3-(m-tolylsulfonyl)thiophene | 1027966-66-0

• 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: 3-(m-tolylsulfonyl)thiophene
• 英文别名: 3-(3-Methylphenyl)sulfonylthiophene
• CAS: 1027966-66-0
• 化学式: C₁₁H₁₀O₂S₂
• 分子量: 238.331
• InChiKey: GZCXQXJRXJEADC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(m-tolylsulfonyl)thiophene 在 氯磺酸 、 五氯化磷 作用下， 反应 0.42h， 生成 4-<(3-methylphenyl)sulfonyl>thiophene-2-sulfonyl chloride
  参考文献：
  名称：

  4-Substituted thiophene- and furan-2-sulfonamides as topical carbonic anhydrase inhibitors

  摘要：

  A series of 4-substituted thiophene- and furan-2-sulfonamides was prepared and was found to possess nanomolar-level potency for inhibition of human carbonic anhydrase II in vitro. Selected examples from this group were further evaluated for their potential to act as topically effective ocular hypotensive agents in the ocular normotensive albino rabbit and the ocular alpha-chymotrypsinized rabbit. Solubility studies in water and pH 7.4 buffer were carried out to estimate the ability of compounds to be formulated in solution. The sensitization potential of key representative structures was determined by in vitro glutathione reactivity studies and guinea pig maximization testing.

  DOI：

  10.1021/jm00099a010
• 作为产物：
  描述：

  bis(3-methylphenyl)disulfide 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.25h， 生成 3-(m-tolylsulfonyl)thiophene
  参考文献：
  名称：

  4-Substituted thiophene- and furan-2-sulfonamides as topical carbonic anhydrase inhibitors

  摘要：

  A series of 4-substituted thiophene- and furan-2-sulfonamides was prepared and was found to possess nanomolar-level potency for inhibition of human carbonic anhydrase II in vitro. Selected examples from this group were further evaluated for their potential to act as topically effective ocular hypotensive agents in the ocular normotensive albino rabbit and the ocular alpha-chymotrypsinized rabbit. Solubility studies in water and pH 7.4 buffer were carried out to estimate the ability of compounds to be formulated in solution. The sensitization potential of key representative structures was determined by in vitro glutathione reactivity studies and guinea pig maximization testing.

  DOI：

  10.1021/jm00099a010

文献信息

• Palladium-Catalyzed Three-Component Diaryl Sulfone Synthesis Exploiting the Sulfur Dioxide Surrogate DABSO
  作者：Edward J. Emmett、Barry R. Hayter、Michael C. Willis

  DOI：10.1002/anie.201305369

  日期：2013.11.25

  SO(2) efficient: A three‐component palladium‐catalyzed coupling of aryl lithium compounds; sulfur dioxide (provided by the easy‐to‐handle solid surrogate, DABSO); and aryl, heteroaryl, and alkenyl (pseudo)halides yields a diverse library of sulfones. An electron‐poor XantPhos‐type ligand suppresses aryl–aryl exchange and is key to obtaining high yields.

  SO（2）高效：芳基锂化合物的三组分钯催化偶联；二氧化硫（由易于处理的固体替代物 DABSO 提供）；和芳基、杂芳基和烯基（伪）卤化物产生不同的砜库。缺电子 XantPhos 型配体抑制芳基-芳基交换，是获得高产率的关键。
• Hartman George D., Halczenko Wasyl, Smith Robert L., Sugrue Michael F., M+, J. Med. Chem., 35 (1992) N 21, S 3822-3831
  作者：Hartman George D., Halczenko Wasyl, Smith Robert L., Sugrue Michael F., M+

  DOI：——

  日期：——
• 4-Substituted thiophene- and furan-2-sulfonamides as topical carbonic anhydrase inhibitors
  作者：George D. Hartman、Wasyl Halczenko、Robert L. Smith、Michael F. Sugrue、Pierre J. Mallorga、Stuart R. Michelson、William C. Randall、Harvey Schwam、John M. Sondey

  DOI：10.1021/jm00099a010

  日期：1992.10

  A series of 4-substituted thiophene- and furan-2-sulfonamides was prepared and was found to possess nanomolar-level potency for inhibition of human carbonic anhydrase II in vitro. Selected examples from this group were further evaluated for their potential to act as topically effective ocular hypotensive agents in the ocular normotensive albino rabbit and the ocular alpha-chymotrypsinized rabbit. Solubility studies in water and pH 7.4 buffer were carried out to estimate the ability of compounds to be formulated in solution. The sensitization potential of key representative structures was determined by in vitro glutathione reactivity studies and guinea pig maximization testing.