tert-butyl 2-(2-oxo-4-phenylbut-3-ynyl)pyrrolidine-1-carboxylate | 905717-08-0

• 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-oxo-4-phenylbut-3-ynyl)pyrrolidine-1-carboxylate
• 英文别名: Tert-butyl 2-(2-oxo-4-phenylbut-3-ynyl)pyrrolidine-1-carboxylate
• CAS: 905717-08-0
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: ZWUCDJVOWAYNIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-oxo-4-phenylbut-3-ynyl)pyrrolidine-1-carboxylate 在 盐酸 、 甲醇 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以89%的产率得到5-phenyl-2,3,8,8a-tetrahydroindolizin-7(1H)-one
  参考文献：
  名称：

  Amino Acid-Derived Enaminones:  A Study in Ring Formation Providing Valuable Asymmetric Synthons

  摘要：

  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.

  DOI：

  10.1021/ja0609046
• 作为产物：
  描述：

  1-Boc-2-吡咯烷乙酸 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 tert-butyl 2-(2-oxo-4-phenylbut-3-ynyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Amino Acid-Derived Enaminones:  A Study in Ring Formation Providing Valuable Asymmetric Synthons

  摘要：

  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.

  DOI：

  10.1021/ja0609046

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.