N-[(1E)-[(2S)-2,5-diphenyl-3,4-dihydropyridin-1(2H)-yl](phenyl)methylidene]-N-[(1S)-1-(methoxymethyl)-2-methylpropyl]amine | 911694-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[(1E)-[(2S)-2,5-diphenyl-3,4-dihydropyridin-1(2H)-yl](phenyl)methylidene]-N-[(1S)-1-(methoxymethyl)-2-methylpropyl]amine
• 英文别名: N-[(1E)-[(2S)-2,5-diphenyl-3,4-dihydropyridin-1(2H)-yl](phenyl)methylene]-N-[(1S)-1-(methoxymethyl)-2-methylpropyl]amine
• CAS: 911694-22-9
• 化学式: C₃₀H₃₄N₂O
• 分子量: 438.613
• InChiKey: OMTLDDDWYZVUBL-GMMGNPOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-[(1E)-[(2S)-2,5-diphenyl-3,4-dihydropyridin-1(2H)-yl](phenyl)methylidene]-N-[(1S)-1-(methoxymethyl)-2-methylpropyl]amine 在 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 36.0h， 以98%的产率得到N-[(1E)-[(2S,5R)-2,5-diphenylpiperidin-1-yl](phenyl)methylidene]-N-[(1S)-1-(methoxymethyl)-2-methylpropyl]amine
  参考文献：
  名称：

  New Methodology Toward Chiral, Non-Racemic 2,5-cis-Substituted Piperidines via Suzuki Cross-Coupling

  摘要：

  1,2,3,4-Tetrahydropyridines were halogenated upon treatment with iodine to obtain the desired cross-coupling precursors. Diastereoselective hydrogenation of Suzuki cross-coupling adducts allowed the facile asymmetric synthesis of 2,5-cis-substituted piperidines in five steps from readily available pyridine.

  DOI：

  10.1021/ol061415d
• 作为产物：
  描述：

  N-{(1S)-1-[(methoxy)methyl]-2-methylpropyl}-N-{(1E)-phenyl[(2S)-2-phenyl-3,4-dihydropyridin-1(2H)-yl]methylene}amine 在 二(三叔丁基膦)钯 、 potassium tert-butylate 、 碘 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 2-甲基-2-丁醇 为溶剂， 反应 24.0h， 生成 N-[(1E)-[(2S)-2,5-diphenyl-3,4-dihydropyridin-1(2H)-yl](phenyl)methylidene]-N-[(1S)-1-(methoxymethyl)-2-methylpropyl]amine
  参考文献：
  名称：

  New Methodology Toward Chiral, Non-Racemic 2,5-cis-Substituted Piperidines via Suzuki Cross-Coupling

  摘要：

  1,2,3,4-Tetrahydropyridines were halogenated upon treatment with iodine to obtain the desired cross-coupling precursors. Diastereoselective hydrogenation of Suzuki cross-coupling adducts allowed the facile asymmetric synthesis of 2,5-cis-substituted piperidines in five steps from readily available pyridine.

  DOI：

  10.1021/ol061415d

文献信息

• Highly Regioselective Intermolecular Arylation of 1,2,3,4-Tetrahydropyridines
  作者：Guillaume Pelletier、Alexandre Larivée、André B. Charette

  DOI：10.1021/ol8018709

  日期：2008.11.6

  Using a catalytic amount of PdCl2(dppf).CH2Cl2 in combination with Ag3PO4 and NaOAc, a range of arylated 1,2,3,4-tetrahydropyridines are synthesized in good yields and with complete selectivity at the beta-position. The reaction is compatible with a variety of electron-donating and electron-withdrawing aryl iodides as well as with heteroaryl iodides. The application of these tetrahydropyridines toward the synthesis of polysubstituted piperidines is also demonstrated.