2-(1,2-dimethoxyethyl)benzo[d]thiazole | 1332362-53-4

• 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: 2-(1,2-dimethoxyethyl)benzo[d]thiazole
• 英文别名: 2-(1,2-Dimethoxyethyl)-1,3-benzothiazole
• CAS: 1332362-53-4
• 化学式: C₁₁H₁₃NO₂S
• 分子量: 223.296
• InChiKey: CZOHXGNYQGYTDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙二醇二甲醚 、 (2-isocyanophenyl)(methyl)sulfane 在 2,4,5,6-四(9H-咔唑-9-基)异酞腈 作用下， 反应 24.0h， 以34%的产率得到2-(1,2-dimethoxyethyl)benzo[d]thiazole
  参考文献：
  名称：

  Visible Light‐Induced Metal‐Free and Oxidant‐Free Radical Cyclization of (2‐Isocyanoaryl)(methyl)sulfanes with Ethers

  摘要：

  AbstractA novel cascade cyclization of (2‐isocyanoaryl) (methyl)sulfanes and ethers is developed. With 4CzIPN as a photocatalyst and the irradiation of blue LED light, ether radicals are efficiently generated without adding any oxidant, endowing the strategy with features of oxidant‐free, metal‐free, mild reaction conditions, and operational simplicity. This strategy provides efficient approach to access various ether‐containing benzothiazoles in acceptable to good yields.

  DOI：

  10.1002/ejoc.202100501

文献信息

• Iron-catalyzed direct α-arylation of ethers with azoles
  作者：Arkaitz Correa、Béla Fiser、Enrique Gómez-Bengoa

  DOI：10.1039/c5cc05005g

  日期：——

  The direct α-arylation of cyclic and acyclic ethers with azoles has been achieved, which features a novel iron-catalyzed cross-dehydrogenative coupling (CDC) process.

  环状和非环状醚与唑类化合物的直接α-芳基化已经实现，其中包括一种新颖的铁催化的交叉脱氢偶联（CDC）过程。
• Direct C2-Alkylation of Azoles with Alcohols and Ethers through Dehydrogenative Cross-Coupling under Metal-Free Conditions
  作者：Tao He、Lin Yu、Lei Zhang、Lei Wang、Min Wang

  DOI：10.1021/ol201779n

  日期：2011.10.7

  metal-free novel, simple, and highly efficient method for the direct C2-alkylation of azoles with alcohols and ethers has been developed on the basis of an oxidative C–H activation process. The dehydrogenative C–C cross-coupling reactions of α-position sp3 C–H in alcohols and ethers with the 2-position sp2 C–H in azoles proceeded smoothly in the presence of tert-butyl hydroperoxide (TBHP) under neat reaction

  在氧化CH活化过程的基础上，开发了一种无金属的新颖，简单，高效的方法，用于将唑类与醇和醚直接进行C2-烷基化反应。在叔丁基过氧化氢（TBHP）存在下，在纯净反应下，醇和醚中的α-位置sp 3 C-H与唑类中的2-位sp 2 C-H的脱氢CC交叉偶联反应顺利进行条件下，产生相应产物的收率很高。
• Photoredox-Mediated Direct Cross-Dehydrogenative Coupling of Heteroarenes and Amines
  作者：Jianyang Dong、Qing Xia、Xueli Lv、Changcun Yan、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.8b02389

  日期：2018.9.21

  A photoredox-mediated direct cross-dehydrogenative coupling reaction to accomplish α-aminoalkylation of N-heteroarenes is reported. This mild reaction has a broad substrate scope, offers the first general method for synthesis of aminoalkylated N-heteroarenes without the need for substrate prefunctionalization, and is scalable to the gram level. Furthermore, the reaction was found to be applicable to

  报道了光氧化还原介导的直接交叉脱氢偶联反应以完成N-杂芳烃的α-氨基烷基化。这种温和的反应具有广泛的底物范围，提供了无需进行底物预官能化即可合成氨基烷基化N-杂芳烃的第一种通用方法，并且可扩展至克级。此外，发现该反应除了胺（即，醚，醛，甲酰胺，对二甲苯和烷烃）以外还适用于其他氢供体，因此能够制备带有各种取代基的N-杂芳烃。