1-benzyl-2-(3-hydroxypentan-3-yl)hexahydroazepine | 138154-67-3

• 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: 1-benzyl-2-(3-hydroxypentan-3-yl)hexahydroazepine
• 英文别名: 3-(1-Benzylazepan-2-yl)pentan-3-ol
• CAS: 138154-67-3
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: UTVXPGBEPUVLDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-iodobenzyl)hexahydroazepine 、 3-戊酮 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 various solvent(s) 为溶剂， 以88%的产率得到1-benzyl-2-(3-hydroxypentan-3-yl)hexahydroazepine
  参考文献：
  名称：

  Generation and alkylation of carbanions .alpha. to the nitrogen of amines by a new metallation procedure

  摘要：

  Treatment of a tertiary amine having a pendent o-iodobenzyl group on nitrogen with SmI2 generates alpha-amino organosamarium, which reacts with electrophiles giving the corresponding C-C bound formation products in good yield.

  DOI：

  10.1021/jo00029a001

文献信息

• Generation and alkylation of carbanions .alpha. to the nitrogen of amines by a new metallation procedure
  作者：Masahiro Murakami、Minoru Hayashi、Yoshihiko Ito

  DOI：10.1021/jo00029a001

  日期：1992.1

  Treatment of a tertiary amine having a pendent o-iodobenzyl group on nitrogen with SmI2 generates alpha-amino organosamarium, which reacts with electrophiles giving the corresponding C-C bound formation products in good yield.
• Samarium diiodide mediated alkylation of saturated heterocycles alpha to nitrogen
  作者：Susan E. Booth、Tore Benneche、Kjell Undheim

  DOI：10.1016/0040-4020(95)00081-i

  日期：1995.3

  A method for alpha-alkylation of saturated 5-, 6-, 7- and and 8-membered aza-heterocycles is described. The auxiliary is an o-iodobenzyl group attached at the nitrogen. A radical introduced in the o-position is transferred to the amine alpha-position which subsequently leads to an addition reaction with pentan-3-one.