rac-1-{[(1S,9S,10S)-12-acetyl-8-methyl-8,12-diazatricyclo[7.3.1.0(2,7)]trideca-2(7),3,5-trien-12-yl]methyl}pyrrolidine-2,5-dione

• 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: rac-1-{[(1S,9S,10S)-12-acetyl-8-methyl-8,12-diazatricyclo[7.3.1.0(2,7)]trideca-2(7),3,5-trien-12-yl]methyl}pyrrolidine-2,5-dione
• 英文别名: (1S,9Z,12R,16S)-N-[3,5-bis(trifluoromethyl)phenyl]-15-methyl-14-oxa-8-thia-10,15-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-2,4,6-trien-9-imine；1-[[(1S,9S,10S)-12-acetyl-8-methyl-8,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-trien-10-yl]methyl]pyrrolidine-2,5-dione
• 化学式: C₁₉H₂₃N₃O₃
• 分子量: 341.41
• InChiKey: ZVFWVXJUVXJBTO-JQFCIGGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-((2SR,4SR,5RS)-2-(2-bromophenyl)-5-(hydroxymethyl)-4-(methylamino)piperidin-1-yl)ethanone 在 偶氮二甲酸二异丙酯 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.0h， 生成 rac-1-{[(1S,9S,10S)-12-acetyl-8-methyl-8,12-diazatricyclo[7.3.1.0(2,7)]trideca-2(7),3,5-trien-12-yl]methyl}pyrrolidine-2,5-dione
  参考文献：
  名称：

  Multicomponent Assembly and Diversification of Novel Heterocyclic Scaffolds Derived from 2-Arylpiperidines

  摘要：

  A collection of structurally diverse, polyheterocyclic scaffolds comprising a 2-arylpiperidine subunit were synthesized using a Mannich-type multicomponent assembly process, followed by appropriately sequenced ring-forming reactions. An Improved procedure for removal of N-4-pentenoyl groups was developed; one-pot sequences for tandem urea/thiourea formation and cyclization and tandem enolate arylation/alkylation were discovered. A novel entry to bridged tetrahydroquinoline scaffolds exploiting A(1,3) strain was also invented. Derivatization of several scaffolds was achieved by cross-coupling and N-functionalization.

  DOI：

  10.1021/ol201010s

文献信息

• Multicomponent Assembly and Diversification of Novel Heterocyclic Scaffolds Derived from 2-Arylpiperidines
  作者：Simon Hardy、Stephen F. Martin

  DOI：10.1021/ol201010s

  日期：2011.6.17

  A collection of structurally diverse, polyheterocyclic scaffolds comprising a 2-arylpiperidine subunit were synthesized using a Mannich-type multicomponent assembly process, followed by appropriately sequenced ring-forming reactions. An Improved procedure for removal of N-4-pentenoyl groups was developed; one-pot sequences for tandem urea/thiourea formation and cyclization and tandem enolate arylation/alkylation were discovered. A novel entry to bridged tetrahydroquinoline scaffolds exploiting A(1,3) strain was also invented. Derivatization of several scaffolds was achieved by cross-coupling and N-functionalization.