5-dimethylsulfonio-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide | 5362-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-dimethylsulfonio-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide
• 英文别名: 5-Dimethylsulfonium-2.2-dimethyl-<4.6-dioxo-1.3-dioxan>-ylid；5-Dimethylsulfonium-2,2-dimethyl-(4,6-dioxo-1,3-dioxan)-ylid；Dimethylsulfonium-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylid；5-Dimethylsulfonio-4,6-dioxo-2,2-dimethyl-1,3-dioxan；Dimethylsulfonium-meldrumsaeure-ylid；5-(Dimethyl-lambda4-sulfanylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione；5-(dimethyl-λ4-sulfanylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 5362-80-1
• 化学式: C₈H₁₂O₄S
• 分子量: 204.247
• InChiKey: UGYZYBKWMRFPRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-dimethylsulfonio-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 5-Hydroxy-5-(1-hydroxy-4,4-dimethyl-2,6-dioxocyclohexyl)-2,2-dimethyl-1,3-dioxan-4,6-dion
  参考文献：
  名称：

  Schank, Kurt; Schuhknecht, Christoph, Chemische Berichte, 1982, vol. 115, # 9, p. 3032 - 3041

  摘要：

  DOI：
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 在 sodium hydroxide 、 溴 作用下， 以 水 为溶剂， 反应 24.67h， 生成 5-dimethylsulfonio-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide
  参考文献：
  名称：

  Chemistry of diazocarbonyl compounds: XXV. Comparative photochemistry of diazo compounds and sulfur ylides of the 1,3-dioxane-4,6-dione series

  摘要：

  Photochemical decomposition of 2,2-dialkyl-5-diazo-1,3-dioxane-4,6-diones in the presence of pyridine, methanol.. or dimethyl sulfide as carbene traps involves mainly the Wolff rearrangement which is likely to follow a concerted pattern, while the yield of the "carbene" products does not exceed 27-28%. No carbene intermediates are formed in the photolysis of the corresponding dioxo sulfonium ylides under analogous conditions, and the main photochemical process is 1,2-methyl shift (Stevens rearrangement), followed by photochemical transformations of the primary products according to the Norrish type 11 pattern.

  DOI：

  10.1134/s1070428006060029

文献信息

• Search for dioxocarbenes in photochemical reactions of 5-diazo-4,6-dioxo-1,3-dioxanes, associated diazirines, and S-ylides
  作者：V.V. Shevchenko、N.N. Khimich、M.S. Platz、V.A. Nikolaev

  DOI：10.1016/j.tetlet.2004.11.102

  日期：2005.1

  On direct photolysis of 2,2-dialkyl-5-diazo-4,6-dioxo-1,3-dioxanes in the presence of pyridine, methanol or dimethyl sulfide as carbene traps, the yield of ‘carbene’ products does not exceed 27–28%. At the same time photochemical transformations of the related 3,3-diacyldiazirines and dioxosulfonium ylides of this series, evidently, occur without generation of carbene intermediates.

  在存在吡啶，甲醇或二甲基硫醚作为卡宾捕集剂的情况下，对2,2-二烷基-5-重氮-4,6-二氧代-1,3-二恶烷进行直接光解时，“卡宾”产物的收率不超过27 –28％。同时，与此相关的3，3-二酰基二叠氮基和该系列二氧代ulf鎓的光化学转化显然发生了，而没有产生卡宾中间体。
• SCHANK K.; SCHUHKNECHT C., SYNTHESIS, 1978, NO 9, 678
  作者：SCHANK K.、 SCHUHKNECHT C.

  DOI：——

  日期：——
• NIKOLAEV V. A.; FRENX YU.; KOROBITSINA I. K., ZH. ORGAN. XIMII, 1978, 14, HO 7, 1433-1441
  作者：NIKOLAEV V. A.、 FRENX YU.、 KOROBITSINA I. K.

  DOI：——

  日期：——
• Chemistry of diazocarbonyl compounds: XXV. Comparative photochemistry of diazo compounds and sulfur ylides of the 1,3-dioxane-4,6-dione series
  作者：V. A. Nikolaev、V. V. Shevchenko、M. S. Platz、N. N. Khimich

  DOI：10.1134/s1070428006060029

  日期：2006.6

  Photochemical decomposition of 2,2-dialkyl-5-diazo-1,3-dioxane-4,6-diones in the presence of pyridine, methanol.. or dimethyl sulfide as carbene traps involves mainly the Wolff rearrangement which is likely to follow a concerted pattern, while the yield of the "carbene" products does not exceed 27-28%. No carbene intermediates are formed in the photolysis of the corresponding dioxo sulfonium ylides under analogous conditions, and the main photochemical process is 1,2-methyl shift (Stevens rearrangement), followed by photochemical transformations of the primary products according to the Norrish type 11 pattern.
• Schank, Kurt; Schuhknecht, Christoph, Chemische Berichte, 1982, vol. 115, # 9, p. 3032 - 3041
  作者：Schank, Kurt、Schuhknecht, Christoph

  DOI：——

  日期：——