5,6-二氢-3-苯基咪唑并[2,1-b]噻唑 | 36065-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 中文名称: 5,6-二氢-3-苯基咪唑并[2,1-b]噻唑
• 英文名称: 3-phenyl-5,6-dihydro-imidazo[2,1-b]thiazole
• 英文别名: 3-Phenyl-5,6-dihydro-imidazo[2,1-b]thiazol；Imidazo(2,1-b)thiazole, 5,6-dihydro-3-phenyl-；3-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole
• CAS: 36065-41-5
• 化学式: C₁₁H₁₀N₂S
• 分子量: 202.28
• InChiKey: OZNXXVWKDIUAJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  5,6-二氢-3-苯基咪唑并[2,1-b]噻唑 在 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 7.0h， 生成 1H-吡咯并[1,2-a]咪唑-5,7-二羧酸,1-[2-[(3-乙氧基-3-羰基-1-丙烯基)硫代]-1-苯基乙烯基]-2,3-二氢-,二乙基酯,(E,Z)-
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of 5,6-dihydroimidazo[2,1-b]thiazolium betaines

  摘要：

  5,6-Dihydroimidazo[2,1-b]thiazolium betaines were generated in situ from 3,7-disubstituted 5,6-dihydroimidazo[2,1-b]thiazolium bromides and triethylamine. The reaction of these imidazothiazolium betaines with acetylenic dipolarophiles, such as ethyl propiolate, dimethyl acetylenedicarboxylate, and dibenzoylacetylene, provided geometric cis,trans isomers containing 2,3-dihydro-1H-pyrrolo[1,2-a]imidazole. We have proposed a mechanism of this reaction that involves 1,3-dipolar cycloaddition, isomeric rearrangement, and then nucleophilic addition successively. The ratio of trans and cis isomers depended on the temperature and solvents. The stereoselectivity of trans isomers increased with increasing temperature and decreasing polarity of solvents.

  DOI：

  10.1021/jo00034a029
• 作为产物：
  描述：

  3-phenyl-5,6-dihydroimidazo<2,1-b>thiazole hydrobromide 生成 5,6-二氢-3-苯基咪唑并[2,1-b]噻唑
  参考文献：
  名称：

  Acheson, R. Morrin; Cooper, Martin W.; Cox, Ian R., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1773 - 1778

  摘要：

  DOI：

文献信息

• Structure–activity relationship of dihydroimidazo-, dihydropyrimido, tetrahydrodiazepino-[2,1-b]-thiazoles, and -benzothiazoles as an acylation catalyst
  作者：Sentaro Okamoto、Yuzo Sakai、Saki Watanabe、Shohei Nishi、Aya Yoneyama、Hitomi Katsumata、Yu Kosaki、Rumi Sato、Megumi Shiratori、Misuzu Shibuno、Tsukasa Shishido

  DOI：10.1016/j.tetlet.2014.01.135

  日期：2014.3

  synthesized by a condensation reaction of cyclic thioureas 15 and α-bromoacetophenones 14. Investigations of the acylation reactions of 1-phenylethanol with acid anhydrides in the presence of these cyclic isothiourea catalysts revealed their structure–activity relationships. Remarkable electronic effects resulting from substituent(s) on a benzo or phenyl moiety and the influence of the size of the annulating

  环状异硫脲1，2，3，和4通过一个四步骤程序由相应的合成邻-bromoanilines 10经由Pd或铜催化的环化-苯并噻唑形成。Nonbenzo类似物7，8，和9通过循环硫脲的缩合反应合成的15和α-bromoacetophenones 14。在这些环状异硫脲催化剂的存在下，对1-苯乙醇与酸酐的酰化反应的研究表明了它们的结构活性关系。观察到由苯并或苯基部分上的一个或多个取代基引起的显着电子效应以及环环尺寸的影响。供电子取代基的引入提高了反应速率。还研究了对3型和7型手性催化剂的一些取代作用。
• Solid state synthesis of 2-aroylbenzo[b]furans, 1,3-thiazoles and 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles from α-tosyloxyketones using microwave irradiation †
  作者：Rajender S. Varma、Dalip Kumar、Per J. Liesen

  DOI：10.1039/a807563h

  日期：——

  3]thiazoles are described from readily accessible α-tosyloxyketones and mineral oxides in processes that are accelerated by exposure to microwaves. The 2-aroylbenzo[b]furans are readily obtained from salicylaldehydes and α-tosyloxyketones in the presence of solid potassium fluoride doped alumina (KF–Al2O3) whereas montmorillonite K-10 clay provides 1,3-thiazoles from thioamides and α-tosyloxyketones

  2-芳酰基苯并的迅速无溶剂合成[ b ]呋喃，1,3-噻唑和3-芳基-5,6-二氢咪唑并[2,1- b ] [1,3]是从容易获得α-tosyloxyketones描述噻唑类和通过暴露于微波而加速的过程中的矿物氧化物。在固态氟化钾掺杂的氧化铝（KF–Al 2 O 3）存在下，从水杨醛和α-甲苯磺酰氧基酮很容易获得2-芳基苯并[ b ]呋喃，而蒙脱土K-10粘土从硫酰胺和α提供了1,3-噻唑。 -甲苯磺酰氧基酮。同样，亚乙基硫脲和α-甲苯磺酰氧基酮可提供桥头氮杂环，3-芳基-5,6-二氢咪唑并[2,1- b] [1,3]噻唑类，其收率很高，在传统的加热条件下不易获得。
• Phenacylthioimidazolines and 3-aryl-5,6-dihydroimidazo[2,1-b]thiazoles with antidepressant activity
  作者：C. J. Sharpe、R. S. Shadbolt、A. Ashford、J. W. Ross

  DOI：10.1021/jm00292a023

  日期：1971.10
• Dramatic Acceleration of an Acyl Transfer-Initiated Cascade by Using Electron-Rich Amidine-Based Catalysts
  作者：Nicholas A. Ahlemeyer、Emma V. Streff、Pandi Muthupandi、Vladimir B. Birman

  DOI：10.1021/acs.orglett.7b03044

  日期：2017.12.15

  A tandem rearrangement of alpha,beta-unsaturated, thioesters into tricyclic ene-lactones fails with conventional amidine-based catalysts, but becomes possible when their electron-rich analogs are employed. A highly diastereo- and enantioselective version of this process has been developed using H-PIP 1b, a chiral catalyst prepared over a decade ago, but never utilized since its disclosure.
• 4′: 5′-Dihydroglyoxalino(2′: 1′- 2: 3)thiazolium salts, and the ultraviolet light absorption of thiazole derivatives
  作者：Walter Wilson、R. Woodger

  DOI：10.1039/jr9550002943

  日期：——