2-methylenetetrahydropyran 1,1-dioxide | 79496-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 2-methylenetetrahydropyran 1,1-dioxide
• 英文别名: 2-methylenethian 1,1-dioxide；2-Methylidenethiane 1,1-dioxide
• CAS: 79496-72-3
• 化学式: C₆H₁₀O₂S
• 分子量: 146.21
• InChiKey: XWPLWYJKSZHAMN-UHFFFAOYSA-N

物化性质

• 沸点：
  309.1±12.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲磺酸己-5-炔基酯 在 过氧十二烷酸 、 sodium isopropylate 作用下， 以 乙醚 、 异丙醇 、 xylene 、 Petroleum ether 为溶剂， 反应 18.92h， 生成 2-methylenetetrahydropyran 1,1-dioxide
  参考文献：
  名称：

  通过亚硫酸分子内和分子间加成到炔烃中合成烯基亚砜

  摘要：

  通过在140℃下热解ω-（叔丁基亚磺酰基）炔烃形成的炔基-ω-亚磺酸，在区域特异性地环化成2-亚甲基硫代环烷烃1-氧化物；以此方式未形成2-亚甲基噻吨-1-氧化物。通过加热二叔丁基亚砜而获得的2-甲基丙烷-2-磺酸，被区域选择性地加入到辛基-1-炔中，主要生成2-叔丁基亚磺酰基辛基-1-烯，后者本身会热分解为二辛烯基亚砜的混合物。通过链烷磺酸-二烷基硫的相互转化。通过1-氰基-2-烷基（或芳基）亚磺酰基乙烷的热分解可方便地生成苯甲磺酸，甲磺酸和乙氧基羰基甲磺酸，将它们在分子间加成至选择性地生成未活化和活化的炔烃中，从而以良好的产率得到链烯基亚砜。

  DOI：

  10.1039/p19810002106

文献信息

• Mild convenient synthesis of α-methylene sulfones
  作者：James B. Hendrickson、Paul S. Palumbo

  DOI：10.1016/s0040-4039(00)98853-1

  日期：1985.1

  Reaction of paraformaldehyde with α-trifyl-sulfones and potassium carbonate at room temperature affords vinyl sulfones in good yield under mild conditions, with loss of triflate anion.

  在室温下将多聚甲醛与α-三氟甲基砜和碳酸钾反应，可在温和的条件下以良好的收率得到乙烯基砜，且三氟甲磺酸根阴离子损失掉。
• Regiochemical and stereochemical studies on halocyclization reactions of unsaturated sulfides
  作者：Xiao-Feng Ren、Edward Turos、Charles H. Lake、Melvyn Rowen Churchill

  DOI：10.1021/jo00125a038

  日期：1995.10

  The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent. Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts. The endo- versus exo-regioselectivity of these alkenyl sulfide ring closures most likely reflects the difference in thermodynamic stabilities of the beta-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate. The efficiency of the cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers. Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides. Conversely the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length. Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring, The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control. The methodology has been applied to the synthesis of unusual bicyclic beta-lactams related to the penicillin family of antibiotics.
• BELL, B. R.;COTTAM, P. D.;DAVIES, J.;JONES, D. N., J. CHEM. SOC. PERKIN TRANS., 1981, N 7, 2106-2115
  作者：BELL, B. R.、COTTAM, P. D.、DAVIES, J.、JONES, D. N.

  DOI：——

  日期：——
• HENDRICKSON, J. B.;PALUMBO, P. S., TETRAHEDRON LETT., 1985, 26, N 24, 2849-2852
  作者：HENDRICKSON, J. B.、PALUMBO, P. S.

  DOI：——

  日期：——
• PROTEASOME ACTIVITY ENHANCING COMPOUNDS
  申请人：Proteostasis Therapeutics, Inc.

  公开号：EP3814338A1

  公开（公告）日：2021-05-05