2-(p-tolylthio)thiazole | 1136099-65-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(p-tolylthio)thiazole
• 英文别名: 2-(4-Methylphenyl)sulfanyl-1,3-thiazole
• CAS: 1136099-65-4
• 化学式: C₁₀H₉NS₂
• 分子量: 207.32
• InChiKey: RRBYIXOWAKAATA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-tolylthio)thiazole 在 三氟化硼乙醚 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-(1-(p-tolylthio)-3-(trimethylsilyl)propan-2-yl)thiazol-2(3H)-one
  参考文献：
  名称：

  NucleophilicOrthoAllylation of Aryl and Heteroaryl Sulfoxides

  摘要：

  Aryl and heteroaryl sulf oxides undergo ortho allylation upon treatment with Tf2O and allyisilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods Including Kumada-Corriu cross-coupling of the organosulfanyl group.

  DOI：

  10.1021/ol2025197
• 作为产物：
  描述：

  2-溴噻唑 、 sodium 4-methylbenzenesulfinate 在 氯化镍二甲氧基乙烷 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 水 、 4,4'-二叔丁基-2,2'-二吡啶 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以81%的产率得到2-(p-tolylthio)thiazole
  参考文献：
  名称：

  通过镍/光氧化还原双催化与亚磺酸盐脱氧 C-S 键偶联

  摘要：

  芳基卤化物和硫醇形成的 C-S 键已在各种催化体系下得到很好的证实。在这项工作中，在无碱和无外部还原剂的条件下，通过可见光诱导的光/镍双催化，用户友好的亚磺酸盐被用作 C-S 偶联中的有效亚磺酰化试剂。获得了大量芳基硫醚产品，具有高选择性和对各种功能的高耐受性。

  DOI：

  10.1021/acs.orglett.2c00478

文献信息

• [EN] SULFONYL ARYL HYDROXAMATES AND THEIR USE AS MATRIX METALLOPROTEASE INHIBITORS<br/>[FR] SULFONYL ARYL HYDROXAMATES ET LEUR UTILISATION COMME INHIBITEURS DES METALLOPROTEASES MATRICIELLES
  申请人：PHARMACIA CORP

  公开号：WO2003007954A2

  公开（公告）日：2003-01-30

  The invention is directed to sulfonyl aromatic hydroxamic acid compounds and salts thereof that, inter alia, inhibit matrix metalloprotease (MMP) activity and/or aggrecanase activity. In some particularly preferred embodiments, the compound corresponds in structure to one of the following formulas: (I) (II) wherein W2, the R groups, and -A-R-E-Y are described in more detail in Applicants'specification. This invention also is directed to a process that comprises administering such a compound or pharmaceutically acceptable salt thereof to a host animal having a condition associated with MMP activity.
• Nucleophilic<i>Ortho</i>Allylation of Aryl and Heteroaryl Sulfoxides
  作者：Andrew J. Eberhart、Jason E. Imbriglio、David J. Procter

  DOI：10.1021/ol2025197

  日期：2011.11.4

  Aryl and heteroaryl sulf oxides undergo ortho allylation upon treatment with Tf2O and allyisilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods Including Kumada-Corriu cross-coupling of the organosulfanyl group.
• Deoxygenative C–S Bond Coupling with Sulfinates via Nickel/Photoredox Dual Catalysis
  作者：Shuai Zhong、Zhiwei Zhou、Feng Zhao、Guojiang Mao、Guo-Jun Deng、Huawen Huang

  DOI：10.1021/acs.orglett.2c00478

  日期：2022.3.11

  The C–S bond formation from aryl halides and thiols has been well established under various catalytic systems. In this work, user-friendly sulfinates have been exploited as an efficient sulfenylating reagent in the C–S couplings through visible-light-induced photo/nickel dual catalysis under base- and external reductant-free conditions. A large number of aryl sulfide products were accessed with high

  芳基卤化物和硫醇形成的 C-S 键已在各种催化体系下得到很好的证实。在这项工作中，在无碱和无外部还原剂的条件下，通过可见光诱导的光/镍双催化，用户友好的亚磺酸盐被用作 C-S 偶联中的有效亚磺酰化试剂。获得了大量芳基硫醚产品，具有高选择性和对各种功能的高耐受性。