2-(4-Methylphenyl)sulfinylfuran | 159169-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-Methylphenyl)sulfinylfuran
• CAS: 159169-40-1
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: HFWHJXNVIDLPAS-UHFFFAOYSA-N

物化性质

• 沸点：
  346.9±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-二溴-3-戊酮 、 2-(4-Methylphenyl)sulfinylfuran 在 铜 、 sodium iodide 作用下， 以 乙腈 为溶剂， 生成 (1R,2R,4R,5R)-2,4-Dimethyl-1-(toluene-4-sulfinyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 、 (1R,2S,4S,5R)-2,4-Dimethyl-1-(toluene-4-sulfinyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one
  参考文献：
  名称：

  alpha-Hetero-substituted Furans as Dienes in [4+3] Cycloadditions with 1,3-Dimethyloxyallyl Cation for the Preparation of New Versatile Cycloheptane Synthons: A Study of the Factors Controlling the Diastereoselectivity.

  摘要：

  [4+3] Cycloaddition reactions of 2-functionalized furans with 1,3-dimethyloxyallyl cation, afford versatile polyfunctionalized cycloheptane synthons. Increasing electron-donating properties and/or decreasing size of the substituent at C-2 of furan improves yield but decreases stereoselectivity. The opposite effect is also observed, so, by designing a bulky enough alpha-substituent it is possible to obtain endo stereospecificity. cis Stereospecificity is observed in all studied cases and it is probably determined by the type of reaction mechanism.

  DOI：

  10.3891/acta.chem.scand.52-0453
• 作为产物：
  描述：

  (-)-menthyl p-toluenesulfinate 在 正丁基锂 、 magnesium bromide 、 lithium diisopropyl amide 作用下， 生成 2-(4-Methylphenyl)sulfinylfuran
  参考文献：
  名称：

  制备旋光的2-（或3）（对甲苯基亚磺酰基）-3（或2）呋喃基或噻吩基甲醛

  摘要：

  通过（1）-（-）-Ss-薄荷基-对甲苯亚磺酸盐在呋喃或噻吩前体上的反应描述了四种对映体纯的标题化合物的制备。

  DOI：

  10.1016/0957-4166(95)00266-r

文献信息

• alpha-Hetero-substituted Furans as Dienes in [4+3] Cycloadditions with 1,3-Dimethyloxyallyl Cation for the Preparation of New Versatile Cycloheptane Synthons: A Study of the Factors Controlling the Diastereoselectivity.
  作者：Angel M. Montaña、Sandra Ribes、Pedro M. Grima、Francisca Garcia、Louisa Barré、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0453

  日期：——

  [4+3] Cycloaddition reactions of 2-functionalized furans with 1,3-dimethyloxyallyl cation, afford versatile polyfunctionalized cycloheptane synthons. Increasing electron-donating properties and/or decreasing size of the substituent at C-2 of furan improves yield but decreases stereoselectivity. The opposite effect is also observed, so, by designing a bulky enough alpha-substituent it is possible to obtain endo stereospecificity. cis Stereospecificity is observed in all studied cases and it is probably determined by the type of reaction mechanism.
• Preparation of optically active 2-(or 3)(p-tolylsulfinyl)-3(or 2)furyl- or thienylcarboxaldehydes
  作者：Laurent D. Girodier、Christian S. Maignan、Francis P. Rouessac

  DOI：10.1016/0957-4166(95)00266-r

  日期：1995.8

  The preparation of the four enantiomerically pure title compounds is described by reaction of (1)-(−)-Ss-menthyl-p-toluenesulfinate on furan or thiophene precursors.

  通过（1）-（-）-Ss-薄荷基-对甲苯亚磺酸盐在呋喃或噻吩前体上的反应描述了四种对映体纯的标题化合物的制备。

表征谱图