(Z)-3-benzylidene-1-methyl-1,3-dihydro-benzo[c]isothiazole-2,2-dioxide

• 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: (Z)-3-benzylidene-1-methyl-1,3-dihydro-benzo[c]isothiazole-2,2-dioxide
• 英文别名: (3Z)-3-benzylidene-1-methyl-2,1-benzothiazole 2,2-dioxide
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: RUKCZOOQNQRYBQ-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-benzylidene-1-methyl-1,3-dihydro-benzo[c]isothiazole-2,2-dioxide 、 4-methoxy-N'-phenylbenzohydrazonoyl chloride 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以83%的产率得到5-(2-methylaminophenyl)-1,4-diphenyl-3-(4-methoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  Cascade 1,3-dipolar Cycloaddition/SO2 extrusion approach for the rapid synthesis of tetraaryl-substituted pyrazoles with Aggregation Induced Emission characteristics

  摘要：

  A highly efficient strategy was developed for the straightforward synthesis of tetraaryl-substituted pyrazoles. The cascade process consists of a regioselective 1,3-dipolar cycloaddition of benzosultam-3-ylidenes with nitrile imines and a subsequent elimination of SO2. The title compounds exhibit high fluorescence quantum yields and Aggregation Induced Emission (AIE) characteristics. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131568
• 作为产物：
  描述：

  N-(2-溴苯基)甲烷磺酰胺 在 sodium hydride 、 potassium carbonate 、 sodium amide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (Z)-3-benzylidene-1-methyl-1,3-dihydro-benzo[c]isothiazole-2,2-dioxide
  参考文献：
  名称：

  1,3-偶极环苯并异噻唑-2,2-二氧化物-3-亚烷基和偶氮甲亚胺内酯的1,3-偶极环加成反应合成螺并吡咯烷基-苯并异噻唑啉衍生物

  摘要：

  新的螺环化合物螺吡咯​​烷基-苯并异噻唑啉衍生物是通过苯并异噻唑-2,2-二氧化物-3-亚烷基的1,3-偶极环加成反应和偶氮亚甲基叶立德合成的。研究了1,3-偶极环加成反应的立体化学以及苯并异噻唑-2,2-二氧化物与醛的Knoevenagel缩合反应的立体化学。

  DOI：

  10.1016/j.tet.2014.10.039

文献信息

• Synthesis of 3,4,5-trisubstituted isoxazoles via 1,3-dipolar cycloaddition/SO₂ extrusion of benzoisothiazole-2,2-dioxide-3-ylidenes with nitrile oxides
  作者：Guorui Cao、Yu Wang、Tao Cui、Longjiang Huang、Dawei Teng

  DOI：10.1039/c5ra26718h

  日期：——

  synthesis of 3,4,5-trisubstituted isoxazole derivatives via 1,3-dipolar cycloaddtion/SO2 extrusion of benzoisothiazole-2,2-dioxide-3-ylidenes with nitrile oxides is reported using 4 Å molecular sieves as a dehydrochlorinating agent. This tandem ring closing/ring opening synthesis of 3,4,5-trisubstituted isoxazoles is the first of its kind. This methodology would enrich the synthetic chemistry of isoxazoles

  据报道，使用4Å分子筛作为脱氯化氢试剂，通过1,3-偶极环加成/ SO 2挤出苯并异噻唑-2,2-二氧化物-3-亚烷基与腈类化合物直接合成3,4,5-三取代异恶唑衍生物。。这种串联的3,4,5-三取代的异恶唑的开环/开环合成方法尚属首次。该方法将丰富易得原料的异恶唑的合成化学，并有利于发现具有潜在生物活性的新型异恶唑。
• Cascade 1,3-dipolar Cycloaddition/SO2 extrusion approach for the rapid synthesis of tetraaryl-substituted pyrazoles with Aggregation Induced Emission characteristics
  作者：Guorui Cao、Xiang Liu、Long Wang、Yanshun Li、Dawei Teng

  DOI：10.1016/j.tet.2020.131568

  日期：2020.10

  A highly efficient strategy was developed for the straightforward synthesis of tetraaryl-substituted pyrazoles. The cascade process consists of a regioselective 1,3-dipolar cycloaddition of benzosultam-3-ylidenes with nitrile imines and a subsequent elimination of SO2. The title compounds exhibit high fluorescence quantum yields and Aggregation Induced Emission (AIE) characteristics. (C) 2020 Elsevier Ltd. All rights reserved.
• Synthesis of spiropyrrolidinyl-benzoisothiazoline derivatives by 1,3-dipolar cycloaddition of benzoisothiazole-2,2-dioxide-3-ylidenes and azomethine ylide
  作者：Guorui Cao、Feifei Long、Yingchun Zhao、Yu Wang、Longjiang Huang、Dawei Teng

  DOI：10.1016/j.tet.2014.10.039

  日期：2014.12

  The new spirocyclic compounds, spiropyrrolidinyl-benzoisothiazoline derivatives were synthesized by the 1,3-dipolar cycloaddition of benzoisothiazole-2,2-dioxide-3-ylidenes and azomethine ylide. The stereochemistry of 1,3-dipolar cycloaddition as well as the stereochemistry of Knoevenagel condensation of benzoisothiazole-2,2-dioxide with aldehydes were studied.

  新的螺环化合物螺吡咯​​烷基-苯并异噻唑啉衍生物是通过苯并异噻唑-2,2-二氧化物-3-亚烷基的1,3-偶极环加成反应和偶氮亚甲基叶立德合成的。研究了1,3-偶极环加成反应的立体化学以及苯并异噻唑-2,2-二氧化物与醛的Knoevenagel缩合反应的立体化学。