4,4'-bis-methanesulfonyl-biphenyl | 134368-62-0

• 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: 4,4'-bis-methanesulfonyl-biphenyl
• 英文别名: 4,4'-Bis-methansulfonyl-biphenyl；p.p-Diphenylen-bis-methylsulfon；4-(4'-methylsulfonylphenyl)phenyl methyl sulfone；1-methylsulfonyl-4-(4-methylsulfonylphenyl)benzene
• CAS: 134368-62-0
• 化学式: C₁₄H₁₄O₄S₂
• 分子量: 310.395
• InChiKey: SJHGHKOMUPCIPP-UHFFFAOYSA-N

物化性质

• 沸点：
  553.9±50.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-bis-methanesulfonyl-biphenyl 、 叔丁基二甲基硅氧烷基乙醛 生成 (+/-)-N-hydroxy-N-[1-(hydroxymethyl)-2-[[4'-(methylsulfonyl)[1,1'-biphenyl]-4-yl]sulfonyl]ethyl]formamide
  参考文献：
  名称：

  Reverse hydroxamate inhibitors of matrix metalloproteinases

  摘要：

  具有以下化学式的化合物是基质金属蛋白酶抑制剂。还公开了抑制基质金属蛋白酶的组合物和方法，用于在哺乳动物中抑制基质金属蛋白酶。

  公开号：

  US06294573B1
• 作为产物：
  描述：

  4,4'-bis-(methylsulfinyl)biphenyl 在 双氧水 、 溶剂黄146 作用下， 生成 4,4'-bis-methanesulfonyl-biphenyl
  参考文献：
  名称：

  Zincke; Dahm, Chemische Berichte, 1912, vol. 45, p. 3462

  摘要：

  DOI：

文献信息

• Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides
  作者：Daniel A. Everson、Brittany A. Jones、Daniel J. Weix

  DOI：10.1021/ja301769r

  日期：2012.4.11

  general method is presented for the synthesis of alkylated arenes by the chemoselective combination of two electrophilic carbons. Under the optimized conditions, a variety of aryl and vinyl bromides are reductively coupled with alkyl bromides in high yields. Under similar conditions, activated aryl chlorides can also be coupled with bromoalkanes. The protocols are highly functional-group tolerant (−OH,

  提出了通过两个亲电碳的化学选择性组合合成烷基化芳烃的一般方法。在优化的条件下，各种芳基和乙烯基溴化物以高产率与烷基溴化物还原偶联。在类似条件下，活化的芳基氯也可以与溴代烷烃偶联。该协议具有高度的官能团耐受性（-OH、-NHTs、-OAc、-OTs、-OTf、-COMe、-NHBoc、-NHCbz、-CN、-SO2Me），并且反应在台式上组装，无需排除空气或湿气的特殊预防措施。该反应显示出与传统交叉偶联反应不同的化学选择性，例如铃木-宫浦反应、斯蒂尔反应和日山-丹麦反应。带有亲电和亲核碳的底物导致亲电碳 (R-X) 处的选择性偶联，并且在亲核碳 (R-[M]) 处不发生有机硼 (-Bpin)、有机锡 (-SnMe3) 和有机硅的反应(-SiMe2OH) 含有机卤化物 (X–R–[M])。Hammett 研究表明，σ 和 σ(-) 参数与取代芳基溴化物与溴代烷烃的相对反应速率呈线性相关。这些相关性
• Cobalt-Catalyzed Electrophilic Amination of Arylzincs with<i>N</i>-Chloroamines
  作者：Xin Qian、Zailu Yu、Audrey Auffrant、Corinne Gosmini

  DOI：10.1002/chem.201300229

  日期：2013.5.10

  Roles reversed: An efficient cobalt‐catalyzed electrophilic amination of arylzinc reagents has been achieved. A variety of functionalized arylzincs and N‐chloroamines were coupled under mild conditions (see scheme). Both secondary and tertiary arylamines were obtained in moderate to excellent yields.

  角色颠倒：已实现了高效的钴催化芳基锌试剂的亲电子胺化反应。各种功能化的芳基锌和N-氯胺在温和的条件下偶联（参见方案）。仲和叔芳基胺均以中等至优异的产率获得。
• Copper Powder and Pd(II) Salts Triggered One-Pot Aromatic Halide Homocoupling via a Radical Pathway
  作者：Chen Li、Yumeng Shi、Quan Chen、Kun Zhang、Guang Yang

  DOI：10.1021/acs.joc.2c02717

  日期：2023.2.17

  this work, a bimetallic system was demonstrated, referring to stoichiometric copper powder in the presence of a catalytic amount of Pd(OAc)2, which contributed to delivering various symmetric/asymmetric (sp2)C–(sp2)C species. It has been proposed that the coupling process might be promoted via radicals produced by redox between Cu(0) and Pd(IV) species in the heating system. Increasing examples demonstrated

  (sp 2 )C–(sp 2 )C 键形成是目标合成以及材料和药物生产中最实用的技术之一。联芳基化合物通常与芳基卤化物或拟卤化物偶联而成，需要制备有机金属试剂，效率低，原子经济性差。可以采用经典的 Ullmann 反应直接从芳族卤化物合成联芳基化合物。然而，极高的温度要求限制了该方法在制造中的使用。同时，该机制引发了经典氧化还原反应和涉及自由基的氧化还原反应之间的广泛争论。在这项工作中，展示了一种双金属系统，指的是在催化量的 Pd(OAc) 存在下的化学计量铜粉2，这有助于提供各种对称/不对称 (sp 2 )C–(sp 2 )C 物种。有人提出，耦合过程可能通过加热系统中 Cu(0) 和 Pd(IV) 物种之间的氧化还原产生的自由基来促进。越来越多的例子证明了这种方法对官能团中的芳基溴具有良好的耐受性。
• An Improved Synthesis of the Free Base and Diglycolate Salt of CEP-33779; A Janus Kinase 2 Inhibitor
  作者：Daniel V. Levy、Joseph A. Sclafani、Roger P. Bakale

  DOI：10.1021/acs.oprd.6b00311

  日期：2016.12.16

  CEP-33779 is a triazole that has been reported to show highly selective inhibition of Janus kinase 2 (JAIC2). An efficient process to form CEP-33779 will be presented that uses multiple palladium couplings to provide the drug substance in a convergent manner. The existing medicinal chemistry route was modified to avoid chromatographic purification, improve safety, and utilize palladium ligands which are available in quantities amenable to scale-up. Challenges faced during the development of the new process included optimization of conditions for Buchwald-Hartwig and Suzuki couplings, control of homocoupled impurities and removal of residual palladium. In addition, a screen of conditions to form a diglycolate salt of the parent compound are also presented.
• New Chemical Synthesis of Functionalized Arylzinc Compounds from Aromatic or Thienyl Bromides under Mild Conditions Using a Simple Cobalt Catalyst and Zinc Dust
  作者：Hyacinthe Fillon、Corinne Gosmini、Jacques Périchon

  DOI：10.1021/ja0289494

  日期：2003.4.1

  A new chemical method for the preparation of arylzinc intermediates is described in acetonitrile, on the basis of the activation of aryl bromides by low-valent cobalt species arising from the reduction of cobalt halide by zinc dust. This procedure allows for the synthesis of a variety of functionalized aryl- and thienylzinc species in good to excellent yields. The versatility and the simplicity of that original method represent an alternative to most known procedures.