(+/-)-N(1)-acetyl-N(1)-deoxymayfoline | 142037-66-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (+/-)-N(1)-acetyl-N(1)-deoxymayfoline
• 英文别名: 9-Acetyl-2-phenyl-1,5,9-triazacyclotridecan-4-one
• CAS: 142037-66-9
• 化学式: C₁₈H₂₇N₃O₂
• 分子量: 317.431
• InChiKey: HQNCQVDTHUJBKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-phenyl-1,5-diazacyclononan-2-one 在 platinum(IV) oxide 吡啶 、 盐酸 、 氢气 、 sodium ethanolate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 xylene 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 51.0h， 生成 (+/-)-N(1)-acetyl-N(1)-deoxymayfoline
  参考文献：
  名称：

  Synthesis of the spermidine alkaloid (±)-N-acetyl-N(1)-deoxymayfoline

  摘要：

  The total synthesis of the spermidine alkaloid (+/-)-N(1)-acetyl-N(1)-deoxymayfoline ((+/-)-1) was achieved by expansion of rings. The 5-membered cyclic compound 2 was fused with butadiene by intermolecular Diels-Alder cycloaddition. The resulting 7-phenyl-1,6-diazabicyclo[4.3.0]nona-3,7-dien-9-one (4) was reductively cleaved with Raney-Ni in alcoholic KOH to afford the mono-cyclic lactam 6. This was selectively alkylated in high yields to the cyano derivative 7. Reduction of the nitrile group to the amine derivative 8 went smoothly by use of Adam's catalyst in the presence of acid. Intramolecular transamidation was then accomplished by acid catalysis with TsOH to furnish the 13-membered diazalactam 9. The synthesis of (+/-)-1 was completed by the selective acetylation of the more nucleophilic amino group.

  DOI：

  10.1016/s0040-4020(01)92268-9

文献信息

• Synthesis of the spermidine alkaloid (±)-N-acetyl-N(1)-deoxymayfoline
  作者：Bassem F. Tawil、Armin Guggisberg、Manfred Hesse

  DOI：10.1016/s0040-4020(01)92268-9

  日期：1992.1

  The total synthesis of the spermidine alkaloid (+/-)-N(1)-acetyl-N(1)-deoxymayfoline ((+/-)-1) was achieved by expansion of rings. The 5-membered cyclic compound 2 was fused with butadiene by intermolecular Diels-Alder cycloaddition. The resulting 7-phenyl-1,6-diazabicyclo[4.3.0]nona-3,7-dien-9-one (4) was reductively cleaved with Raney-Ni in alcoholic KOH to afford the mono-cyclic lactam 6. This was selectively alkylated in high yields to the cyano derivative 7. Reduction of the nitrile group to the amine derivative 8 went smoothly by use of Adam's catalyst in the presence of acid. Intramolecular transamidation was then accomplished by acid catalysis with TsOH to furnish the 13-membered diazalactam 9. The synthesis of (+/-)-1 was completed by the selective acetylation of the more nucleophilic amino group.