1-(3-aminopropyl)-4-phenyl-1,5-diazacyclononan-2-one | 141991-06-2

• 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: 1-(3-aminopropyl)-4-phenyl-1,5-diazacyclononan-2-one
• 英文别名: 3-phenyl-9-(3'-aminopropyl)-4-azaoctanelactam；1-(3-Aminopropyl)-4-phenyl-1,5-diazonan-2-one
• CAS: 141991-06-2
• 化学式: C₁₆H₂₅N₃O
• 分子量: 275.394
• InChiKey: DCKNCRJTGNZPFE-UHFFFAOYSA-N

物化性质

• 沸点：
  472.8±45.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-aminopropyl)-4-phenyl-1,5-diazacyclononan-2-one 在 对甲苯磺酸 作用下， 以 xylene 为溶剂， 反应 3.0h， 以63%的产率得到2-phenyl-1,5,9-triazacyclotridecan-4-one
  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
• 作为产物：
  描述：

  Beta-溴苯丙酸 在 盐酸 、 1,4-Dimethyl-1,2-dihydro-pyridin 、 sodium hydride 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.5h， 生成 1-(3-aminopropyl)-4-phenyl-1,5-diazacyclononan-2-one
  参考文献：
  名称：

  β-内酰胺作为大环精胺和亚精胺生物碱合成的基础

  摘要：

  大环亚精胺生物碱（±）-celacinnine（1）和（±）-二氢茶碱（2）以及相关的亚精胺生物碱（±）-verbascenine（3）的合成是通过较小内酰胺环的连续环扩展来完成的。使用了三种扩环方法：（1）N-（氨基烷基）内酰胺的转酰胺基化，（2）β-内酰胺-内酰胺醚缩合，然后用NaBH 3 CN / AcOH还原双环4-氧代四氢嘧啶产物和（3）形成双环酰基肼，然后用Na / NH 3裂解N–N键。每个合成均以4-苯基氮杂环丁烷-2-酮中间体的扩环为特征，该中间体会发生酰胺基扩环或内酰胺醚缩合反应。

  DOI：

  10.1016/s0040-4020(02)00731-7

文献信息

• Wasserman, Harry H.; Robinson, Ralph P., Heterocycles, 1984, vol. 21, # 1, p. 279 - 288
  作者：Wasserman, Harry H.、Robinson, Ralph P.

  DOI：——

  日期：——
• Begley, Michael J.; Crombie, Leslie; Haigh, David, Journal of the Chemical Society. Perkin transactions I, 1993, # 17, p. 2027 - 2046
  作者：Begley, Michael J.、Crombie, Leslie、Haigh, David、Jones, Raymond C. F.、Osborne, Steven、Webster, Richard A. B.

  DOI：——

  日期：——
• β-Lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids
  作者：Harry H Wasserman、Haruo Matsuyama、Ralph P Robinson

  DOI：10.1016/s0040-4020(02)00731-7

  日期：2002.8

  Syntheses of the macrocyclic spermidine alkaloids (±)-celacinnine (1) and (±)-dihydroperiphylline (2) as well as the related spermine alkaloid (±)-verbascenine (3) were accomplished by means of sequential ring expansions of smaller lactam rings. Three ring expansion methods were employed: (1) transamidation of N-(aminoalkyl)lactams, (2) β-lactam-lactim ether condensation followed by reductive cleavage

  大环亚精胺生物碱（±）-celacinnine（1）和（±）-二氢茶碱（2）以及相关的亚精胺生物碱（±）-verbascenine（3）的合成是通过较小内酰胺环的连续环扩展来完成的。使用了三种扩环方法：（1）N-（氨基烷基）内酰胺的转酰胺基化，（2）β-内酰胺-内酰胺醚缩合，然后用NaBH 3 CN / AcOH还原双环4-氧代四氢嘧啶产物和（3）形成双环酰基肼，然后用Na / NH 3裂解N–N键。每个合成均以4-苯基氮杂环丁烷-2-酮中间体的扩环为特征，该中间体会发生酰胺基扩环或内酰胺醚缩合反应。
• 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.