(S_S)-5-methyl-2-(p-tolylsulfinyl)-1,4-benzoquinone | 189766-16-3

• 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_S)-5-methyl-2-(p-tolylsulfinyl)-1,4-benzoquinone
• 英文别名: (SS)-2-methyl-5-(p-tolylsulfinyl)-1,4-benzoquinone；(S)S-2-methyl-5-p-tolylsufinyl-1,4-benzoquinone；2-methyl-5-[(S)-(4-methylphenyl)sulfinyl]cyclohexa-2,5-diene-1,4-dione
• CAS: 189766-16-3
• 化学式: C₁₄H₁₂O₃S
• 分子量: 260.313
• InChiKey: DMABXFRIIDUNAZ-SFHVURJKSA-N

物化性质

• 沸点：
  463.8±44.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  反-1,3-戊二烯 、 (S_S)-5-methyl-2-(p-tolylsulfinyl)-1,4-benzoquinone 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到(5S)-2,5-dimethyl-5,8-dihydro-1,4-naphthoquinone
  参考文献：
  名称：

  Asymmetric Diels–Alder reactions of 5-substituted and 5,6-disubstituted (S)-2-(p-tolylsulfinyl)-1,4-benzoquinones with cyclopentadiene and trans-piperylene

  摘要：

  A systematic study of reactions between 5-substituted and 5,6-disubstituted (S)-2-p-tolylsulfinyl-p-benzoquinones and cyclopentadiene or trans-piperylene is reported. Complete regio and pi-facial selectivities are observed. The different behaviours of cyclic and acyclic dienes in the presence of ZnBr2 (cyclopentadiene showed reversed diastereoselection) and the role of BF3 . OEt2 are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00094-4
• 作为产物：
  描述：

  (-)-menthyl p-toluenesulfinate 在 正丁基锂 、 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 3.17h， 生成 (S_S)-5-methyl-2-(p-tolylsulfinyl)-1,4-benzoquinone
  参考文献：
  名称：

  ortho-Directed metallation in the regiocontrolled synthesis of enantiopure 2- and/or 3-substituted (S)S-(p-tolylsulfinyl)-1,4-benzoquinones

  摘要：

  DOI：

  10.1016/s0957-4166(97)00062-1

文献信息

• Synthesis and chiroptical properties of ferrocene-[4]-helicenequinones: kinetic resolution of a planar-chiral diene
  作者：Alfonso Latorre、Antonio Urbano、M. Carmen Carreño

  DOI：10.1039/c1cc12921j

  日期：——

  Both enantiomers of ferrocene [4]-helicenequinone 6, showing planar and helical chiralities, have been synthesized with very high optical purities using, as the key step, a kinetic resolution process between planar-chiral racemic ferrocene diene 2 and enantiopure sulfinyl benzoquinone (S)-3.

  [4]-螺旋醌烯铁的两个对映异构体6，同时展现了平面和螺旋手性，其高光学纯度的合成采用了关键步骤——平面手性外消旋二烯环辛四烯铁2和光学纯度高的亚砜苯醌（S）-3之间的动力学拆分过程。
• Regio- and stereoselectivity in Diels–Alder reactions of 1,2-disubstituted dienes with enantiopure (SS)-(p-tolylsulfinyl)-1,4-benzoquinones
  作者：M.Carmen Carreño、José L Garcı́a Ruano*、Cynthia Z Remor、Antonio Urbano

  DOI：10.1016/s0957-4166(00)00365-7

  日期：2000.11

  Reactions of 1,2-disubstituted dienes 1–3 with enantiopure sulfinylquinones 4–6 occur with similar π-facial diastereoselectivities but reversed regiochemistry under thermal conditions and in the presence of ZnBr2. After spontaneous elimination of the sulfoxide, optically active polycyclic dihydroquinones are formed with ees ranging from 36 to >97%. The regiochemistry of the process is controlled by

  的1,2-二取代的二烯反应1 - 3与对映体纯sulfinylquinones 4 - 6发生类似π-面部非对映选择性，但在热条件下和在ZnBr存在反转区域化学2。自发消除亚砜后，形成旋光性多环二氢醌，其ee含量为36％至> 97％。该方法的区域化学由热反应中C-1处的烷基取代基控制，而在ZnBr 2存在下，C-2处的氧化功能成为主要控制者。
• Enantioselective Synthesis of Four Stereoisomers of Sulfinyl Ferrocenyl Quinones with Central, Planar, and Helical Chirality
  作者：Ana M. del Hoyo、Antonio Urbano、M. Carmen Carreño

  DOI：10.1021/acs.orglett.5b03029

  日期：2016.1.4

  Four stereoisomers of sulfinyl ferrocenyl-substituted helicenequinones having central, planar, and helical elements of chirality were stereoselectively formed, in one step, from reaction between enantiopure sulfinyl ferrocenyl dienes and a sulfinyl quinone. Asymmetric synthesis, kinetic resolution, or chemical resolution processes occurred in sequential cycloaddition, sulfoxide elimination, and partial aromatization steps.
• Regiochemical control in asymmetric Diels-Alder cycloadditions of enantiopure (S)S-(p-tolylsulfinyl)-1,4-benzoquinones with Dane's diene
  作者：M.Carmen Carreño、JoséL García Ruano、Cynthia Z Remor、Antonio Urbano、Jean Fischer

  DOI：10.1016/s0040-4039(97)10439-7

  日期：1997.12

  Enantiopure sulfinylquinones (+)-2 and (+)-3 reacted with Dane's diene 1 under thermal and ZnBr2 Lewis acid conditions with reversal regiochemistry but similar pi-facial diastereoselectivity to afford, after spontaneous elimination of the sulfinyl group, tetracyclic derivatives 4-9. (C) 1997 Elsevier Science Ltd.