(2SR,4RS)-tert-butyl 4-(benzyloxy)-2-(2-oxopent-3-ynyl)pyrrolidine-1-carboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2SR,4RS)-tert-butyl 4-(benzyloxy)-2-(2-oxopent-3-ynyl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S,4R)-2-(2-oxopent-3-ynyl)-4-phenylmethoxypyrrolidine-1-carboxylate
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: GTGGMQQXOJXPJS-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2SR,4RS)-tert-butyl 4-(benzyloxy)-2-(2-oxopent-3-ynyl)pyrrolidine-1-carboxylate 在 甲酸 、 sodium iodide 作用下， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism

  摘要：

  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).

  DOI：

  10.1021/jo100907u
• 作为产物：
  描述：

  (2SR,4RS)-tert-butyl 4-(benzyloxy)-2-(2-(methoxy(methyl)amino)-2-oxoethyl)pyrrolidine-1-carboxylate 、 1-丙炔溴化镁 以 四氢呋喃 为溶剂， 以90%的产率得到(2SR,4RS)-tert-butyl 4-(benzyloxy)-2-(2-oxopent-3-ynyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism

  摘要：

  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).

  DOI：

  10.1021/jo100907u

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).