(Z)-N-benzylhexahydro-4H-azepin-4-one semicarbazone | 134390-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (Z)-N-benzylhexahydro-4H-azepin-4-one semicarbazone
• 英文别名: N-benzylhexahydro-4H-azepin-4-one semicarbazone
• CAS: 134390-79-7
• 化学式: C₁₄H₂₀N₄O
• 分子量: 260.339
• InChiKey: UDTNYJPJYLGSLF-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  (Z)-N-benzylhexahydro-4H-azepin-4-one semicarbazone 在 selenium(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以16%的产率得到6-Benzyl-5,6,7,8-tetrahydro-4H-[1,2,3]selenadiazolo[4,5-d]azepine
  参考文献：
  名称：

  Unusual medium effect on the distribution of 1,2,3-selenadiazole regioisomers in the reaction of N-benzyl-4-homopiperidinone semicarbazone with selenium dioxide

  摘要：

  Four 7-membered-ring, unsymmetrical semicarbazones (1, 4-6) were reacted with selenium dioxide to give 1,2,3-selenadiazole products. Special interest was directed to the regiochemical control obtained. Carbocycle 6 and carbamate 4 provided slightly more ''proximal'' isomer (a; ca. 70%) than ''distal'' isomer (b; ca. 30%), and the ratios were unaffected by the presence of water. Thioether 5 showed a significant bias toward the proximal isomer (8a:8b = ca. 7:1); again, there was essentially no water dependence. Amino compound 1 behaved like 4 and 6 in relatively nonpolar solvents, but the proximal isomer 2a was much more prevalent (75 to > 96%) in polar, protic media. For the case of 1, water dramatically amplified the amount of proximal isomer 2a in ether solvents, from 60-65 to 90-95%, and HOAc (at 23-degrees-C) gave 2a almost exclusively. When the HCl salt of 1 was reacted with selenium dioxide in anhydrous ether solvents, an enhancement of proximal isomer 2a (from 60-65 to ca. 85%) was experienced, but water now had little effect on the isomer ratio. Se-77 NMR measurements were employed to distinguish and quantitate selenadiazole regioisomers.

  DOI：

  10.1021/jo00017a038