4-(bromomethyl)-4-methyl-2-phenyl-4,5-dihydrothiazole | 1581730-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(bromomethyl)-4-methyl-2-phenyl-4,5-dihydrothiazole
• 英文别名: 4-(bromomethyl)-4-methyl-2-phenyl-5H-1,3-thiazole
• CAS: 1581730-89-3
• 化学式: C₁₁H₁₂BrNS
• 分子量: 270.193
• InChiKey: CEBGVCPGIPEEHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(bromomethyl)-4-methyl-2-phenyl-4,5-dihydrothiazole 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 以81%的产率得到4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrothiazole
  参考文献：
  名称：

  Synthesis of Thiazolines by Copper Catalyzed Aminobromination of Thiohydroximic Acids

  摘要：

  A copper catalyzed aminobromination of Alkene tethered thiohydroximic acids is described, providing a rapid approach to unnatural thiazoline scaffolds not readily available via existing methods. Moderate to high yields of bromothiazolines are obtained with alkyl- and aryl-substituted thiohydroximic acid building blocks containing mono-, di-, and trisubstituted alkenes. The reaction provides high levels of 5-exo selectivity, and terminally monosubstituted alkenes result in predominant syn-diastereoselectivity.

  DOI：

  10.1021/ol500588v
• 作为产物：
  描述：

  2-methylallyl N-benzoyloxybenzimidothioate 在 copper(I) bromide dimethylsulfide complex 、 lithium bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以23%的产率得到4-(bromomethyl)-4-methyl-2-phenyl-4,5-dihydrothiazole
  参考文献：
  名称：

  Synthesis of Thiazolines by Copper Catalyzed Aminobromination of Thiohydroximic Acids

  摘要：

  A copper catalyzed aminobromination of Alkene tethered thiohydroximic acids is described, providing a rapid approach to unnatural thiazoline scaffolds not readily available via existing methods. Moderate to high yields of bromothiazolines are obtained with alkyl- and aryl-substituted thiohydroximic acid building blocks containing mono-, di-, and trisubstituted alkenes. The reaction provides high levels of 5-exo selectivity, and terminally monosubstituted alkenes result in predominant syn-diastereoselectivity.

  DOI：

  10.1021/ol500588v

文献信息

• Synthesis of Quaternary-Substituted Thiazolines via Halocyclization of <i>S</i>-Allyl Thioimidate Salts
  作者：Patrick D. Parker、Bérénice C. Lemercier、Joshua G. Pierce

  DOI：10.1021/acs.joc.7b02299

  日期：2018.1.5

  described. A range of mono-, di-, and trisubstituted olefins as well as alkyl- and arylthioamides with variations in electronics are tolerated. A rapid anti-diastereoselective halocyclization of these salts provides a variety of substituted alkyl- and arylthiazolines. Initial development of an efficient enantioselective synthesis of quaternary-substituted thiazolines through the organo-catalyzed halocyclization

  描述了通过硫代酰胺与烯丙基溴衍生物的偶联有效合成S-烯丙基硫代亚氨酸氢溴酸盐的方法。容许一系列在电子学上有所变化的单，二和三取代的烯烃以及烷基和芳基硫代酰胺。这些盐的快速抗-非对映选择性卤环化提供了各种取代的烷基-和芳基噻唑啉。还描述了通过有机催化的磺酸盐硫代亚氨酸盐的卤代环化反应来有效地合成季取代的噻唑啉的对映体。
• Synthesis of Thiazolines by Copper Catalyzed Aminobromination of Thiohydroximic Acids
  作者：Bérénice C. Lemercier、Joshua G. Pierce

  DOI：10.1021/ol500588v

  日期：2014.4.4

  A copper catalyzed aminobromination of Alkene tethered thiohydroximic acids is described, providing a rapid approach to unnatural thiazoline scaffolds not readily available via existing methods. Moderate to high yields of bromothiazolines are obtained with alkyl- and aryl-substituted thiohydroximic acid building blocks containing mono-, di-, and trisubstituted alkenes. The reaction provides high levels of 5-exo selectivity, and terminally monosubstituted alkenes result in predominant syn-diastereoselectivity.