N-α-methoxy-N-(4-pentenoyl)pyrrolidine | 131656-92-3

• 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: N-α-methoxy-N-(4-pentenoyl)pyrrolidine
• 英文别名: 2-methoxy-N-(4-pentenoyl)pyrrolidine；1-(2-methoxypyrrolidin-1-yl)pent-4-en-1-one
• CAS: 131656-92-3
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: PASWCMFADKSTJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-α-methoxy-N-(4-pentenoyl)pyrrolidine 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 1-aza-5-chloro-2-oxobicyclo<5.3.0>decane
  参考文献：
  名称：

  阳极酰胺氧化：关于六元环和七元环在胺上环化的基础研究

  摘要：

  已经研究了烯烃和炔属亲核试剂与用于将六元和七元环融合到胺上的基于电化学的环化程序的相容性。发现单取代的烯烃和乙炔都是将七元环环合到胺上的良好亲核试剂。二取代的烯烃和乙炔似乎是完成六元环在胺上环化的良好亲核试剂。此外，还研究了几种脯氨酸衍生物与环合程序的相容性。

  DOI：

  10.1016/s0040-4020(01)87048-4
• 作为产物：
  描述：

  4-戊烯酸 在 草酰氯 、 sodium carbonate 、 四乙基对甲苯磺酸铵 作用下， 以 乙腈 为溶剂， 生成 N-α-methoxy-N-(4-pentenoyl)pyrrolidine
  参考文献：
  名称：

  Anodic amide oxidations in the presence of electron-rich phenyl rings: evidence for an intramolecular electron-transfer mechanism

  摘要：

  The anodic oxidations of amides in the presence of mono-, di-, and trialkoxyphenyl rings were examined. Although literature reduction potentials suggest that these oxidations would lead to either selective aromatic ring oxidation or mixtures, the chemoselectivity of the reactions was found to be dependent on the substitution pattern of the phenyl ring. For example, the anodic oxidations of ((3-methoxyphenyl)acetyl)pyrrolidine, ((2-methoxyphenyl)acetyl)pyrrolidine, ((3-methoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine, and ((3,5-dimethoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine all led to selective methoxylation of the pyrrolidine ring. The anodic oxidations of ((4-methoxyphenyl)acetyl)pyrrolidine and ((3,4-methoxyphenyl)acetyl)pyrrolidine led to selective methoxylation of the benzylic carbon. Mechanistic studies indicate that both amide and aryl oxidation processes compete under the reaction conditions, but that intramolecular electron transfer leads to the selective formation of products. Evidence for this mechanism was obtained by examining the cyclic voltammogram of ((3-methoxyphenyl)-acetyl)pyrrolidine, competition studies, and the preparative electrolysis of ((4-methoxyphenyl)dimethyl-acetyl)pyrrolidine. The methoxylated amides were cyclized to form tricyclic amides using titanium tetrachloride.

  DOI：

  10.1021/jo00003a029

文献信息

• MOELLER, KEVIN D.;WANG, PO W.;TARAZI, SHARIF;MARZABADI, MOHAMMAD R.;WONG,+, J. ORG. CHEM., 56,(1991) N, C. 1058-1067
  作者：MOELLER, KEVIN D.、WANG, PO W.、TARAZI, SHARIF、MARZABADI, MOHAMMAD R.、WONG,+

  DOI：——

  日期：——