tert-butyl 2-(3,4-dihydroxyphenyl)ethylcarbamate ditrifluoroacetate

• 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: tert-butyl 2-(3,4-dihydroxyphenyl)ethylcarbamate ditrifluoroacetate
• 英文别名: styelsamine D ditrifluoroacetate；10-(2-Aminoethyl)-8,14-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaen-12-ol;2,2,2-trifluoroacetic acid
• 化学式: 2C₂HF₃O₂*C₁₇H₁₅N₃O
• 分子量: 505.373
• InChiKey: DXKJBKBMIWWLIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 tert-butyl 2-(3,4-dihydroxyphenyl)ethylcarbamate ditrifluoroacetate 在 溶剂黄146 作用下， 以66%的产率得到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
• 作为产物：
  描述：

  盐酸多巴胺 在 cerium(III) chloride heptahydrate 、 碳酸氢钠 、 溶剂黄146 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.5h， 生成 tert-butyl 2-(3,4-dihydroxyphenyl)ethylcarbamate ditrifluoroacetate
  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