Benzyl 5-(4-chlorophenyl)-2-hydroxypiperidine-1-carboxylate | 1027303-63-4

• 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 5-(4-chlorophenyl)-2-hydroxypiperidine-1-carboxylate
• CAS: 1027303-63-4
• 化学式: C₁₉H₂₀ClNO₃
• 分子量: 345.826
• InChiKey: ZXFGVGWAJUQNJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzyl 5-(4-chlorophenyl)-2-hydroxypiperidine-1-carboxylate 在 盐酸 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (RS)-5-amino-4-(4-chlorophenyl)pentanoic acid hydrochloride
  参考文献：
  名称：

  Heck arylations of N -acyl-3-pyrroline and N -acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts. Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen and analogues

  摘要：

  Heck arylation of N-acyl-3-pyrrolines and an N-acyl-tetrahydropyridine with aryldiazonium tetrafluoroborates under phosphine-free conditions proceeded smoothly to give alpha-hydroxycarbamates (hemiaminals) or alpha-alkoxycarbamates which were oxidized to the desired gamma- and delta-lactams. Acidic hydrolysis of the gamma-lactams produced a series of arylated GABA derivatives, including baclofen, a useful therapeutic drug. in only three steps with ail overall yield of 63 76%, Starting from N-acyl-tetrahydropyridine, aryl-delta-lactams and higher homologues of baclofen can be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02267-5
• 作为产物：
  描述：

  N-苯甲氧基甲酰基-1,2,5,6-四氢吡啶 、 p-chlorobenzenediazonium tetrafluoroborate 在 palladium diacetate 作用下， 以 水 、 乙腈 为溶剂， 生成 benzyl 3-(4-chlorophenyl)-3,6-dihydro-2H-pyridine-1-carboxylate 、 Benzyl 4-(4-chlorophenyl)-2-hydroxypiperidine-1-carboxylate 、 Benzyl 5-(4-chlorophenyl)-2-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Heck arylations of N -acyl-3-pyrroline and N -acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts. Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen and analogues

  摘要：

  Heck arylation of N-acyl-3-pyrrolines and an N-acyl-tetrahydropyridine with aryldiazonium tetrafluoroborates under phosphine-free conditions proceeded smoothly to give alpha-hydroxycarbamates (hemiaminals) or alpha-alkoxycarbamates which were oxidized to the desired gamma- and delta-lactams. Acidic hydrolysis of the gamma-lactams produced a series of arylated GABA derivatives, including baclofen, a useful therapeutic drug. in only three steps with ail overall yield of 63 76%, Starting from N-acyl-tetrahydropyridine, aryl-delta-lactams and higher homologues of baclofen can be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02267-5