1-<1-(Phenylthio)ethyl>pyrrolidin-2-one | 91640-19-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-<1-(Phenylthio)ethyl>pyrrolidin-2-one
• 英文别名: 1-(1-phenylsulfanyl-ethyl)-pyrrolidin-2-one；1-[(1-phenylthio)ethyl]-2-pyrrolidinone；1-(1-Phenylmercapto-aethyl)-2-oxo-pyrrolidin；1-(1-Phenylmercapto-ethyl)-2-oxo-pyrrolidin；1-(1-Phenylsulfanylethyl)pyrrolidin-2-one
• CAS: 91640-19-6
• 化学式: C₁₂H₁₅NOS
• 分子量: 221.323
• InChiKey: KQMPABVRZDFOPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 在 对甲苯磺酸 、 zinc dibromide 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 6.17h， 生成 1-<1-(Phenylthio)ethyl>pyrrolidin-2-one
  参考文献：
  名称：

  New Synthesis of Amines and Amides Mediated by Additions of Benzotriazole to Enamines and Enamides and Transformations of the Adducts

  摘要：

  可以获得类型为 N-C-Bt 的加成物，其中氮原子来源于 N-乙烯基非碱性杂环 NH 化合物或次级酰胺，或其中中心碳原子通过将苯并三唑加到烯胺或烯酰胺中而来源于酮。因此，9-乙烯基卡巴唑、1-乙烯基吡咯烷-2-酮和 1-(1-乙基丙-1-烯基)吡咯烷提供了相应的 N-(1-苯并三唑基烷基)取代化合物，这些化合物可以通过多种方法进行烷基化，产率良好。通过这种方式，苯并三唑介导的胺和酰胺的合成范围显著扩大。

  DOI：

  10.1055/s-1992-26362

文献信息

• Regioselective Hydrothiolation of Alkenes Bearing Heteroatoms with Thiols Catalyzed by Palladium Diacetate
  作者：Taichi Tamai、Akiya Ogawa

  DOI：10.1021/jo500586a

  日期：2014.6.6

  examples of transition-metal-catalyzed hydrothiolation of alkynes, the corresponding catalytic addition of thiols to alkenes has remained undeveloped. However, a novel Pd-catalyzed addition of thiols to alkenes bearing a heteroatom, such as oxygen and nitrogen, is found to proceed under mild conditions to give the corresponding Markovnikov adducts, regioselectively, in good yields.

  与过渡金属催化的炔烃氢硫醇化反应的许多实例形成鲜明对比的是，尚未开发出相应的硫醇向烯烃的催化加成反应。然而，发现在温和的条件下，新型的钯催化的硫醇向带有杂原子的烯烃（如氧和氮）进行新型的Pd催化加成反应，可以区域选择性地以高收率得到相应的马尔可夫尼科夫加合物。
• Visible light photoredox-catalyzed hydrothiolation of enamides and enecarbamates
  作者：Eliezer Barman、Jason Hourizadeh、Daniel Lim

  DOI：10.1016/j.tetlet.2020.152201

  日期：2020.8

  An efficient visible light photoredox-catalyzed, Markovnikov selective, hydrothiolation reaction of enamides and enecarbamates is presented. This protocol is mild and operationally simple. This process provides access to N,S-acetal products from available thiols and a variety of enamides and enecarbamates. (C) 2020 Elsevier Ltd. All rights reserved.
• Wu, Guai Li; Liu, Jian; Wei, Yanli, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 5, p. 656 - 661
  作者：Wu, Guai Li、Liu, Jian、Wei, Yanli、Chen, Yong Jiang、Min, Long

  DOI：——

  日期：——
• New Synthesis of Amines and Amides Mediated by Additions of Benzotriazole to Enamines and Enamides and Transformations of the Adducts
  作者：Alan R. Katritzky、Simona Jurczyk、Bogumila Rachwal、Stanislaw Rachwal、Irina Shcherbakova、Konstantina Yannakopoulou

  DOI：10.1055/s-1992-26362

  日期：——

  Adducts of type N-C-Bt can be obtained in which the nitrogen atom is derived from an N-vinyl non-basic heterocyclic NH compound or a secondary amide, or in which the central carbon is derived from a ketone by the addition of benzotriazole to an enamine or enamide. Thus, 9-vinylcarbazole, 1-vinylpyrrolidin-2-one and 1-(1-ethylprop-1-enyl)pyrrolidine afforded the corresponding N-(1-benzotriazolylalkyl)-substituted compounds which could be alkylated by various methods in good yield. The range of benzotriazole mediated syntheses of amines and amides is significantly extended in this way.

  可以获得类型为 N-C-Bt 的加成物，其中氮原子来源于 N-乙烯基非碱性杂环 NH 化合物或次级酰胺，或其中中心碳原子通过将苯并三唑加到烯胺或烯酰胺中而来源于酮。因此，9-乙烯基卡巴唑、1-乙烯基吡咯烷-2-酮和 1-(1-乙基丙-1-烯基)吡咯烷提供了相应的 N-(1-苯并三唑基烷基)取代化合物，这些化合物可以通过多种方法进行烷基化，产率良好。通过这种方式，苯并三唑介导的胺和酰胺的合成范围显著扩大。