S-(p-tolyl) furan-2-carbothioate | 17357-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: S-(p-tolyl) furan-2-carbothioate
• 英文别名: S-(4-methylphenyl) furan-2-carbothioate
• CAS: 17357-39-0
• 化学式: C₁₂H₁₀O₂S
• mdl: MFCD03139312
• 分子量: 218.276
• InChiKey: LGMDWAVLRZKTPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(p-tolyl) furan-2-carbothioate 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 p-methylphenyl dithio-2-furoate
  参考文献：
  名称：

  Aminolysis of aryl dithio-2-thiophenates and dithio-2-furoates in acetonitrile

  摘要：

  The aminolyses of the title substrates with anilines and benzylamines are investigated in acetonitrile. A clean second-order kinetics is obtained with a first-order rate law in the amine concentration, which is uncomplicated by the fast proton transfer step. The large magnitude of rho(z) (rho(1g)) as well as rho(x) (rho(nuc)) together with relatively large positive p(xz) values is consistent with a stepwise mechanism in which thiophenolate ion expulsion from the intermediate is rate limiting. For the reactions of aryl dithio-2-thiophenates with benzylamines the magnitude of rho(x) and rho(z) values is relatively smaller suggesting that both the addition and expulsion of thiophenolate are partially rate determining. Relatively large secondary kinetic isotope effects, k(H)/k(D) greater than or equal to 1.7, with deuterated nucleophiles, support involvement a concurrent proton transfer to the departing thiophenolate ion in the transition state. (C) 1998 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1998)30:11<849::aid-kin7>3.0.co;2-v
• 作为产物：
  描述：

  糠酰胺 在 4-二甲氨基吡啶 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 S-(p-tolyl) furan-2-carbothioate
  参考文献：
  名称：

  Na₂CO₃-promoted thioesterification via N–C bond cleavage of amides to construct thioester derivatives

  摘要：

  通过选择性N-C键断裂构建硫酯的一种温和、高效且无过渡金属催化策略已经开发出来。该策略成功地使用化学计量的Na2CO3作为碱，并以中等至优异的产率提供相应的产物。

  DOI：

  10.1177/1747519819873514

文献信息

• Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis
  作者：Maojie Xuan、Chunlei Lu、Meina Liu、Bo-Lin Lin

  DOI：10.1021/acs.joc.9b00500

  日期：2019.6.21

  thioesterification of carboxylic acids with thiols using nontoxic activation agents is highly desirable. Herein, an efficient and practical protocol using safe and inexpensive industrial waste polymethylhydrosiloxane as the activation agent and K3PO4 with 18-crown-6 as a catalyst is described. Various functional groups on carboxylic acid and thiol substituents can be tolerated by the present system to afford thioesters

  非常需要使用无毒的活化剂将羧酸与硫醇直接硫酯化。在此，描述了一种有效且实用的方案，该方案使用安全且廉价的工业废聚甲基氢硅氧烷作为活化剂，并以18-crown-6作为催化剂的K 3 PO 4。本系统可以耐受羧酸和硫醇取代基上的各种官能团，从而以19-100％的收率提供硫酯。
• InCl₃-Catalyzed Synthesis of 1,2-Dimetallic Compounds by Direct Insertion of Aluminum or Zinc Powder
  作者：Tobias D. Blümke、Thomas Klatt、Konrad Koszinowski、Paul Knochel

  DOI：10.1002/anie.201205169

  日期：2012.9.24

  In‐sertion of metal: Catalytic amounts of InCl3 allow the insertion of aluminum and zinc into aromatic 1,2‐dibromides or 1,2‐bromotriflates (see scheme). These 1,2‐dimetallic species can undergo Cu or Pd‐catalyzed acylations, allylations, or cross‐couplings.

  金属的插入：催化量的InCl 3可使铝和锌插入芳族1,2-二溴化物或1,2-溴三氟甲磺酸酯中（请参阅方案）。这些1,2-双金属物种可能会经历Cu或Pd催化的酰化，烯丙基化或交叉偶联。
• Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical–Radical Coupling to Thioesters
  作者：Ganganna Bogonda、Dilip V. Patil、Hun Young Kim、Kyungsoo Oh

  DOI：10.1021/acs.orglett.9b01218

  日期：2019.5.17

  available starting materials: acid chlorides and sodium sulfinates. The facile generation of acyl radical species under the visible light photoredox conditions allows the formation of thiyl radical species from sodium sulfinates via multiple single electron transfer reactions, where the final acyl radical-thiyl radical coupling has been accomplished. The direct radical–radical coupling strategy offers a mild

  已经开发了一种方便的可见光光氧化还原催化剂，用于从两种容易获得的起始原料：酰氯和亚磺酸钠合成硫酯。在可见光光氧化还原条件下容易地产生酰基基团物种使得可以通过多个单电子转移反应由亚磺酸钠形成硫基基团物种，其中已经完成了最终的酰基基团-噻吩基基团偶联。自由基-自由基直接偶联策略为重要的合成构件（例如硫酯）提供了温和且受控的光化学方法。
• Nickel-Catalyzed Thiocarbonylation of Arylboronic Acids with Sulfonyl Chlorides for the Synthesis of Thioesters
  作者：Xinxin Qi、Zhi-Peng Bao、Xin-Tong Yao、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.0c02541

  日期：2020.8.21

  An interesting procedure for thioester synthesis via nickel-catalyzed thiocarbonylation of arylboronic acid with sulfonyl chlorides as the sulfur source has been explored. Using Mo(CO)6 as a solid CO surrogate and reductant, a broad range of thioesters were obtained in moderate to good yields with good functional group tolerance.

  已经探索了一种有趣的方法，该方法通过以磺酰氯为硫源的镍催化的芳基硼酸的硫代羰基化合成硫酯。使用Mo（CO）6作为固体CO替代物和还原剂，可以以中等至良好的收率获得具有良好官能团耐受性的各种硫酯。
• Platinum-Catalyzed Regio- and Stereoselective Arylthiolation of Internal Alkynes
  作者：Fumikazu Yamashita、Hitoshi Kuniyasu、Jun Terao、Nobuaki Kambe

  DOI：10.1021/ol7025069

  日期：2008.1.1

  Unsymmetrical internal alkynes such as ethyl phenylpropiolate (2b) successfully underwent Pt-catalyzed decarbonylative arylthiolation by thioesters. The regio- and stereoselective insertion of 2b into an S-Pt bond was confirmed by reaction with a platinum complex with an S-Pt-Cl framework.

  不对称的内部炔烃，例如苯丙酸乙酯（2b）已成功地通过硫酯进行了Pt催化的脱羰基芳基硫醇化反应。通过与具有S-Pt-Cl骨架的铂配合物反应，确认了2b在S-Pt键中的区域和立体选择性插入。