1-(2-allyl-pyrrolidine-1-yl)ethanone | 918631-41-1

• 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: 1-(2-allyl-pyrrolidine-1-yl)ethanone
• 英文别名: 1-acetyl-2-allylpyrrolidine；1-(2-allylpyrrolidin-1-yl)ethan-1-one；1-(2-allyl-pyrrolidin-1-yl)ethanone；1-[2-(Prop-2-en-1-yl)pyrrolidin-1-yl]ethan-1-one；1-(2-prop-2-enylpyrrolidin-1-yl)ethanone
• CAS: 918631-41-1
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: WQSVRNLKGGQOPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-乙酰基吡咯烷 在 四氯化钛 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 1-(2-allyl-pyrrolidine-1-yl)ethanone
  参考文献：
  名称：

  双(2,2,2-三氯乙基)偶氮二甲酸酯对胺衍生物的α-氧化及其产物作为亚胺离子等价物的应用

  摘要：

  Alpha-oxidation of amine derivatives by azodicarboxylate was examined. Among several azodicarboxylate esters and amides tested, bis(2,2,2-trichloroethyl) azodicarboxylate, that has highly electrophilic 2,2,2-trichloroethoxycarbonyl functional groups, was found to have excellent oxidation reactivity. Acylated or carbamoylated amines were suitable substrates for this reaction condition. Tertially amines could react in the same manner, but spontaneous elimination of hydrazinyl group occurred to give dimerized products. The reaction products were found to react with nucleophiles in the presence of Lewis or Bronsted acid catalyst. This strongly suggests that the reaction products, alpha-hydrazinated amine derivatives, might serve as carbonyl group equivalents, very useful intermediates in synthetic organic chemistry.

  DOI：

  10.3987/com-16-s(s)70

文献信息

• Palladium(II)-Catalyzed Intramolecular Hydroamination of 1,3-Dienes to Give Homoallylic Amines
  作者：Justin M. Pierson、Erica L. Ingalls、Richard D. Vo、Forrest E. Michael

  DOI：10.1002/anie.201305766

  日期：2013.12.9

  A pincer for high selectivity: A mild palladium‐catalyzed hydroamination of protected amino‐1,3‐dienes is possible. This highly regioselective reaction employs a tridentate PNP pincer ligand and leads to cyclic and homoallylic protected amines in high yields. Substrates with a wide array of amine protecting groups and diene substitution patterns were cyclized to form five‐ and six‐membered heterocycles

  高选择性的选择：受保护的1，3-二烯氨基的轻度钯催化加氢胺化是可能的。这种高度区域选择性的反应使用三齿PNP钳形配体，并以高收率得到环状和均烯丙基保护的胺。具有多种胺保护基和二烯取代模式的底物被环化以形成五元和六元杂环。PG ＝保护基。
• Development of an anodic substitution reaction system using acoustic emulsification
  作者：Ryosuke Asami、Toshio Fuchigami、Mahito Atobe

  DOI：10.1039/b713859h

  日期：——

  The anodic substitution reaction proceeded smoothly without affecting the oxidation of the nucleophile in a one-step electrochemical operation using acoustic emulsification.

  在利用声波乳化技术进行的一步电化学操作中，阳极取代反应顺利进行，不会影响亲核物的氧化。
• A new approach to anodic substitution reaction using acoustic emulsification
  作者：Ryosuke Asami、Toshio Fuchigami、Mahito Atobe

  DOI：10.1039/b802961j

  日期：——

  We have developed a novel electrolytic system for anodic substitution reactions using acoustic emulsification. This new system involves the generation of a carbocation by anodic oxidation of a substrate, and then its reaction with a nucleophile droplet formed by ultrasonication. In this system, even if the oxidation potential of the nucleophile is lower than that of the substrate, the substrate was predominantly oxidized to give the corresponding cation intermediate because the nucleophile phase, which was insoluble in the electrolytic medium, was electro-inactive. In addition, the overoxidation of the desired products was considerably suppressed by the extraction of products from the electrolyte solution into the nucleophile phase. As a result, the anodic substitution reaction of several carbamates with allyltrimethylsilane was carried out to provide the corresponding products in good to moderate yields.

  我们开发了一种新型电解系统，用于利用声乳化技术进行阳极置换反应。这种新系统通过阳极氧化底物产生碳阳离子，然后使其与超声波形成的亲核液滴发生反应。在该系统中，即使亲核物质的氧化电位低于底物的氧化电位，底物也会优先氧化，生成相应的阳离子中间体，因为不溶于电解介质的亲核相不具有电活性。此外，通过将产物从电解质溶液中萃取到亲核相中，可以显著抑制所需产物的过度氧化。因此，几种氨基甲酸酯与烯丙基三甲基硅烷的阳极置换反应能够以良好至中等产率生成相应的产物。
• Development of Method for the Efficient α-Oxidation of tert-Alkylamines Using bis(2,2,2-Trichloroethyl) Azodicarboxylate
  作者：Takumichi Sugihara、Shinobu Honzawa、Mitsuaki Uchida

  DOI：10.3987/com-13-s(s)108

  日期：——

  An efficient alpha-oxidation of amines can be accomplished using bis(2,2,2-trichloroethyl) azodicarboxylate, which is more electrophilic than diethyl azodicarboxylate, often used in synthetic chemistry. N-Acetyl and N-tert-butoxycarbonylamines are good substrates for this alpha-oxidation, and in the case of N-phenylpyrrolidine an interesting dimerization reaction is followed by alpha-oxidation. The alpha-oxidation product can be transformed in the presence of nucleophiles and a Lewis acid to alpha-modified amines, presumably via an iminium intermediate.
• Alpha-Oxidation of Amine Derivatives by bis(2,2,2-Trichloroethyl) Azodicarboxylate and Application of Its Products as Iminium Ion Equivalents
  作者：Shinobu Honzawa、Takumichi Sugihara、Mitsuaki Uchida、Takuya Tashiro

  DOI：10.3987/com-16-s(s)70

  日期：——

  Alpha-oxidation of amine derivatives by azodicarboxylate was examined. Among several azodicarboxylate esters and amides tested, bis(2,2,2-trichloroethyl) azodicarboxylate, that has highly electrophilic 2,2,2-trichloroethoxycarbonyl functional groups, was found to have excellent oxidation reactivity. Acylated or carbamoylated amines were suitable substrates for this reaction condition. Tertially amines could react in the same manner, but spontaneous elimination of hydrazinyl group occurred to give dimerized products. The reaction products were found to react with nucleophiles in the presence of Lewis or Bronsted acid catalyst. This strongly suggests that the reaction products, alpha-hydrazinated amine derivatives, might serve as carbonyl group equivalents, very useful intermediates in synthetic organic chemistry.