1-benzhydryl-2-(1-hydroxycyclopropyl)piperidine | 477335-86-7

• 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-(1-hydroxycyclopropyl)piperidine
• 英文别名: 1-(1-benzhydrylpiperidin-2-yl)cyclopropanol；1-(1-Benzhydrylpiperidin-2-yl)cyclopropan-1-ol
• CAS: 477335-86-7
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: IKJWQDKVQNFIJK-UHFFFAOYSA-N

物化性质

• 沸点：
  423.7±45.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  乙基溴化镁 、 ethyl N-benzhydrylpipecolinate 在 titanium(IV) isopropylate 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以77%的产率得到1-benzhydryl-2-(1-hydroxycyclopropyl)piperidine
  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

文献信息

• A Convenient Way for the Conversion of Carboxylic Esters into 2-Substituted Allyl Halides
  作者：Oleg G. Kulinkovich、Yurii Y. Kozyrkov、Andrei V. Bekish、Evgenii A. Matiushenkov、Ivan L. Lysenko

  DOI：10.1055/s-2004-834869

  日期：——

  The preparation of functionalized 2-substituted allyl bromides and chlorides from carboxylic esters is reported. The carboxylic esters were transformed first to 1-substituted cyclopropanols by treating with ethylmagnesium bromide in the presence of titanium alkoxide. Mesylation of the cyclopropanols followed by halide displacement of the sulfonate group to halogen, accompanied by cyclopropyl-allyl rearrangement, affords the required allyl bromides and chlorides.

  报道了由羧酸酯制备官能化2-取代烯丙基溴和氯化物。通过在钛醇盐存在下用乙基溴化镁处理，首先将羧酸酯转化为1-取代的环丙醇。环丙醇的甲磺化，然后用卤化物将磺酸根基团置换为卤素，同时进行环丙基-烯丙基重排，得到所需的烯丙基溴和氯化物。