(+)-<(S)R>-1-Ethoxy-2-methyl-4-(p-tolylsulfinyl)-1,3-butadiene | 155409-79-3

• 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: (+)-<(S)R>-1-Ethoxy-2-methyl-4-(p-tolylsulfinyl)-1,3-butadiene
• 英文别名: 1-[(R)-[(1E,3E)-4-ethoxy-3-methylbuta-1,3-dienyl]sulfinyl]-4-methylbenzene
• CAS: 155409-79-3
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: IZURJMIHZFOXNX-UMQDQBQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 (+)-<(S)R>-1-Ethoxy-2-methyl-4-(p-tolylsulfinyl)-1,3-butadiene 以 二氯甲烷 为溶剂， 反应 648.0h， 以71%的产率得到(-)-(3aR,4R,5S,7aR)-4-Ethoxy-5-hydroxy-2,5-dimethyl-3a,4,5,7a-tetrahydroisoindole-1,3-dione
  参考文献：
  名称：

  First Diels-Alder Reactions of Enantiomerically Pure 1-p-Tolylsulfinyl Dienes: Straightforward Access to Cyclohexenols through Tandem Cycloaddition/[2,3]-Sigmatropic Rearrangement

  摘要：

  The asymmetric Diels-Alder reactions of (R)-1-(p-tolylsulfinyl)-1,3-butadienes 3a-c with N-methylmaleimide (NMM) have been explored. The cycloadditions are stereospecific: only one endo adduct is formed, the pi-facial diastereoselectivity being controlled by the sulfoxide both in thermal and catalytic conditions. The in situ cycloaddition/sulfoxide sulfenate [2,3]-sigmatropic rearrange ment starting from chiral 3a-e in the presence of an excess of NMM, which acts as thiophilic agent, provides a convenient one-step access to enantiomerically pure and all-cis functionalized cyclohexenols (-)-5a-c.

  DOI：

  10.1021/jo00091a035
• 作为产物：
  描述：

  (R)-(+)-甲基对甲苯砜 在 sodium hydride 、 lithium diisopropyl amide 、 碘甲烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 22.83h， 生成 (+)-<(S)R>-1-Ethoxy-2-methyl-4-(p-tolylsulfinyl)-1,3-butadiene
  参考文献：
  名称：

  First Diels-Alder Reactions of Enantiomerically Pure 1-p-Tolylsulfinyl Dienes: Straightforward Access to Cyclohexenols through Tandem Cycloaddition/[2,3]-Sigmatropic Rearrangement

  摘要：

  The asymmetric Diels-Alder reactions of (R)-1-(p-tolylsulfinyl)-1,3-butadienes 3a-c with N-methylmaleimide (NMM) have been explored. The cycloadditions are stereospecific: only one endo adduct is formed, the pi-facial diastereoselectivity being controlled by the sulfoxide both in thermal and catalytic conditions. The in situ cycloaddition/sulfoxide sulfenate [2,3]-sigmatropic rearrange ment starting from chiral 3a-e in the presence of an excess of NMM, which acts as thiophilic agent, provides a convenient one-step access to enantiomerically pure and all-cis functionalized cyclohexenols (-)-5a-c.

  DOI：

  10.1021/jo00091a035