deoxyamphimedine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: deoxyamphimedine
• 英文别名: 5-methyl-10,20-diaza-5-azoniapentacyclo[11.7.1.02,7.09,21.014,19]henicosa-1(20),2(7),3,5,9,11,13(21),14,16,18-decaen-8-one
• 化学式: C₁₉H₁₂N₃O
• 分子量: 298.324
• InChiKey: AMLWLOWGKNZNNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  deoxyamphimedine 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 0.58h， 以92%的产率得到10-甲基-8H-苯并[b]吡啶并[4,3,2-De][1,8]菲咯啉-8,11(10H)-二酮
  参考文献：
  名称：

  Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine

  摘要：

  Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxyamphimedine and deoxyamphimedine. Oxidation of the latter using either K-3[Fe(CN)(6)] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyampbimedine and amphimedine.

  DOI：

  10.1021/acs.joc.5b02312
• 作为产物：
  描述：

  色胺盐酸盐 在 盐酸 、 cerium(III) chloride heptahydrate 、 氢溴酸 、 氧气 、 溶剂黄146 、 二甲基亚砜 、 sodium hydroxide 、 silver(l) oxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 31.75h， 生成 deoxyamphimedine
  参考文献：
  名称：

  Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine

  摘要：

  Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxyamphimedine and deoxyamphimedine. Oxidation of the latter using either K-3[Fe(CN)(6)] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyampbimedine and amphimedine.

  DOI：

  10.1021/acs.joc.5b02312

文献信息

• Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine
  作者：Iman M. Khalil、David Barker、Brent R. Copp

  DOI：10.1021/acs.joc.5b02312

  日期：2016.1.4

  Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxyamphimedine and deoxyamphimedine. Oxidation of the latter using either K-3[Fe(CN)(6)] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyampbimedine and amphimedine.