Benzyl 4-(1,3-benzodioxol-5-yl)-3,4-dihydroxypiperidine-1-carboxylate | 871926-98-6

• 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 4-(1,3-benzodioxol-5-yl)-3,4-dihydroxypiperidine-1-carboxylate
• 英文别名: benzyl 4-(1,3-benzodioxol-5-yl)-3,4-dihydroxypiperidine-1-carboxylate
• CAS: 871926-98-6
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: PZMJAENFPZRRFA-UHFFFAOYSA-N

物化性质

• 沸点：
  553.7±50.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Benzyl 4-(1,3-benzodioxol-5-yl)-3,4-dihydroxypiperidine-1-carboxylate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以92%的产率得到Benzyl 3-(1,3-benzodioxol-5-yl)-3-formylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.10.015
• 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 、 jones reagent 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 4.5h， 生成 Benzyl 4-(1,3-benzodioxol-5-yl)-3,4-dihydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.10.015

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.