N-benzyloxycarbonyl-2-(2-oxoheptyl)pyrrolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyloxycarbonyl-2-(2-oxoheptyl)pyrrolidine
• 英文别名: Benzyl 2-(2-oxoheptyl)pyrrolidine-1-carboxylate
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: BLVDHDCTHKABAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氨基丁醛缩二乙醇 、 N-benzyloxycarbonyl-2-(2-oxoheptyl)pyrrolidine 在 sodium tetrahydroborate 、 3 A molecular sieve 、 Amberlyst A-15 作用下， 生成 benzyl 2-[2-(4,4-diethoxybutylamino)heptyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Short syntheses of (±)-tetraponerines-5 and -6. the structures of tetraponerines-1 and -2, and a revision of the structures of (+)-tetraponerines-5 and -6

  摘要：

  The structures and absolute configurations of (+)-tetraponerines-5 and -6 [(+)-T-5 and (+)-T-6], from the poison gland of the ant Tetraponera sp., were reassigned as 7 and 8, respectively, on the basis of extensive two-dimensional NMR and CD studies. These results led to structure proposals 9 for T-1 and 10 for T-2, the two minor alkaloids of the venom. The structures and relative configurations of T-5 and T-6 were subsequently confirmed by short stereoselective syntheses.

  DOI：

  10.1016/0040-4020(95)00667-w
• 作为产物：
  描述：

  氯甲酸苄酯 、 1-Pyrrolidin-2-yl-heptan-2-one 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以86%的产率得到N-benzyloxycarbonyl-2-(2-oxoheptyl)pyrrolidine
  参考文献：
  名称：

  Short syntheses of (±)-tetraponerines-5 and -6. the structures of tetraponerines-1 and -2, and a revision of the structures of (+)-tetraponerines-5 and -6

  摘要：

  The structures and absolute configurations of (+)-tetraponerines-5 and -6 [(+)-T-5 and (+)-T-6], from the poison gland of the ant Tetraponera sp., were reassigned as 7 and 8, respectively, on the basis of extensive two-dimensional NMR and CD studies. These results led to structure proposals 9 for T-1 and 10 for T-2, the two minor alkaloids of the venom. The structures and relative configurations of T-5 and T-6 were subsequently confirmed by short stereoselective syntheses.

  DOI：

  10.1016/0040-4020(95)00667-w

文献信息

• Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives
  作者：Santos Fustero、Diego Jiménez、María Sánchez-Roselló、Carlos del Pozo

  DOI：10.1021/ja0709829

  日期：2007.5.1

  Hoveyda-Grubbs catalyst in combination with BF3 center dot OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of beta-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched alpha-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.
• Short syntheses of (±)-tetraponerines-5 and -6. the structures of tetraponerines-1 and -2, and a revision of the structures of (+)-tetraponerines-5 and -6
  作者：Christine Devijver、Pascale Macours、Jean-Claude Braekman、Désiré Daloze、Jacques M. Pasteels

  DOI：10.1016/0040-4020(95)00667-w

  日期：1995.10

  The structures and absolute configurations of (+)-tetraponerines-5 and -6 [(+)-T-5 and (+)-T-6], from the poison gland of the ant Tetraponera sp., were reassigned as 7 and 8, respectively, on the basis of extensive two-dimensional NMR and CD studies. These results led to structure proposals 9 for T-1 and 10 for T-2, the two minor alkaloids of the venom. The structures and relative configurations of T-5 and T-6 were subsequently confirmed by short stereoselective syntheses.