(3-hydroxy-4-iodo-phenyl)-piperidin-1-yl-methanone | 913484-66-9

• 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: (3-hydroxy-4-iodo-phenyl)-piperidin-1-yl-methanone
• 英文别名: (3-hydroxy-4-iodophenyl)-piperidin-1-ylmethanone
• CAS: 913484-66-9
• 化学式: C₁₂H₁₄INO₂
• 分子量: 331.153
• InChiKey: OQLCSVFETTUQJW-UHFFFAOYSA-N

物化性质

• 沸点：
  408.7±35.0 °C(Predicted)
• 密度：
  1.697±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-hydroxy-4-iodo-phenyl)-piperidin-1-yl-methanone 在 四丁基氯化铵 、 palladium diacetate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 67.0h， 生成 (1S,2R)-2-amino-1-phenylpropan-1-ol;(3S)-3-benzyl-6-(piperidine-1-carbonyl)-2H-1-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
• 作为产物：
  描述：

  哌啶 、 3-羟基-4-碘苯甲酸 在 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-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以56%的产率得到(3-hydroxy-4-iodo-phenyl)-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

文献信息

• Heterocyclic modulators of cannabinoid receptors
  申请人：THE CLEVELAND CLINIC FOUNDATION

  公开号：US09339486B2

  公开（公告）日：2016-05-17

  Heterocyclic compounds which modulate cannabinoid receptors are presented. Pharmaceutical compositions containing these compounds, methods of using these compounds as modulators of cannabinoid receptors and processes for synthesizing these compounds are also described herein.

  呈现了调节大麻素受体的杂环化合物。本文还描述了含有这些化合物的药物组合物、使用这些化合物作为大麻素受体调节剂的方法以及合成这些化合物的过程。