N,N-dibenzyl-1-cyclohexenecarbothioamide | 132118-19-5

• 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: N,N-dibenzyl-1-cyclohexenecarbothioamide
• 英文别名: 1-Cyclohexene-1-carbothioamide, N,N-bis(phenylmethyl)-；N,N-dibenzylcyclohexene-1-carbothioamide
• CAS: 132118-19-5
• 化学式: C₂₁H₂₃NS
• 分子量: 321.486
• InChiKey: MPRRGKPTEIOFQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyl-1-cyclohexenecarbothioamide 以 solid 为溶剂， 反应 2.0h， 以96%的产率得到(R)-1-benzyl-4-phenylazetidine-2-thione-3-spiro-1'-cyclohexane
  参考文献：
  名称：

  Crystal-to-Crystal Solid-State Photochemistry:  Absolute Asymmetric β-Thiolactam Synthesis from an Achiral α,β-Unsaturated Thioamide

  摘要：

  DOI：

  10.1021/ja961878m
• 作为产物：
  描述：

  Cyclohex-1-enecarboxylic acid dibenzylamide 在 劳森试剂 作用下， 生成 N,N-dibenzyl-1-cyclohexenecarbothioamide
  参考文献：
  名称：

  Crystal-to-Crystal Solid-State Photochemistry:  Absolute Asymmetric β-Thiolactam Synthesis from an Achiral α,β-Unsaturated Thioamide

  摘要：

  DOI：

  10.1021/ja961878m

文献信息

• Crystalline-State Photoisomerization of<i>α</i>,<i>β</i>-Unsaturated Thioamide Analyzed by X-rays
  作者：Takaaki Hosoya、Takashi Ohhara、Hidehiro Uekusa、Yuji Ohashi

  DOI：10.1246/bcsj.75.2147

  日期：2002.10

  When a crystal of N,N-dibenzyl-1-cyclohexenecarbothioamide was exposed to UV light at 263 K, the cell dimensions were gradually changed with retention of the single crystal form. Since the crystal gradually decomposed after 330 h, the irradiation was stopped and the structure was analyzed by X-rays. The thioamide molecule was converted by 65.0% to the thiolactam molecule. The thioamide and thiolactam molecules were observed as a disordered structure in the crystal. The disordered structure clearly indicates that the hydrogen atom of one of the benzyl groups is extracted by one of the olefin carbon atoms of the cyclohexenyl group and that the benzyl carbon atom makes a bond with another olefin carbon to form a thiolactam ring. The mechanism of the ring formation and the chirality of the produced thiolactam are well explained from the reaction cavity.

  当 N,N-二苄基-1-环己烯硫代甲酰胺晶体暴露于 263 K 的紫外光下时，晶胞尺寸逐渐发生变化，同时保留单晶形式。由于330小时后晶体逐渐分解，因此停止照射并通过X射线分析结构。 65.0%的硫代酰胺分子转化为硫代内酰胺分子。观察到硫代酰胺和硫代内酰胺分子在晶体中呈无序结构。无序结构清楚地表明，一个苄基的氢原子被环己烯基的一个烯烃碳原子萃取，并且该苄基碳原子与另一个烯烃碳形成键合形成硫代内酰胺环。反应腔很好地解释了成环机制和生成的硫内酰胺的手性。