3-octyloxy-1,2-benzisothiazole | 1351520-93-8

• 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: 3-octyloxy-1,2-benzisothiazole
• 英文别名: 3-(octyloxy)benzo[d]isothiazole；3-octyloxybenzisothiazole；3-octoxy-1,2-benzothiazole
• CAS: 1351520-93-8
• 化学式: C₁₅H₂₁NOS
• 分子量: 263.404
• InChiKey: IKXQBUZVVHLGKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  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， 反应 23.0h， 以87%的产率得到3-octyloxy-1,2-benzisothiazole
  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

• Benzisothiazolinone as a useful template for the design of new monoacylglycerol lipase inhibitors: Investigation of the target residues and comparison with octhilinone
  作者：Nicolas Matuszak、Bouazza Es Saadi、Geoffray Labar、Jacqueline Marchand-Brynaert、Didier M. Lambert

  DOI：10.1016/j.bmcl.2011.10.026

  日期：2011.12

  The regulation of 2-arachidonoylglycerol (2-AG) levels is a major issue as 2-AG has been proven to participate in numerous physiopathological phenomena such as neuroprotection or analgesia. Octhilinone, a cysteine-reagent compound, has recently been shown to inhibit in the nanomolar range monoacylglycerol lipase (MAGL), the major enzyme responsible for the degradation of 2-AG. Here, we further investigate the mechanism by which octhilinone and its benzisothiazolinone analog inhibit human MAGL. We also provide new information on the structural requirements for MAGL inhibition by these compounds. Finally, we describe for N-octylbenzisothiazolinone a mode of inhibition which is partially different from that described for octhilinone, especially with regard to the targeted cysteine residues in the vicinity of the catalytic site. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.