(S)-5-methoxy-2-(p-tolylsulfinyl)-1,4-naphthoquinone | 134281-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-5-methoxy-2-(p-tolylsulfinyl)-1,4-naphthoquinone
• 英文别名: (S)-5-methoxy-2-p-tolylsulfinyl-1,4-naphthoquinone；5-methoxy-2-[(S)-(4-methylphenyl)sulfinyl]naphthalene-1,4-dione
• CAS: 134281-85-9
• 化学式: C₁₈H₁₄O₄S
• 分子量: 326.373
• InChiKey: LPDCWCCWOKPHQQ-QHCPKHFHSA-N

物化性质

• 沸点：
  584.8±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  (S)-5-methoxy-2-(p-tolylsulfinyl)-1,4-naphthoquinone 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (+)-(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)-1,4,5-trimethoxy-2-p-tolylsulfinylnaphthalene 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以82%的产率得到(S)-5-methoxy-2-(p-tolylsulfinyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of Optically Activep-Tolylsulfinylquinones

  摘要：

  标题化合物3a-e是通过对1a-e的1,4-二甲氧基芳烃前体进行硫烯化，再用硝酸铵铈(IV)氧化，仅需两个步骤制备而成。

  DOI：

  10.1055/s-1992-26189

文献信息

• General synthesis of chiral 2-p-tolylsulfinylquinones.
  作者：M.Carmen Carreño、Jośe L. García Ruano、Jośe M. Mata、Antonio Urbano

  DOI：10.1016/s0040-4020(01)87050-2

  日期：1991.1

  Optically pure (S)-p-tolylsulfinyl substituted quinones were synthesized by deketalization of the corresponding quinone bisketals obtained by Andersen's type synthesis starting from 2-bromo-1,4-dimethoxy aromatic derivatives, followed by anodic oxidation of the resulting sulfoxide.
• Influence of the Sulfinyl Group on the Chemoselectivity and π-Facial Selectivity of Diels−Alder Reactions of <i>(S)</i>-2-(<i>p</i>-Tolylsulfinyl)-1,4-benzoquinone
  作者：M. Carmen Carreño、José L. García Ruano、Miguel A. Toledo、Antonio Urbano、Cynthia Z. Remor、Valter Stefani、Jean Fischer

  DOI：10.1021/jo951438y

  日期：1996.1.1

  Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyclohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C-2-C-3 versus C-5-C-6 double bonds) is mainly related to the cyclic (on C-5-C-6) or acyclic (on C-2-C-3) structure of the diene. The high pi-facial selectivity observed could be controlled by choosing adequate experimental conditions.
• Synthesis of Optically Active<i>p</i>-Tolylsulfinylquinones
  作者：M. Carmen Carreño、José L. García Ruano、Antonio Urbano

  DOI：10.1055/s-1992-26189

  日期：——

  The title compounds 3a-e were prepared in only two steps from 1,4-dimethoxyaromatic precursors 1a-e by sulfinylation followed by oxidation with ammonium cerium(IV) nitrate.

  标题化合物3a-e是通过对1a-e的1,4-二甲氧基芳烃前体进行硫烯化，再用硝酸铵铈(IV)氧化，仅需两个步骤制备而成。
• 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.