(2S,4S)-tert-butyl 4-hydroxy-2-(2-oxobut-3-ynyl)pyrrolidine-1-carboxylate | 905717-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,4S)-tert-butyl 4-hydroxy-2-(2-oxobut-3-ynyl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S,4S)-4-hydroxy-2-(2-oxobut-3-ynyl)pyrrolidine-1-carboxylate
• CAS: 905717-29-5
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: LWHARZQTKOMJRB-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 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：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S)-tert-butyl 4-hydroxy-2-(2-oxobut-3-ynyl)pyrrolidine-1-carboxylate 在 碘代三甲硅烷 、 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以70%的产率得到2-hydroxy-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：

  2-((2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidin-2-yl)acetic acid 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 (2S,4S)-tert-butyl 4-hydroxy-2-(2-oxobut-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

• Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism
  作者：Micah J. Niphakis、Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/jo100907u

  日期：2010.10.15

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction 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 die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).