tert-butyl 2-(2-oxobut-3-yn-1-yl)pyrrolidine-1-carboxylate | 905717-01-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: tert-butyl 2-(2-oxobut-3-yn-1-yl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl 2-(2-oxobut-3-ynyl)pyrrolidine-1-carboxylate
• CAS: 905717-01-3
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: JNSSQWLAEJDPPH-UHFFFAOYSA-N

物化性质

• 沸点：
  341.2±15.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  tert-butyl 2-(2-oxobut-3-yn-1-yl)pyrrolidine-1-carboxylate 在 甲醇 、 甲酸 、 叔丁基锂 、 L-Selectride 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 16.67h， 生成 7-(2',4,5-trimethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine
  参考文献：
  名称：

  Synthesis of Tylocrebrine and Related Phenanthroindolizidines by VOF₃-Mediated Oxidative Aryl-Alkene Coupling

  摘要：

  A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

  DOI：

  10.1021/ol1023954
• 作为产物：
  描述：

  N-BOC-吡咯-2-乙酸乙酯 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 tert-butyl 2-(2-oxobut-3-yn-1-yl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Tylocrebrine and Related Phenanthroindolizidines by VOF₃-Mediated Oxidative Aryl-Alkene Coupling

  摘要：

  A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

  DOI：

  10.1021/ol1023954

文献信息

• Amino Acid-Derived Enaminones:  A Study in Ring Formation Providing Valuable Asymmetric Synthons
  作者：Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/ja0609046

  日期：2006.7.1

  A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.