1-benzhydryl-2-propionylpiperidine | 477335-87-8

• 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-benzhydryl-2-propionylpiperidine
• 英文别名: 1-(1-benzhydrylpiperidin-2-yl)propan-1-one
• CAS: 477335-87-8
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: FUBLZRAUQVEFLC-UHFFFAOYSA-N

物化性质

• 沸点：
  416.4±45.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzhydryl-2-propionylpiperidine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (+/-)-erythro-1-benzhydryl-2-hydroxypropylpiperidine 、 (+/-)-erythro-1-benzhydryl-2-hydroxypropylpiperidine
  参考文献：
  名称：

  摘要：

  Reaction of ethyl N-benzhydrylpipecolinate with ethylmagnesium bromide in the presence of catalytic amount of titanium(IV) isopropoxide furnished in a high yield the corresponding hydroxypropyl-substituted piperidine that by treating with alcoholic alkali was quantitatively converted into 1-benzhydryl-2-propionylpiperidine. The reduction in the latter of carbonyl group with lithium aluminum hydride or sodium borohydride in methanol gave rise prevailingly to threo-aminoalcohol. With sodium borohydride in the presence of cerium chloride an erythro-aminoalcohol was the main product. Deprotection of the nitrogen atom from the benzhydryl group of the aminoalcohols obtained provided racemic alpha- and beta-conhydrines.

  DOI：

  10.1023/a:1020359725353
• 作为产物：
  描述：

  1-benzhydryl-2-(1-hydroxycyclopropyl)piperidine 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以97%的产率得到1-benzhydryl-2-propionylpiperidine
  参考文献：
  名称：

  摘要：

  Reaction of ethyl N-benzhydrylpipecolinate with ethylmagnesium bromide in the presence of catalytic amount of titanium(IV) isopropoxide furnished in a high yield the corresponding hydroxypropyl-substituted piperidine that by treating with alcoholic alkali was quantitatively converted into 1-benzhydryl-2-propionylpiperidine. The reduction in the latter of carbonyl group with lithium aluminum hydride or sodium borohydride in methanol gave rise prevailingly to threo-aminoalcohol. With sodium borohydride in the presence of cerium chloride an erythro-aminoalcohol was the main product. Deprotection of the nitrogen atom from the benzhydryl group of the aminoalcohols obtained provided racemic alpha- and beta-conhydrines.

  DOI：

  10.1023/a:1020359725353