(1R,2R,4R)-(+)-oxabicyclo<2.2.1>hept-5-ene-2-p-tolyl sulfide | 134297-24-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1R,2R,4R)-(+)-oxabicyclo<2.2.1>hept-5-ene-2-p-tolyl sulfide
• CAS: 134297-24-8
• 化学式: C₁₃H₁₄OS
• 分子量: 218.32
• InChiKey: HHOLISCENLRXGP-CYZMBNFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R)-(+)-oxabicyclo<2.2.1>hept-5-ene-2-p-tolyl sulfide 在 N-氯代丁二酰亚胺 、 copper(II) oxide 、 copper dichloride 作用下， 生成 (1R,4R)-(+)-7-oxabicyclo<2.2.1>hept-5-en-2-one
  参考文献：
  名称：

  Highly diastereoselective Diels-Alder reactions with (R)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate

  摘要：

  p-Tolyl vinyl sulfoxide has been efficiently activated for Diels-Alder reactions by transformation into a sulfonium salt 3a or by addition of TMSOTf. Very high diastereomeric excesses have been achieved (> 98%) at -20-degrees-C in many cases. Best results have been obtained with cyclopentadiene, furan and 2,3-dimethyl-1,3-butadiene. In this way enantiomerically pure oxanorbornenone 19a has been prepared. The reaction mechanism is briefly discussed.

  DOI：

  10.1016/s0957-4166(00)82159-x
• 作为产物：
  描述：

  (S)-(-)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate 在 吡啶 、 sodium hydroxide 、 a-丙烯酸氯甲酯 作用下， 反应 67.5h， 生成 (1R,2R,4R)-(+)-oxabicyclo<2.2.1>hept-5-ene-2-p-tolyl sulfide
  参考文献：
  名称：

  Highly diastereoselective Diels-Alder reactions with (R)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate

  摘要：

  p-Tolyl vinyl sulfoxide has been efficiently activated for Diels-Alder reactions by transformation into a sulfonium salt 3a or by addition of TMSOTf. Very high diastereomeric excesses have been achieved (> 98%) at -20-degrees-C in many cases. Best results have been obtained with cyclopentadiene, furan and 2,3-dimethyl-1,3-butadiene. In this way enantiomerically pure oxanorbornenone 19a has been prepared. The reaction mechanism is briefly discussed.

  DOI：

  10.1016/s0957-4166(00)82159-x