8-(1-naphthyl)-5,5-dioxo-1-aza-2-oxa-5-thiabicyclo<3.2.1>octane | 122603-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 8-(1-naphthyl)-5,5-dioxo-1-aza-2-oxa-5-thiabicyclo<3.2.1>octane
• 英文别名: 8-(1-naphthyl)-5,5-dioxo-1-aza-2-oxa-5-thiabicyclo[3.2.1]octane
• CAS: 122603-50-3
• 化学式: C₁₅H₁₅NO₃S
• 分子量: 289.355
• InChiKey: DQCLNYRPFNBBMZ-CABCVRRESA-N

物化性质

• 熔点：
  146-148 °C
• 沸点：
  537.9±60.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  二乙烯基砜 、 1-naphtylaldehyde oxime 生成 8-(1-naphthyl)-5,5-dioxo-1-aza-2-oxa-5-thiabicyclo<3.2.1>octane
  参考文献：
  名称：

  肟与乙烯基砜的分子内环加成反应

  摘要：

  肟与含有π键的乙烯基砜反应生成环加合物，该环加合物衍生自瞬态腈的分子内偶极环加成。

  DOI：

  10.1016/s0040-4039(00)87896-x

文献信息

• 7-Oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-Dioxides: Mechanochemical Synthesis by Tandem Michael Addition-1,3-Dipolar Cycloaddition of Aldoximes and Evaluation of Antibacterial Activities
  作者：Zigmee T. Bhutia、Avijit Das、Malabika Biswas、Amrita Chatterjee、Mainak Banerjee

  DOI：10.1002/ejoc.201701511

  日期：2018.1.31

  2.1]octane-4,4-dioxide derivatives in good overall yields. The newly synthesized bicyclo aza-sulfone derivatives (4) were screened for antibacterial activities. It was found that mostly bicyclo aza-sulfones derived from electron rich aromatic aldehydes inhibit the growth of Mycobacterium smegmatis (mc2-155) and that of aliphatic aldehydes inhibit the growth of Escherichia coli (DH5a) in moderate to

  一种用于合成一系列桥连双环氮杂砜衍生物的无溶剂、绿色、高效的机械化学方法。7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane-4,4-dioxides 通过醛肟的串联迈克尔加成-1,3-偶极环加成得到了开发。机械化学研磨/研磨有助于从相应的醛和羟胺快速形成醛肟，在混合研磨机中与二乙烯基砜反应后得到 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane-4,4-总体收率良好的二氧化物衍生物。筛选了新合成的双环氮杂砜衍生物 (4) 的抗菌活性。发现大多数源自富电子芳香醛的双环氮杂砜抑制耻垢分枝杆菌 (mc2-155) 的生长，脂肪醛抑制大肠杆菌 (DH5a) 的生长，效果中等至良好。然而，发现丁醛衍生的化合物 4r 对耻垢分枝杆菌和大肠杆菌都非常有效。这种机械化学方法的主要优点是无催化剂和溶剂条件，反应时间更短，以及新系列的 7-oxa-4
• Tandem addition-cycloaddition reaction of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene as a method for 4-piperidone synthesis
  作者：Bryan H. Norman、Yves Gareau、Albert Padwa

  DOI：10.1021/jo00006a036

  日期：1991.3

  The reaction of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene affords 7-oxa-1-azanorbornanes in high yield. The formation of the bicyclic isoxazolidine involves conjugate addition of the oxime onto the diene to give a transient nitrone that then undergoes a subsequent intramolecular dipolar cycloaddition reaction. The coupling of several oximes with divinyl sulfone was also studied, and related cycloadducts were obtained in excellent yield. The stereochemistry of the cycloaddition is best explained in terms of an exclusive reaction of the Z isomer of the nitrone via an easily attainable endo orientation of the reactive groups. Molecular mechanics calculations have been refined to accurately predict the regiochemistry of the intramolecular cycloaddition. Treatment of these 7-oxa-1-azanorbornanes with Raney nickel in methanol results in reductive nitrogen-oxygen bond cleavage to give substituted 4-piperidones. The bicyclic isoxazolidine derived from cyclohexanone oxime and bis(phenyl-sulfonyl)diene was converted to the azaspiro[5.5]undecane ring system, which is representative of the key ring skeleton of the perhydrohistrionicotoxin family of alkaloids.