4-Thia-2,6-diazatricyclo<5.2.2.0>undecane-3,5-dione | 41316-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-Thia-2,6-diazatricyclo<5.2.2.0>undecane-3,5-dione
• 英文别名: 4-thia-2,6-diazatricyclo[5.2.2.0^2,6]undecane-3,5-dione；5,6,7,8-tetrahydro-5,8-ethano-[1,3,4]thiadiazolo[3,4-a]pyridazine-1,3-dione；2,3-diaza-bicyclo[2.2.2]octane-2,3-dicarboxylic acid thioanhydride；4-Thia-2,6-diazatricyclo[5.2.2.02,6]undecane-3,5-dione
• CAS: 41316-20-5
• 化学式: C₈H₁₀N₂O₂S
• 分子量: 198.246
• InChiKey: RSSRDSVVMZDXGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Thia-2,6-diazatricyclo<5.2.2.0>undecane-3,5-dione 以 氘代甲醇 为溶剂， 反应 0.25h， 以100%的产率得到7,8-二氮杂双环[2.2.2]辛-7-烯
  参考文献：
  名称：

  1-Thia-3,4-diazolidine-2,5-dione functionality: a photochemical synthon for the azo group

  摘要：

  The 1-thia-3,4-diazolidine-2,5-dione functional group was shown to yield azo compounds upon photolysis. This photoreaction when combined with the known ability of this group to react in a Diels-Alder fashion or as a dinucelophile toward alkylating agents greatly increases the utility of this functionality. The dual reactivity of this group was demonstrated in the synthesis of a number of 3,4-dialkyl-1-thia-3,4-diazolidine-2,5-diones. The photolysis of these compounds produced either thermally stable cyclic azo compounds or the decomposition products of thermally unstable azo compounds.

  DOI：

  10.1021/jo00092a013
• 作为产物：
  描述：

  4-thia-2,6-diazatricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 36.0h， 以74.1%的产率得到4-Thia-2,6-diazatricyclo<5.2.2.0>undecane-3,5-dione
  参考文献：
  名称：

  1-Thia-3,4-diazolidine-2,5-dione functionality: a photochemical synthon for the azo group

  摘要：

  The 1-thia-3,4-diazolidine-2,5-dione functional group was shown to yield azo compounds upon photolysis. This photoreaction when combined with the known ability of this group to react in a Diels-Alder fashion or as a dinucelophile toward alkylating agents greatly increases the utility of this functionality. The dual reactivity of this group was demonstrated in the synthesis of a number of 3,4-dialkyl-1-thia-3,4-diazolidine-2,5-diones. The photolysis of these compounds produced either thermally stable cyclic azo compounds or the decomposition products of thermally unstable azo compounds.

  DOI：

  10.1021/jo00092a013

文献信息

• Syntheses and reactions of 3,4-dialkyl-1,3,4-thiadiazolidine-2,5-diones
  作者：Steven W. Moje、Peter Beak

  DOI：10.1021/jo00934a003

  日期：1974.10
• A Photoactivable Fluorophore Based on Thiadiazolidinedione as Caging Group
  作者：Gabriela Gramlich、Werner M. Nau

  DOI：10.1021/ol9906965

  日期：1999.8.1

  [GRAPHICS]Photoactivable ("caged") fluorescent dyes and probes are crucial for temporally and spatially resolved tracer experiments, e.g., in cell biology or fluid physics. The thiadiazolidinedione 1 represents a new class of caged fluorophore. Upon UV-irradiation it releases in a rapid photoreaction with high quantum yield the azoalkane 2. Longer wavelength excitation of 2 to the singlet excited state results in strong and long-lived fluorescence with maximum intensity at 425 nm. It has been demonstrated that one single uncaging laser pulse suffices for time-resolved or steady-state detection of the fluorescence.
• The Preparation of 1,3,4-Thiadiazoline-2,5-dione and Its Use as a Dienophilic Reagent
  作者：E. Corey、Barry Snider

  DOI：10.1021/jo00960a600

  日期：1973.10
• Squiliacote Michael, De Felippis James, J. Org. Chem, 59 (1994) N 13, S 3564-3571
  作者：Squiliacote Michael, De Felippis James

  DOI：——

  日期：——
• MOJE S. W.; BEAK P., J. ORG. CHEM. <JOCE-AH>, 1974, 39, NO 20, 2951-2956
  作者：MOJE S. W.、 BEAK P.

  DOI：——

  日期：——