2-acetyl-4,5-dimethyl-3,6-dihydro-2H-thiopyran | 80738-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 2-acetyl-4,5-dimethyl-3,6-dihydro-2H-thiopyran
• 英文别名: 1-(4,5-dimethyl-3,6-dihydro-2H-thiopyran-2-yl)ethanone
• CAS: 80738-11-0
• 化学式: C₉H₁₄OS
• 分子量: 170.276
• InChiKey: IHHMRDVJPRTCIF-UHFFFAOYSA-N

物化性质

• 沸点：
  260.3±40.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 丙酮醛 在 双(三甲基硫化硅) 、 cobalt(II) chloride 作用下， 以 乙腈 为溶剂， 以70%的产率得到2-acetyl-4,5-dimethyl-3,6-dihydro-2H-thiopyran
  参考文献：
  名称：

  Silicon-assisted synthesis of thiocarbonyl derivatives and reactivity of dienophilic thioaldehydes

  摘要：

  Treatment of bis(trimethylsilyl) sulfide with CoCl2.6H2O in the presence of aldehydes affords the corresponding thiocarbonyl analogues which can be trapped to avoid polymerization. The sulfurization reaction also takes place in the presence of TfOSiMe3, in which case, besides thioaldehydes, thioketones may be obtained in satisfactory yields. When thioaldehydes are generated with the CoCl2.6H2O method the Diels-Alder reaction with cyclohexadiene occurs with very high selectivity in favor of the endo isomer, whereas when the TfOSiMe3-based method is employed, the stereochemistry of the cycloadduct can be conveniently selected toward endo or exo by varying the molar ratio of the sulfurating agent.

  DOI：

  10.1021/jo00026a025

文献信息

• A Novel Formation of Thiocarbonyl Compounds from Phosphorus Ylides with Cyclic Polysulfide as the Sulfuration Reagent
  作者：Ryu Sato、Shin-ichi Satoh

  DOI：10.1055/s-1991-26574

  日期：——

  The reaction of cyclic polysulfides, such as 5H-1,2,3,4-benzotetrathiepin and 6H-1,2,3,4,5-benzopentathiocin as the sulfuration reagent with relatively stable phosphorus ylides affords efficiently thiocarbonyl compounds such as thioaldehydes and thioketones, which further react with 2,3-dimethyl-1,3-butadiene or cyclopentadiene in situ to give various 5,6-dihydro-2H-thiopyrans and 2-thiabicyclo[2.2.1]hept-5-enes in satisfactory yields.

  将环状多硫化物（如 5H-1,2,3,4-苯并四硫杂卓和 6H-1,2,3,4,5-苯并五硫杂卓作为硫化试剂）与相对稳定的酰化磷反应，可高效生成硫代羰基化合物（如硫代醛和硫酮）、 这些化合物与 2,3-二甲基-1,3-丁二烯或环戊二烯发生原位反应，生成各种 5,6-二氢-2H-硫代吡喃和 2-硫杂双环[2.2.1]庚-5-烯，产量令人满意。
• Thioaldehyde Diels-Alder reactions
  作者：E. Vedejs、T. H. Eberlein、D. J. Mazur、C. K. McClure、D. A. Perry、R. Ruggeri、E. Schwartz、J. S. Stults、D. L. Varie

  DOI：10.1021/jo00359a034

  日期：1986.5
• Dienophilic thioaldehydes
  作者：E. Vedejs、T. H. Eberlein、D. L. Varie

  DOI：10.1021/ja00369a059

  日期：1982.3
• Formation of Thioaldehyde Intermediates by Thermolysis of Sulfoxides Bearing Some Heteroaromatics
  作者：Hiroyuki Morita、Masahiro Takeda、Takayoshi Fujii、Toshiaki Yoshimura、Choichiro Shimasaki

  DOI：10.1021/jo9700181

  日期：1997.12.1

  Thermal reactions of phenacyl sulfoxide bearing heterocycles, such as a 2-benzothiazolyl or N-oxypyridyl group, in the presence of 2,3-dimethyl-1,3-butadiene afforded 6-benzoyl-5,6-dihydro-3,4-dimethyl-2H-thiapyran in good yield. This product is considered to be formed by the Diels-Alder reaction of a diene with thioaldehyde formed initially by the decomposition of sulfoxides.
• DEGLNNOCENTI, ALESSANDRO;RICCI, ALFREDO;CAPPERUCCI, ANTONELLA;MORDINI, AL+, PHOSPH., SULFUR AND SILICON AND RELAT. ELEM., 58-59,(1991) N-4, C. 117-12+
  作者：DEGLNNOCENTI, ALESSANDRO、RICCI, ALFREDO、CAPPERUCCI, ANTONELLA、MORDINI, AL+

  DOI：——

  日期：——