(+)-<3aS,4S,7R,7aS,(S)R>-2-Methyl-4-phenyl-7-(p-tolylsulfinyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione | 155409-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (+)-<3aS,4S,7R,7aS,(S)R>-2-Methyl-4-phenyl-7-(p-tolylsulfinyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione
• 英文别名: (3aR,4R,7S,7aS)-2-methyl-4-[(R)-(4-methylphenyl)sulfinyl]-7-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione
• CAS: 155409-83-9
• 化学式: C₂₂H₂₁NO₃S
• 分子量: 379.48
• InChiKey: ZKXYTQWFIVCDMX-WSUZPRCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 (+)-<3aS,4S,7R,7aS,(S)R>-2-Methyl-4-phenyl-7-(p-tolylsulfinyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione 以 二氯甲烷 为溶剂， 反应 48.0h， 以68%的产率得到(+)-(3aR,7aR)-2-Methyl-4-phenyl-3a,7a-dihydroisoindole-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：

  N-甲基马来酰亚胺 、 (1E,3E)-(+)-(R)-1-(p-tolylsulfinyl)-4-phenyl-1,3-butadiene 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 432.0h， 以65%的产率得到(+)-<3aS,4S,7R,7aS,(S)R>-2-Methyl-4-phenyl-7-(p-tolylsulfinyl)-3a,4,7,7a-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

文献信息

• First Diels-Alder Reactions of Enantiomerically Pure 1-p-Tolylsulfinyl Dienes: Straightforward Access to Cyclohexenols through Tandem Cycloaddition/[2,3]-Sigmatropic Rearrangement
  作者：Eva Arce、M. Carmen Carreno、M. Belen Cid、Jose L. Garcia Ruano

  DOI：10.1021/jo00091a035

  日期：1994.6

  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.