8,8-dimethyl-5,5-dioxo-1-aza-2-oxa-5-thiabicyclo<3.2.1>octane | 122603-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 8,8-dimethyl-5,5-dioxo-1-aza-2-oxa-5-thiabicyclo<3.2.1>octane
• 英文别名: 8,8-dimethyl-5,5-dioxo-1-aza-2-oxa-5-thiabicyclo[3.2.1]octane；8,8-Dimethyl-7-oxa-4lambda6-thia-1-azabicyclo[3.2.1]octane 4,4-dioxide；8,8-dimethyl-7-oxa-4λ6-thia-1-azabicyclo[3.2.1]octane 4,4-dioxide
• CAS: 122603-52-5
• 化学式: C₇H₁₃NO₃S
• 分子量: 191.251
• InChiKey: RSESMDLDCOSXKT-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  333.6±52.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙酮肟 、 二乙烯基砜 生成 8,8-dimethyl-5,5-dioxo-1-aza-2-oxa-5-thiabicyclo<3.2.1>octane
  参考文献：
  名称：

  PADWA, ALBERT;NORMAN, BRYAN H., TETRAHEDRON LETT., 29,(1988) N 20, 2417-2420

  摘要：

  DOI：

文献信息

• X=Y-ZH systems as potential 1,3-dipoles. Part 34. generation of nitrones from oximes. Tandem michael addition-1,3-dipolar cycloaddition reactions. class 2 processes utilising bifunctional michael acceptor-dipolarophile components.
  作者：Ronald Grigg、Michael J. Dorrity、Frances Heaney、John F. Malone、Shuleewan Rajviroongit、Visuvanathar Sridharan、Sivagnanasundram Surendrakumar

  DOI：10.1016/s0040-4020(01)91022-1

  日期：1991.9

  Aldoximes and ketoximes react with a range of bifunctional Michael acceptor-dipolarophile substrates comprising functionalised 1,3-, 1,4- and 1,5-dienes via a tandem process involving an N-alkenyl nitrone intermediate. The 1,3-dienes react regio- and stereo-specifically to give 1-aza-7-oxabicyclo[2.2.1]heptanes whilst sterically unencumbered aryl aldoximes and 1,4-dienes give 1-aza-2-oxabicyclo[3.2

  醛酮肟和酮肟通过涉及N-烯基硝酮中间体的串联过程与一系列包含官能化的1,3-，1,4-和1,5-二烯的双官能Michael受体-双极性亲和底物反应。1,3-二烯在区域和立体上发生特异性反应，生成1-氮杂-7-氧杂双环[2.2.1]庚烷，而空间上不受阻碍的芳基醛肟和1,4-二烯生成1-氮杂-2-氧杂双环[3.2]。 1]辛烷衍生物。1-Aza-2-oxa-和1-aza-8-oxa-双环[3.2.1]辛烷的酮肟和1.4消旋混合物。1,5-二烯和酮肟与区域和立体特异性反应，生成1-aza-8-氧杂双环[3.2.1]辛烷衍生物，而苯甲醛肟则生成1：1异构体的1-aza-8-氧杂双环[3.2]混合物。 1]辛烷以及两个差向异构的1-氮杂-2-氧杂双环[3.2.1]辛烷。串联过程的区域和立体化学结果受双功能底物中连接链的长度和性质以及在过渡状态下肟和双极性亲核体上取代基之间的空间相互作用所控制。据报道1-氮杂-7-氧杂双环[2
• 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.
• NORMAN, BRYAN H.;GAREAU, YVES;PADWA, ALBERT, J. ORG. CHEM., 56,(1991) N, C. 2154-2161
  作者：NORMAN, BRYAN H.、GAREAU, YVES、PADWA, ALBERT

  DOI：——

  日期：——
• PADWA, ALBERT;NORMAN, BRYAN H., TETRAHEDRON LETT., 29,(1988) N 20, 2417-2420
  作者：PADWA, ALBERT、NORMAN, BRYAN H.

  DOI：——

  日期：——