Benzyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate | 871926-94-2

• 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: Benzyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate
• CAS: 871926-94-2
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: AQEMEMKEUSQYDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  503.6±50.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate 在 lithium hydroxide 、 lithium aluminium tetrahydride 、 ammonium cerium(IV) nitrate 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 3.5h， 生成 盐酸氟西汀
  参考文献：
  名称：

  CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines

  摘要：

  A CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines 2Aa-Be to P-amino carbonyl compounds 3Aa-Be and 4Aa-Be in different ratios is described. This facile strategy was also used to synthesize racemic fluoxetine (5). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.039
• 作为产物：
  描述：

  4-羟基-1-哌啶甲酸苄酯 在 四氧化锇 、 N-甲基吲哚酮 作用下， 生成 Benzyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines

  摘要：

  A CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines 2Aa-Be to P-amino carbonyl compounds 3Aa-Be and 4Aa-Be in different ratios is described. This facile strategy was also used to synthesize racemic fluoxetine (5). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.039

文献信息

• Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline
  作者：Meng-Yang Chang、Chun-Li Pai、Yung-Hua Kung

  DOI：10.1016/j.tetlet.2005.10.015

  日期：2005.12

  A straightforward synthesis of (+/-)-coerulescine and (+/-)-horsfiline has been established from 3-formyl-3-phenylpyrridine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (+/-)-coerulescine and ()-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3-plienylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton. (c) 2005 Elsevier Ltd. All rights reserved.
• CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines
  作者：Meng-Yang Chang、Chun-Yu Lin、Chun-Li Pai

  DOI：10.1016/j.tetlet.2006.02.039

  日期：2006.4

  A CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines 2Aa-Be to P-amino carbonyl compounds 3Aa-Be and 4Aa-Be in different ratios is described. This facile strategy was also used to synthesize racemic fluoxetine (5). (c) 2006 Elsevier Ltd. All rights reserved.