endo-<1R,4S,4aS,9aR,(S)S>-1,4-Ethano-8-methoxy-4a-(p-tolylsulfinyl)-1,4,4a,9a-tetrahydro-9,10-anthraquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: endo-<1R,4S,4aS,9aR,(S)S>-1,4-Ethano-8-methoxy-4a-(p-tolylsulfinyl)-1,4,4a,9a-tetrahydro-9,10-anthraquinone
• 英文别名: endo-(1R,4S,4aS,9aR,(S)S)-1,4-Ethano-8-methoxy-4a-(p-tolylsulfinyl)-1,4,4a,9a-tetrahydro-9,10-anthraquinone；(1S,2S,11R,12R)-8-methoxy-2-[(S)-(4-methylphenyl)sulfinyl]tetracyclo[10.2.2.02,11.04,9]hexadeca-4(9),5,7,13-tetraene-3,10-dione
• 化学式: C₂₄H₂₂O₄S
• 分子量: 406.502
• InChiKey: DPFIWWDMKGPALE-VOLPXGRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  endo-<1R,4S,4aS,9aR,(S)S>-1,4-Ethano-8-methoxy-4a-(p-tolylsulfinyl)-1,4,4a,9a-tetrahydro-9,10-anthraquinone 以 二氯甲烷 为溶剂， 反应 24.0h， 以84%的产率得到(+)-(1S,4R)-1,4-Ethano-5-methoxy-1,4-dihydro-9,10-anthraquinone
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones

  摘要：

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.

  DOI：

  10.1021/jo00051a036
• 作为产物：
  描述：

  (S)-5-methoxy-2-(p-tolylsulfinyl)-1,4-naphthoquinone 、 1,3-环己二烯 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以82%的产率得到endo-<1R,4S,4aS,9aR,(S)S>-1,4-Ethano-8-methoxy-4a-(p-tolylsulfinyl)-1,4,4a,9a-tetrahydro-9,10-anthraquinone
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones

  摘要：

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.

  DOI：

  10.1021/jo00051a036

文献信息

• Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones
  作者：M. Carmen Carreno、Jose L. Garcia Ruano、Antonio Urbano

  DOI：10.1021/jo00051a036

  日期：1992.12

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.