8-O-benzyl 6-O-methyl (2S,7R,8S,8aS)-7-(3-chlorophenyl)-2,5,8a-trimethyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-6,8-dicarboxylate | 174967-49-8

• 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: 8-O-benzyl 6-O-methyl (2S,7R,8S,8aS)-7-(3-chlorophenyl)-2,5,8a-trimethyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-6,8-dicarboxylate
• CAS: 174967-49-8
• 化学式: C₂₆H₂₈ClNO₅
• 分子量: 469.965
• InChiKey: CQKLPLWVYPZKKY-GHCNFNEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-O-benzyl 6-O-methyl (2S,7R,8S,8aS)-7-(3-chlorophenyl)-2,5,8a-trimethyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-6,8-dicarboxylate 在 benzyl(triethyl)ammoniumpermanganate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以20%的产率得到(2S,7R,8S,8aS)-7-(3-Chloro-phenyl)-2,5,8a-trimethyl-3-oxo-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridine-6,8-dicarboxylic acid 8-benzyl ester 6-methyl ester
  参考文献：
  名称：

  Enantiospecific synthesis of dihydropyridines from chiral enamines

  摘要：

  A new asymmetric synthesis of dihydropyridines is described. This methodology is based on the use of chiral aminoalcohols to produce enamines, which were used in the synthesis of enantiopure 2-alkyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridines. The known stereochemistry of these compounds was exploited to obtain 1,4-dihydropyridines with controlled configuration at C-4. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00239-x
• 作为产物：
  描述：

  乙酰丙酮苄酯 以 甲醇 为溶剂， 反应 24.0h， 生成 8-O-benzyl 6-O-methyl (2S,7R,8S,8aS)-7-(3-chlorophenyl)-2,5,8a-trimethyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-6,8-dicarboxylate
  参考文献：
  名称：

  对映纯2,3,8,8a-四氢-7H-恶唑并[3,2-a]吡啶衍生物的合成。

  摘要：

  DOI：

  10.1021/jo9514376

文献信息

• Synthesis of Enantiopure 2,3,8,8a- Tetrahydro-7<i>H</i>-oxazolo[3,2-<i>a</i>]pyridine Derivatives
  作者：Esther Caballero、Pilar Puebla、Manuel Medarde、Mar Sánchez、Miguel A. Salvadó、Santiago García-Granda、Arturo San Feliciano

  DOI：10.1021/jo9514376

  日期：1996.1.1
• Enantiospecific synthesis of dihydropyridines from chiral enamines
  作者：Esther Caballero、Pilar Puebla、Mar Sánchez、Manuel Medarde、Lourdes Morán del Prado、Arturo San Feliciano

  DOI：10.1016/0957-4166(96)00239-x

  日期：1996.7

  A new asymmetric synthesis of dihydropyridines is described. This methodology is based on the use of chiral aminoalcohols to produce enamines, which were used in the synthesis of enantiopure 2-alkyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridines. The known stereochemistry of these compounds was exploited to obtain 1,4-dihydropyridines with controlled configuration at C-4. Copyright (C) 1996 Elsevier Science Ltd