3-(4-(4-methoxybenzyl)-1-piperazinyl)-1,2-benzisothizole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(4-(4-methoxybenzyl)-1-piperazinyl)-1,2-benzisothizole
• 英文别名: 3-[4-(4-Methoxyphenyl)piperazin-1-yl]-1,2-benzothiazole
• 化学式: C₁₈H₁₉N₃OS
• 分子量: 325.434
• InChiKey: QPDHHCYMYILIJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲亚胺酸乙酯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 silver(I) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 3-(4-(4-methoxybenzyl)-1-piperazinyl)-1,2-benzisothizole
  参考文献：
  名称：

  Synthesis of Isothiazoles and Isoselenazoles through Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur and Selenium

  摘要：

  A rhodium-catalyzed oxidative annulation of benzimidates with elemental sulfur for the direct construction of isothiazole rings is reported. The proposed reaction mechanism involving Rh(I)/Rh(III) redox is supported by a stoichiometric reaction of metallacycle species as well as DFT calculations. This method is also applicable to selenium cyclization to produce isoselenazole derivatives. The alkoxy substituent at C3 can be used for further functionalization of the azole core.

  DOI：

  10.1021/acs.orglett.0c03674

文献信息

• Synthesis of Isothiazoles and Isoselenazoles through Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur and Selenium
  作者：Sanghun Moon、Yuji Nishii、Masahiro Miura

  DOI：10.1021/acs.orglett.0c03674

  日期：2021.1.1

  A rhodium-catalyzed oxidative annulation of benzimidates with elemental sulfur for the direct construction of isothiazole rings is reported. The proposed reaction mechanism involving Rh(I)/Rh(III) redox is supported by a stoichiometric reaction of metallacycle species as well as DFT calculations. This method is also applicable to selenium cyclization to produce isoselenazole derivatives. The alkoxy substituent at C3 can be used for further functionalization of the azole core.