tert-butyl 5-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2,6-dimethylpyridine-3-carboxylate | 1026390-01-1

• 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: tert-butyl 5-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2,6-dimethylpyridine-3-carboxylate
• CAS: 1026390-01-1
• 化学式: C₂₃H₂₈N₂O₄
• 分子量: 396.486
• InChiKey: MUUMRLZDXHCCDV-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 苯基锂 、 tert-butyl 5-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2,6-dimethylpyridine-3-carboxylate 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 20.0h， 生成 3-O-tert-butyl 1-O-ethyl (4S)-5-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2,6-dimethyl-4-phenyl-4H-pyridine-1,3-dicarboxylate 、 3-O-tert-butyl 1-O-ethyl (4R)-5-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2,6-dimethyl-4-phenyl-4H-pyridine-1,3-dicarboxylate
  参考文献：
  名称：

  An Asymmetric Synthesis of 4-Aryl-1,4-dihydropyridines

  摘要：

  Phenyllithium was found to attack preferentially the ester group of 5-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-2,6-dimethylnicotinic acid ethyl ester (6) to give phenyl ketone (7) and diphenylcarbinol (8), despite the directing effect of the oxazoline group. By replacing the ethyl ester in 6 with a bulky tert-butyl ester, the desired 1,4-addition with PhLi to give 4-phenyldihydropyridine derivative (12) in 67% was observed. As a chiral version of the above reaction, 2-[5-(tert-butoxycarbonyl)-2,6-dimethyl-3-pyridyl]-4-(S)-methoxymethyl-5-(S)-phenyl-Delta(2)-oxazoline (13) reacted with PhLi to give 3-(tert-butoxycarbonyl)-2,6-dimethyl-N-ethoxycarbonyl-5-[(4S,5S)-4-methoxymethyl--5-phenyl-4,5-dihydro-oxazol-2-yl]-4-(S)-phenyl-1,4-dihydropyridine (1) and its C-4 epimer (2) in a ratio of 5:1 and a total yield of 54%.

  DOI：

  10.3987/com-96-7565
• 作为产物：
  描述：

  2,6-二甲基吡啶-3,5-二甲酸二乙酯 在 四氯化碳 、 氢氧化钾 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 N,N'-羰基二咪唑 作用下， 以 吡啶 、 乙醇 、 水 、 乙腈 为溶剂， 反应 69.0h， 生成 tert-butyl 5-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2,6-dimethylpyridine-3-carboxylate
  参考文献：
  名称：

  An Asymmetric Synthesis of 4-Aryl-1,4-dihydropyridines

  摘要：

  Phenyllithium was found to attack preferentially the ester group of 5-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-2,6-dimethylnicotinic acid ethyl ester (6) to give phenyl ketone (7) and diphenylcarbinol (8), despite the directing effect of the oxazoline group. By replacing the ethyl ester in 6 with a bulky tert-butyl ester, the desired 1,4-addition with PhLi to give 4-phenyldihydropyridine derivative (12) in 67% was observed. As a chiral version of the above reaction, 2-[5-(tert-butoxycarbonyl)-2,6-dimethyl-3-pyridyl]-4-(S)-methoxymethyl-5-(S)-phenyl-Delta(2)-oxazoline (13) reacted with PhLi to give 3-(tert-butoxycarbonyl)-2,6-dimethyl-N-ethoxycarbonyl-5-[(4S,5S)-4-methoxymethyl--5-phenyl-4,5-dihydro-oxazol-2-yl]-4-(S)-phenyl-1,4-dihydropyridine (1) and its C-4 epimer (2) in a ratio of 5:1 and a total yield of 54%.

  DOI：

  10.3987/com-96-7565

文献信息

• An Asymmetric Synthesis of 4-Aryl-1,4-dihydropyridines
  作者：Chen-Yu Cheng、Jy-Yih Chen、Mei-Jing Lee

  DOI：10.3987/com-96-7565

  日期：——

  Phenyllithium was found to attack preferentially the ester group of 5-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-2,6-dimethylnicotinic acid ethyl ester (6) to give phenyl ketone (7) and diphenylcarbinol (8), despite the directing effect of the oxazoline group. By replacing the ethyl ester in 6 with a bulky tert-butyl ester, the desired 1,4-addition with PhLi to give 4-phenyldihydropyridine derivative (12) in 67% was observed. As a chiral version of the above reaction, 2-[5-(tert-butoxycarbonyl)-2,6-dimethyl-3-pyridyl]-4-(S)-methoxymethyl-5-(S)-phenyl-Delta(2)-oxazoline (13) reacted with PhLi to give 3-(tert-butoxycarbonyl)-2,6-dimethyl-N-ethoxycarbonyl-5-[(4S,5S)-4-methoxymethyl--5-phenyl-4,5-dihydro-oxazol-2-yl]-4-(S)-phenyl-1,4-dihydropyridine (1) and its C-4 epimer (2) in a ratio of 5:1 and a total yield of 54%.