N-((E)-1-Benzyl-2-benzylsulfanyl-vinyl)-formamide

• 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-((E)-1-Benzyl-2-benzylsulfanyl-vinyl)-formamide
• 英文别名: N-[(E)-1-benzylsulfanyl-3-phenylprop-1-en-2-yl]formamide
• 化学式: C₁₇H₁₇NOS
• 分子量: 283.394
• InChiKey: AJBROMODUPBQAP-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-苄基异噻唑 、 溴甲苯 在 ammonium hydroxide 作用下， 生成 N-((E)-1-Benzyl-2-benzylsulfanyl-vinyl)-formamide 、 (E)-2-cyano-3-phenylpropen-1-ylbenzyl thioether 、 (Z)-2-cyano-3-phenylpropen-1-ylbenzyl thioether
  参考文献：
  名称：

  Phototransposition Chemistry of 4-Substituted Isothiazoles. The P₄ Permutation Pathway

  摘要：

  Upon irradiation in the presence of a small quantity of base, 4-substituted isothiazoles undergo photocleavage to yield substituted cyanosulfides, which can be trapped as their benzyl thioether derivatives, and substituted isocyanosulfides. Both products are suggested to arise via initial photocleavage of the sulfur-nitrogen bond, resulting in the formation of a substituted beta-thioformylvinyl nitrene, which can rearrange to the observed cyanosulfide, or cyclize to an undetected thioformylazirine. Deprotonation of the azirine leads directly to the isocyanosulfide. The plight of the isocyanosulfide depends on the C-4 substituent. If the substituent is aromatic, the isocyanosulfide is reprotonated at the isocyanide carbon and spontaneously cyclizes to a 4-substituted thiazole, the observed transposition product. If the substituent is not aromatic, the isocyanosulfide is reprotonated at sulfur and the resulting species has a higher energy barrier to cyclization. In these cases, the isocyanosulfides can be observed spectroscopically and can be trapped as their N-formylaminobenzyl thioether derivatives.

  DOI：

  10.1021/jo980936e

文献信息

• Phototransposition Chemistry of 4-Substituted Isothiazoles. The P₄ Permutation Pathway
  作者：James W. Pavlik、Pakamas Tongcharoensirikul、Kathleen M. French

  DOI：10.1021/jo980936e

  日期：1998.8.1

  Upon irradiation in the presence of a small quantity of base, 4-substituted isothiazoles undergo photocleavage to yield substituted cyanosulfides, which can be trapped as their benzyl thioether derivatives, and substituted isocyanosulfides. Both products are suggested to arise via initial photocleavage of the sulfur-nitrogen bond, resulting in the formation of a substituted beta-thioformylvinyl nitrene, which can rearrange to the observed cyanosulfide, or cyclize to an undetected thioformylazirine. Deprotonation of the azirine leads directly to the isocyanosulfide. The plight of the isocyanosulfide depends on the C-4 substituent. If the substituent is aromatic, the isocyanosulfide is reprotonated at the isocyanide carbon and spontaneously cyclizes to a 4-substituted thiazole, the observed transposition product. If the substituent is not aromatic, the isocyanosulfide is reprotonated at sulfur and the resulting species has a higher energy barrier to cyclization. In these cases, the isocyanosulfides can be observed spectroscopically and can be trapped as their N-formylaminobenzyl thioether derivatives.