(-)-(S)-1,4-dimethoxy-2-(p-tolylsulfinyl)benzene | 134281-63-3

• 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)-1,4-dimethoxy-2-(p-tolylsulfinyl)benzene
• 英文别名: 1,4-dimethoxy-2-[(S)-(4-methylphenyl)sulfinyl]benzene
• CAS: 134281-63-3
• 化学式: C₁₅H₁₆O₃S
• 分子量: 276.356
• InChiKey: MBWCLINLTGDTPV-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-(S)-1,4-dimethoxy-2-(p-tolylsulfinyl)benzene 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以89%的产率得到(S)-1,1,4,4-tetramethoxy-2-p-tolylsulfinylcyclohexa-2,5-diene
  参考文献：
  名称：

  （S）-2-对甲苯亚磺酰基-1,4-苯醌的合成及不对称狄尔斯-阿尔德反应

  摘要：

  光学上纯净的（S）-2-对甲苯基亚磺酰基-1,4-苯醌（5）可通过相应的醌双缩酮4的缩酮化反应轻松获得，该缩酮是通过安徒生式合成方法在2-溴-1,4-二甲氧基苯上合成的（1）然后将所得亚砜进行阳极氧化。环戊二烯与5的Diels-Alder反应发生在C 5 -C 6双亲双键上，显示出高的面部选择性，可以通过使用不同的路易斯酸和总内向选择性将其反转。

  DOI：

  10.1016/s0040-4039(00)99307-9
• 作为产物：
  描述：

  (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 、 对苯二甲醚 在 正己基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以77%的产率得到(-)-(S)-1,4-dimethoxy-2-(p-tolylsulfinyl)benzene
  参考文献：
  名称：

  Quinoides and VEGFR2 TKIs influence the fate of hepatocellular carcinoma and its cancer stem cells

  摘要：

  醌类化合物1-5和VEGFR2 TKIs 6-10在肝细胞癌（HCC）和癌干细胞（HCSCs）中的生物活性进行了研究。醌类化合物3能够根除癌干细胞。

  DOI：

  10.1039/c6md00392c

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。
• 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.
• Photoinduced Conformational Switch of Enantiopure Azobenzenes Controlled by a Sulfoxide
  作者：M. Carmen Carreño、Isabel García、Irene Núñez、Estíbaliz Merino、María Ribagorda、Silvia Pieraccini、Gian Piero Spada

  DOI：10.1021/ja070163o

  日期：2007.6.6

  Two series of enantiopure azobenzenes with a p-tolylsulfoxide at the ortho or meta position with respect to the azo group, have been regioselectively synthesized. Both can act as enantiopure molecular switches showing different structural features owing to the presence of the stereogenic sulfur. The photoisomerization process, studied by UV-vis, circular dichroism (CD), NMR, and chiral HPLC evidenced a double role of the sulfoxide. A transfer of chirality from the sulfoxide to the azo system was observed by CD in both cis and trans-isomers of the meta sulfinyl derivatives 3, whereas this perturbation was evident for the ortho sulfinyl series 7 only in the cis isomer. The NMR study evidenced that the s-cis rigid conformation of the bisaromatic sulfoxide was fixing a different orientation of the overall system in each series both in the trans and cis isomers, by forcing a final U-shaped structure in cis-3 and an S-shaped structure in cis-7. Very different values of specific optical rotations were measured in both trans and cis isomers, also reflecting the existence of distinct chiral entities in the photostationary states. The easy and reversible changes occurring between different conformational states could find applications in the photocontrol of several molecular switches.
• Diastereoselective addition of 2-trimethylsilyloxyfuran to (S)-(+)-2-(p-tolylsulfinyl)-1,4-benzoquinone
  作者：Margaret A Brimble、Letecia J Duncalf、David C.W Reid

  DOI：10.1016/0957-4166(94)00383-m

  日期：1995.1

  The uncatalyzed addition of 2-trimethylsilyloxyfuran to (S)-(+)-2-(p-tolysulfinyl)-1,4-benzoquinone 1 afforded a3.4:1 ratio of the diastereomeric adducts 2:3. Acetonitrile was found to be the optimum solvent whilst the use of Lewis acid catalysts afforded lower overall yields.
• CARRENO, M. CARMEN;RUANO, JOSE L. GARCIA;URBANO, ANTONIO, TETRAHEDRON LETT., 30,(1989) N0, C. 4003-4006
  作者：CARRENO, M. CARMEN、RUANO, JOSE L. GARCIA、URBANO, ANTONIO

  DOI：——

  日期：——