结构的灵活构建提供了通用，绿色和实用的方案。

  DOI：

  10.1039/c4cc08494b

文献信息

• A new synthesis of chloroheterocycles via metalhalogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents
  作者：Carla Boga、Erminia Del Vecchio、Luciano Forlani、Lilia Milanesi、Paolo Edgardo Todesco

  DOI：10.1016/s0022-328x(99)00363-0

  日期：1999.10

  rapidly produces the corresponding 2-chloro derivatives in high yields through a metalhalogen exchange mechanism. The use of ethyl trichloroacetate can give better results with respect to those obtained with trichloroacetyl chloride, which probably involves dichloroketene formation. The reaction with Grignard reagents is more complex: in fact, 2-benzothiazolylmagnesium chloride with ethyl trichloroacetate

  芳族氮杂杂环的2-lithio衍生物与三氯乙酰基衍生物之间的反应通过金属-卤素交换机理快速高产地产生了相应的2-氯衍生物。与用三氯乙酰氯得到的三氯乙酸乙酯相比，使用三氯乙酸乙酯可以得到更好的结果，三氯乙酰氯可能涉及二氯乙烯的形成。与格氏试剂的反应更加复杂：实际上，2-苯并噻唑基氯化镁与三氯乙酸乙酯或三氯乙酰氯的反应分别生成2-氯苯并噻唑和大量的1,3-苯并噻唑-2-羧酸乙酯或2-苯并噻唑基二氯甲基酮。
• Methodology for the Preparation of 2-Argininylbenzothiazole
  作者：Birdella D. Kenney、Michael Breslav、Rosie Chang、Roland Glaser、Bruce D. Harris、Cynthia A. Maryanoff、John Mills、Armin Roessler、Brigitte Segmuller、Frank J. Villani

  DOI：10.1021/jo7019543

  日期：2007.12.1

  [Graphics]An efficient process to produce kilogram quantities of a key, argininylbenzo[d]thiazole intermediate was developed for the preparation of the tryptase inhibitor RWJ-56423. A variety of activated arginine esters and benzo[d]thiazole nucleophiles were evaluated as coupling partners. Our work led to the selection and optimization of an argininyl imidazolide ester and benzothiazol-2-yl MgCl nucleophile. This paper focuses on the preparation, use, and stability of the benzothiazol-2-yl Grignard reagents.
• Synthesis of the first representative of dicarbothiacyanine dyes with completely fluorinated polymethine chain
  作者：Lev M. Yagupolskii、Оksana I. Chernega、Nataliya V. Kondratenko、Alexander N. Chernega、Yurii. G. Vlasenko、Ruslan V. Nedelkov、Yurii L. Yagupolskii

  DOI：10.1016/j.jfluchem.2009.11.012

  日期：2010.2

  2-Iodobenzothiazole was reacted with tributyl(pentafluorobutadienyl)tin in the Stille reaction conditions to give 2-pentafluorobutadienylbenzothiazole 1. The quaternary salt of 1 via interaction with 2-fluoromethylbenzothiazole methylene base, obtained in situ, forms two cyanine dyes 8 and 9 as a result of nucleophilic attack of two different positions of perfluorobutadiene chain. The pure 2-fluoromethylbenzothiazole methylene base (in a dimer form) was obtained by deprotonation of the corresponding salt by NaH and on reacting with I forms the dye base 11 that underwent electrocyclization and subsequent HF addition to form the cyclohexadiene 12 identified by X-ray analysis data. Upon quaternization and HF abstraction by toluidine the recyclization occurred and dye 8 - the first representative of dicarbothiacyanine dyes with perfluorinated polymethine chain - was obtained. It has lambda(max) = 691 nm, that is 41 nm more than in non fluorinated dye, vinylene shift is equal to 111 nm. (C) 2009 Elsevier B.V. All rights reserved.