3,4-Dimethoxybenzyl phenyl sulfide | 83318-94-9

• 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: 3,4-Dimethoxybenzyl phenyl sulfide
• 英文别名: (3,4-dimethoxybenzyl)(phenyl)sulfane；1,2-Dimethoxy-4-(phenylsulfanylmethyl)benzene
• CAS: 83318-94-9
• 化学式: C₁₅H₁₆O₂S
• 分子量: 260.357
• InChiKey: GJNYHPQECVRRRP-UHFFFAOYSA-N

物化性质

• 沸点：
  381.4±32.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Dimethoxybenzyl phenyl sulfide 在 W-2 Ra-Ni 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 38.5h， 生成 3,4,3',4'-tetramethoxy-9,9'-epoxylignan
  参考文献：
  名称：

  Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutions

  摘要：

  Several natural and unnatural tetrahydrofuran lignans have been synthesized by a convergent approach. Our methodology utilizes a nitrile oxide cycloaddition to dihydrofuran 8 and an enzymatic resolution of alcohols 11 by lipase PS. The lipase-mediated kinetic resolution of alcohols 11 furnished both enantiomers of the lignan precursors 12 and 14 in high optical purity (>99% ee). This is followed by a S(N)2 displacement of tosylates 15 and 18 by alpha-lithiobenzyl phenyl sulfides. In this manner, both enantiomers of 3,4-dibenzyltetrahydrofuran (17a, 20a), 3,4-bis(3-methoxybenzyl)-tetrahydrofuran (17b, 20b), brassilignan (17c, 20c), dehydroxycubebin (17d, 20d), and burseran (17e, 20e) were synthesized in overall yields of 6-16%.

  DOI：

  10.1021/jo00060a037
• 作为产物：
  描述：

  3,4-二甲氧基苄醇 在 盐酸 、 sodium 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 3,4-Dimethoxybenzyl phenyl sulfide
  参考文献：
  名称：

  Pelter, Andrew; Ward, Robert S.; Pritchard, Martyn C., Journal of the Chemical Society. Perkin transactions I, 1988, p. 1615 - 1624

  摘要：

  DOI：

文献信息

• Unusual Cleavage of Ethers by Thiophenol on the Surface of Silica Gel Impregnated with Indium(III) Chloride under Microwave Irradiation: Efficient Procedure for the Synthesis of Thioethers through Transthioetherification
  作者：Brindaban C. Ranu、Sampak Samanta、Alakananda Hajra

  DOI：10.1055/s-2002-31911

  日期：——

  Cyclic and open-chain benzylic ethers undergo cleavage by thiophenol on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation to produce the corresponding di- and monothioethers.

  环状和开链苄醚在掺有氯化铟(III)的硅胶表面，在微波辐照下与硫苯发生裂解，生成相应的二硫醚和单硫醚。
• Visible-Light-Induced Cyclization of Electron-Enriched Phenyl Benzyl Sulfides: Synthesis of Tetrahydrofurans and Tetrahydropyrans
  作者：Wujiong Xia、Wei Li、Chao Yang、Guo-Lin Gao

  DOI：10.1055/s-0035-1561393

  日期：——

  A new approach to the preparation of tetrahydrofurans and tetrahydropyrans through a photoredox catalytic process is described. The introduction of a phenylsulfanyl auxiliary group permits the substrates to be readily oxidized to form cationic intermediates for sequential intramolecular cyclization. The method features mild reaction conditions and operational simplicity.

  描述了一种通过光氧化还原催化过程制备四氢呋喃和四氢吡喃的新方法。苯硫基辅助基团的引入使底物易于氧化以形成用于连续分子内环化的阳离子中间体。该方法反应条件温和，操作简单。
• Dithioacetalization or thioetherification of benzyl alcohols using 9-mesityl-10-methylacridinium perchlorate photocatalyst
  作者：Milan Pramanik、Khokan Choudhuri、Ashis Mathuri、Prasenjit Mal

  DOI：10.1039/d0cc02352c

  日期：——

  We report herein the use of 9-mesityl-10-methylacridinium perchlorate as the visible-light photocatalyst for dithioacetalization or thioetherification of benzyl alcohols in one pot using aerial dioxygen as a terminal oxidant. EPR analysis and Stern–Volmer quenching studies helped to rationalize the single electron transfer (SET) mechanism.

  我们在此报道了使用9-间甲氧基-10-甲基ac啶高氯酸盐作为可见光光催化剂，用于在使用空中二氧作为末端氧化剂的一个罐中对苄醇进行二硫缩醛化或硫醚化。EPR分析和Stern-Volmer淬灭研究有助于合理化单电子转移（SET）机制。
• Synthesis of deoxyisopodophyllotoxin and epiisopodophyllotoxin.
  作者：Andrew Pelter、Robert S. Ward、Martyn C. Pritchard、I. Trevor Kay

  DOI：10.1016/s0040-4039(01)84603-7

  日期：——

  Cyclisation of the tandem conjugate addition products 1-3 by displacement of either the OH or SPh group provides a short efficient synthesis of lignan lactones including compounds of the clinically important podophyllotoxin series.

  通过取代OH或SPh基团而串联的共轭加成产物1-3的环化提供了包括临床上重要的鬼臼毒素系列化合物在内的木脂素内酯的短时有效合成。
• Camphorquinone: a new and efficient oxidant for the preparation of 2-thio-substituted benzothiazoles from alcohols by oxidation-reduction condensation
  作者：Wanchai Pluempanupat、Parinthorn Temyarasilp、Michael Widhalm、Warinthorn Chavasiri

  DOI：10.1080/17415993.2014.907408

  日期：2014.7.4

  A convenient one-pot procedure for the preparation of various 2-thio-substituted benzothiazoles from alcohols and benzothiazole-2-thiol utilizing camphorquinone-mediated oxidation-reduction condensation is disclosed. The condensation between benzothiazole-2-thiol and alkyl diphenylphosphinites, generated in situ from alcohols and chlorodiphenylphosphine, proceeded smoothly in the presence of camphorquinone to furnish the corresponding benzothiazoles in good to moderate yields.[GRAPHICS].