bis((2-methoxyphenyl)thio)methane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: bis((2-methoxyphenyl)thio)methane
• 英文别名: Bis[(2-methoxyphenyl)thio]methane；1-methoxy-2-[(2-methoxyphenyl)sulfanylmethylsulfanyl]benzene
• 化学式: C₁₅H₁₆O₂S₂
• 分子量: 292.423
• InChiKey: BPMUIIZBAVTFIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  硝基甲烷 、 2-甲氧基苯硫酚 在 lithium perchlorate 、 scandium tris(trifluoromethanesulfonate) 作用下， 反应 8.0h， 以71%的产率得到bis((2-methoxyphenyl)thio)methane
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source

  摘要：

  Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)(3) as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.

  DOI：

  10.1021/acs.orglett.0c01831

文献信息

• An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks
  作者：Carolina Silva-Cuevas、Ehecatl Paleo、David F. León-Rayo、J. Armando Lujan-Montelongo

  DOI：10.1039/c8ra04002h

  日期：——

  A new method for the bromomethylation of thiols using paraformaldehyde and HBr/AcOH, minimizes the generation of toxic byproducts. Synthetic utility of α-bromomethyl sulfides was demonstrated through umpolung and free radical chemistry.

  使用对甲醛和HBr/AcOH的新方法对硫醇进行溴甲基化，最大程度减少了有毒副产物的生成。通过反极化和自由基化学展示了α-溴甲基硫醚的合成效用。
• Lewis Acid-Promoted Typical Friedel–Crafts Reactions Using DMSO as a Carbon Source
  作者：Nagaraju Vodnala、Sanjay Singh、Chinmoy Kumar Hazra

  DOI：10.1021/acs.joc.2c01037

  日期：2022.8.5

  This study reports a mild and efficient synthetic protocol for the synthesis of symmetrical and unsymmetrical diarylmethanes (DAMs). Using DMSO as the C1 source and TMSOTf as the Lewis acid promoter, a series of functionalized symmetrical and unsymmetrical DAMs were synthesized in high yields. Gratifyingly, DMSO plays a dual role as a solvent and a C1 source and can also be replaced with its deuterated

  本研究报告了一种用于合成对称和不对称二芳基甲烷 (DAM) 的温和有效的合成方案。使用 DMSO 作为 C 1源和 TMSOTf 作为路易斯酸促进剂，以高产率合成了一系列功能化的对称和非对称 DAM。令人欣慰的是，DMSO 作为溶剂和 C 1源具有双重作用，并且还可以用其氘代对应物 DMSO- d 6代替，从而能够掺入 -CD 2部分进入二芳基甲烷骨架。所开发的方法已应用于具有各种官能团的各种底物，该协议也已扩展到使用普通原料化合物合成抗乳腺癌剂和抗凝剂。此外，已通过对照实验明确证明了假设的机制。
• Sc(OTf)₃-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source
  作者：Dattatraya H. Dethe、Manmohan Shukla、Balu D. Dherange

  DOI：10.1021/acs.orglett.0c01831

  日期：2020.8.7

  Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)(3) as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.