(1S,2S,4S)-2-(4-chlorophenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene | 1262638-61-8

• 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: (1S,2S,4S)-2-(4-chlorophenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene
• 英文别名: (1S,4S,5S)-5-(4-chlorophenyl)sulfonyl-7-oxabicyclo[2.2.1]hept-2-ene
• CAS: 1262638-61-8
• 化学式: C₁₂H₁₁ClO₃S
• 分子量: 270.737
• InChiKey: QCSGVANOBJZUOW-USWWRNFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-chlorophenylsulfinyl)-7-oxabicyclo[2.2.1]hept-5-ene 在 potassium peroxomonosulfate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 (1S,2R,4S)-2-(4-chlorophenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene 、 (1R,2R,4R)-2-(4-chlorophenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene 、 (1S,2S,4S)-2-(4-chlorophenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  Enantioselective Synthesis of 2,2,5-Tri- and 2,2,5,5-Tetrasubstituted Tetrahydrofuransvia[4 + 2] Cycloaddition and Ring-Opening Cross-Metathesis

  摘要：

  A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Diels-Alder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed Into 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans, which are structural subunits of many natural products, via regioselective ring-opening metathesis/cross-metathesis or oxidative cleavage/refunctionalization.

  DOI：

  10.1021/ol102798f