(S)-2-p-tolylsulfinyl-1,4-naphthoquinone | 134281-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-p-tolylsulfinyl-1,4-naphthoquinone
• 英文别名: (+)-(SS)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone；2-[(S)-(4-methylphenyl)sulfinyl]naphthalene-1,4-dione
• CAS: 134281-84-8
• 化学式: C₁₇H₁₂O₃S
• 分子量: 296.346
• InChiKey: MFOWNRQSLHZDLR-NRFANRHFSA-N

物化性质

• 沸点：
  528.2±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-p-tolylsulfinyl-1,4-naphthoquinone 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 1,4-Methano-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)-1,1,4,4-tetramethoxy-2-p-tolylsulfinyl-1,4-dihydronaphthalene 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以75%的产率得到(S)-2-p-tolylsulfinyl-1,4-naphthoquinone
  参考文献：
  名称：

  General synthesis of chiral 2-p-tolylsulfinylquinones.

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)87050-2

文献信息

• 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。
• Studies of Diastereoselectivity in Diels−Alder Reactions of Enantiopure (S<i>S</i>)-2-(<i>p</i>-Tolylsulfinyl)-1,4-naphthoquinone and Chiral Racemic Acyclic Dienes
  作者：M. Carmen Carreño、Susana García-Cerrada、Antonio Urbano、Claudio Di Vitta

  DOI：10.1021/jo000210u

  日期：2000.7.1

  Enantiopure sulfinylnaphthoquinone (+)-5 reacted with racemic acyclic dienes 1a-f bearing a stereogenic allylic center, through a tandem cycloaddition/pyrolytic sulfoxide elimination, to afford optically enriched compounds 8a-f and 9a-f with good like/unlike selectivities (ca. 75:25) and good enantiomeric excesses (68-82%), arising from the partial kinetic resolution of the racemic dienes. The opposite

  对映纯亚磺酰基萘醌（+）-5通过串联环加成/热解亚砜与带有立体异构烯丙基中心的消旋无环二烯1a-f反应，得到光学富集的化合物8a-f和9a-f，具有良好的相似/不相似的选择性（ca 75:25）和良好的对映体过量（68-82％），这是由外消旋二烯的部分动力学拆分引起的。在与二烯1g-i的反应中观察到相反的非对映异构（8g-i：9g-i，至5:95），二烯在C-3处具有额外的甲基，对映体纯度为中等（14-25％）。相应方法中的立体效应和扭转相互作用说明了观察到的非对映选择性。
• Enantioselective Diels-Alder Approach to C-3-Oxygenated Angucyclinones from (SS)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone
  作者：M. Carmen Carreño、Antonio Urbano、Claudio Di Vitta

  DOI：10.1002/(sici)1521-3765(20000303)6:5<906::aid-chem906>3.0.co;2-g

  日期：2000.3.3

  quinones anti-6 and syn-7, which were obtained from the kinetic resolution of the racemic diene. In all cases, (SS)-(2-p-tolylsulfinyl)-1,4-naphthoquinone reacted from the less hindered face of the more reactive s-cis conformation, to form products in good enantiomeric excesses. Steric effects and torsional interactions in the corresponding approaches account for the observed pi-facial diastereoselectivities

  在环己烯环的C-5位带有氧取代基和/或甲基的手性外消旋乙烯基环己烯2与对映体纯的（SS）-（2-p-甲苯基亚磺酰基）-1,4进行Diels-Alder反应-萘醌[（+）-1]。多米诺环加成/热解亚砜的消除过程导致形成对映异构体富集的角四环醌抗6和syn-7，这是由外消旋二烯的动力学拆分获得的。在所有情况下，（SS）-（2-对-甲苯基亚磺酰基）-1,4-萘醌从反应性更强的s-顺式构象的较少受阻面反应，形成对映体过量的产物。相应方法中的立体效应和扭转相互作用说明了在两个伙伴处观察到的pi面非对映选择性。
• Enantioselective Diels–Alder Approach to Angucyclinones from(S)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone and Substituted Racemic Vinylcyclohexenes
  作者：M. Carmen Carreño、Antonio Urbano、Jean Fischer

  DOI：10.1002/anie.199716211

  日期：1997.8.18
• Enantioselective Diels–Alder reactions of chiral racemic acyclic dienes with (SS)-2-(p-tolylsulfinyl)-1,4-naphthoquinone
  作者：M.Carmen Carreño、Susana Garcı́a-Cerrada、Antonio Urbano、Claudio Di Vitta

  DOI：10.1016/s0957-4166(98)00323-1

  日期：1998.9

  Enantiopure sulfinylnaphthoquinone (+)-1 reacted with racemic acyclic dienes 2a-f bearing a stereogenic allylic center, through a tandem cycloaddition/pyrolytic sulfenic acid elimination, to afford enantio-enriched compounds 4a-f and 5a-f with good like:unlike selectivities (ca. 75:25) and good enantiomeric excesses (68-82%), arising from the partial kinetic resolution of the racemic dienes. (C) 1998 Elsevier Science Ltd. All rights reserved.