1-(3,4-dimethoxybenzyl)-4-methoxy-2-(methoxycarbonyl)pyridinium bromide salt | 1245527-80-3

• 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: 1-(3,4-dimethoxybenzyl)-4-methoxy-2-(methoxycarbonyl)pyridinium bromide salt
• 英文别名: Methyl 1-[(3,4-dimethoxyphenyl)methyl]-4-methoxypyridin-1-ium-2-carboxylate;bromide
• CAS: 1245527-80-3
• 化学式: Br*C₁₇H₂₀NO₅
• 分子量: 398.254
• InChiKey: ZQQJMWIINPCHQF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.16
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxybenzyl)-4-methoxy-2-(methoxycarbonyl)pyridinium bromide salt 、 1-丙炔溴化镁 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.58h， 以72%的产率得到methyl-1-(3,4-dimethoxybenzyl)-4-oxo-6-(prop-1-ynyl)-1,4,5,6-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
• 作为产物：
  描述：

  3,4-二甲氧基苄基溴 、 4-甲氧基吡啶-2-甲酸甲酯 以 乙醚 为溶剂， 反应 48.0h， 以99%的产率得到1-(3,4-dimethoxybenzyl)-4-methoxy-2-(methoxycarbonyl)pyridinium bromide salt
  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.