N,N-dimethyl-2-naphthalen-2-yldecanethioamide | 1437311-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-dimethyl-2-naphthalen-2-yldecanethioamide
• CAS: 1437311-35-7
• 化学式: C₂₂H₃₁NS
• 分子量: 341.561
• InChiKey: LFFYCAUNNWMSCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴萘 、 N,N-二甲基癸烷硫代酰胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 三苯基膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以51%的产率得到N,N-dimethyl-2-naphthalen-2-yldecanethioamide
  参考文献：
  名称：

  Pd-catalyzed α-arylation of thioamides

  摘要：

  Thioamides are unique and versatile synthetic building blocks with S, N, and alpha-C three adjacent nucleophile centers, however, they are rarely used as carbon nucleophiles for transition-metal-catalyzed C-C coupling reactions. This Letter describes the first Pd-catalyzed alpha-arylation of thioamides and demonstrated the feasibility of the application of thioamides in coupling chemistry. By the coupling process, a variety of alpha-arylated thioamides were prepared in moderate to good yields under mild reaction conditions, which provides an alternative way to access functionalized thioamides as well as a new synthetic transformation for thioamides. High chemoselectivity for thioamide over amide was observed in the reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.114