methyl-2-(4-chlorobutyl)-1-(3,4-dimethoxybenzyl)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate | 1245528-00-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl-2-(4-chlorobutyl)-1-(3,4-dimethoxybenzyl)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate
• 英文别名: methyl 2-(4-chlorobutyl)-1-[(3,4-dimethoxyphenyl)methyl]-4-oxo-3H-pyridine-2-carboxylate
• CAS: 1245528-00-0
• 化学式: C₂₀H₂₆ClNO₅
• 分子量: 395.883
• InChiKey: DGOPEIFPTBUZTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  methyl-2-(4-chlorobutyl)-1-(3,4-dimethoxybenzyl)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate 在 sodium amide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 以87%的产率得到(4aS,8aR)-methyl-1-(3,4-dimethoxybenzyl)-4-oxo-1,4,4a,5,6,7,8,8a-octahydroquinoline-8a-carboxylate
  参考文献：
  名称：

  Synthesis of cylindricine C and a formal synthesis of cylindricine A

  摘要：

  This paper reports the synthesis of the alkaloid natural product (+/-)-cylindricine C, in addition to a formal synthesis of (+/-)-cylindricine A. The key step in our sequence is the (ipso) regioselective addition of an alkyl Grignard reagent to a C-2 substituted pyridinium salt to generate the dihydropyridone core of the alkaloid targets. After cyclisation to form the A and C rings of the cyclindricines the net outcome is a short (13 steps) synthesis of this natural product. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.05.044
• 作为产物：
  描述：

  1-(3,4-dimethoxybenzyl)-4-methoxy-2-(methoxycarbonyl)pyridinium bromide salt 、 magnesium,1-chlorobutane,bromide 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.58h， 以64%的产率得到methyl-2-(4-chlorobutyl)-1-(3,4-dimethoxybenzyl)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate
  参考文献：
  名称：

  Synthesis of cylindricine C and a formal synthesis of cylindricine A

  摘要：

  This paper reports the synthesis of the alkaloid natural product (+/-)-cylindricine C, in addition to a formal synthesis of (+/-)-cylindricine A. The key step in our sequence is the (ipso) regioselective addition of an alkyl Grignard reagent to a C-2 substituted pyridinium salt to generate the dihydropyridone core of the alkaloid targets. After cyclisation to form the A and C rings of the cyclindricines the net outcome is a short (13 steps) synthesis of this natural product. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.05.044

文献信息

• Synthesis of cylindricine C and a formal synthesis of cylindricine A
  作者：Timothy J. Donohoe、Ptoton M. Brian、Gráinne C. Hargaden、Timothy J.C. O’Riordan

  DOI：10.1016/j.tet.2010.05.044

  日期：2010.8

  This paper reports the synthesis of the alkaloid natural product (+/-)-cylindricine C, in addition to a formal synthesis of (+/-)-cylindricine A. The key step in our sequence is the (ipso) regioselective addition of an alkyl Grignard reagent to a C-2 substituted pyridinium salt to generate the dihydropyridone core of the alkaloid targets. After cyclisation to form the A and C rings of the cyclindricines the net outcome is a short (13 steps) synthesis of this natural product. (C) 2010 Published by Elsevier Ltd.