3-benzyl-6-(piperidine-1-carbonyl)-2,3-dihydro-benzofuran-3-carboxylic acid | 1380595-47-0

• 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: 3-benzyl-6-(piperidine-1-carbonyl)-2,3-dihydro-benzofuran-3-carboxylic acid
• 英文别名: 3-benzyl-6-(piperidine-1-carbonyl)-2H-1-benzofuran-3-carboxylic acid
• CAS: 1380595-47-0
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: SYROBRUYRDMASC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-6-(piperidine-1-carbonyl)-2,3-dihydro-benzofuran-3-carboxylic acid 在 三乙胺 、 氯甲酸甲酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (R)-(3-benzyl-3-hydroxymethyl-2,3-dihydro-benzofuran-6-yl)-piperidin-1-yl-methanone
  参考文献：
  名称：

  A synthetic approach for (S)-(3-benzyl-3-methyl-2,3-dihydro-benzofuran-6-yl)-piperidin-1-yl-methanone, a selective CB2 receptor agonist

  摘要：

  (S)-(3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-yl)-piperidin-1-yl-methanone, a selective CB2 receptor agonist, was obtained from 3-hydroxy-4-iodo benzoic acid in nine steps with 97.4% ee and 3.4% total yield, which involved palladium catalyzed tandem intramolecular Heck/Suzuki cross coupling reaction, chemical resolution with (+)-norephedrine and Wolf-Kishner reaction as the key steps. (S)-(3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-yl)-piperidin-1-yl-methanone will be evaluated in vivo studies and this approach will be applied in the optimization process of CB2 receptor agonist. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.076
• 作为产物：
  描述：

  哌啶 在 四丁基氯化铵 、 palladium diacetate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 83.0h， 生成 3-benzyl-6-(piperidine-1-carbonyl)-2,3-dihydro-benzofuran-3-carboxylic acid
  参考文献：
  名称：

  A synthetic approach for (S)-(3-benzyl-3-methyl-2,3-dihydro-benzofuran-6-yl)-piperidin-1-yl-methanone, a selective CB2 receptor agonist

  摘要：

  (S)-(3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-yl)-piperidin-1-yl-methanone, a selective CB2 receptor agonist, was obtained from 3-hydroxy-4-iodo benzoic acid in nine steps with 97.4% ee and 3.4% total yield, which involved palladium catalyzed tandem intramolecular Heck/Suzuki cross coupling reaction, chemical resolution with (+)-norephedrine and Wolf-Kishner reaction as the key steps. (S)-(3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-yl)-piperidin-1-yl-methanone will be evaluated in vivo studies and this approach will be applied in the optimization process of CB2 receptor agonist. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.076