N-丁基吡咯烷-1-甲酰胺 | 1461-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: N-丁基吡咯烷-1-甲酰胺
• 英文名称: N-butylpyrrolidine-1-carboxamide
• 英文别名: pyrrolidine-1-carboxylic acid butylamide；N'-butylpyrrolidine-N-carboxamide；1-Pyrrolidinecarboxamide, N-butyl-
• CAS: 1461-78-5
• 化学式: C₉H₁₈N₂O
• mdl: MFCD06088063
• 分子量: 170.255
• InChiKey: UORJYVGJSYXIOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-amino-3-(benzylsulfanyl)-N-butyl-1H-[1,2,4]triazole-1-carboxamide 在 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-丁基吡咯烷-1-甲酰胺
  参考文献：
  名称：

  Triazolo [1,5 - a ] triazin-7-one衍生物和高度官能化的[1,2,4]三唑的合成

  摘要：

  介绍了新型三唑并[1,5- a ]三嗪-7-ones的合成。从3-氨基-5-硫烷基-1,2,4-三唑开始，合成序列包括用苄基溴进行烷基化，与氯甲酸对硝基苯酯反应，然后用伯胺处理，并与二乙氧基甲基乙酸酯缩合。用3-氯过苯甲酸最终氧化硫醚部分，得到总体良好的2-（苄基磺酰基）[1,2,4]三唑[1,5- a ] [1,3,5]三嗪-7- a 5a和5b产量。5a和5b的治疗与仲胺的混合物通过意外的三嗪酮开环提供了高度官能化的[1,2,4]三唑。提出了这种转变的机制。

  DOI：

  10.1002/hlca.200390261

文献信息

• Schmidt Reaction of ω-Azido Valeryl Chlorides Followed by Intermolecular Trapping of the Rearrangement Ions: Synthesis of Assoanine and Related Pyrrolophenanthridine Alkaloids
  作者：Shao-Lei Ding、Yang Ji、Yan Su、Rui Li、Peiming Gu

  DOI：10.1021/acs.joc.8b03018

  日期：2019.2.15

  The Schmidt reaction of ω-azido valeryl chlorides in the presence of an additional nucleophile was explored. The arenes, alcohols, and amines were demonstrated as the intermolecular trapping reagents for isocyanate ion and N-acyliminium ion from the Schmidt rearrangement, affording the corresponding products with moderate to excellent yields. Two 2-oxoindoles from the reaction were successfully converted

  探索了在存在其他亲核试剂的情况下ω-叠氮基戊酰氯的Schmidt反应。证明了芳烃，醇和胺是施密特重排中异氰酸酯离子和N-酰基亚胺离子的分子间捕获剂，从而以中等至极好的收率提供了相应的产物。来自该反应的两个2-氧代吲哚被成功地转化为四种天然生物碱，即，伴生素，脱水赖氨酸，氧代伴嘌呤和脱水赖皮酮。
• Synthesis of urea derivatives from amines and CO2 in the absence of catalyst and solvent
  作者：Chaoyong Wu、Haiyang Cheng、Ruixia Liu、Qiang Wang、Yufen Hao、Yancun Yu、Fengyu Zhao

  DOI：10.1039/c0gc00059k

  日期：——

  Urea derivatives are obtained in mild to good yield from the reactions of primary aliphatic amines with CO2 in the absence of any catalysts, organic solvents or other additives. To optimize reaction conditions, experimental variables including temperature, pressure, the concentration of amine, reaction time etc. were studied. Satisfactory yields were obtained at the optimized conditions that are comparable

  尿素 从 脂肪族伯胺用CO 2在没有任何催化剂， 有机的 溶剂或其他添加剂。为了优化反应条件，研究了温度，压力，胺浓度，反应时间等实验变量。在优化的条件下获得了令人满意的产量，与存在下的可比性相当。催化剂 和 溶剂。对反应机理的初步研究表明，烷基氨基甲酸烷基铵迅速形成了中间体，然后通过分子内脱水形成了最终产物。
• Process for the N-alkylation or ureas
  申请人：Chemie Linz Gesellschaft m.b.H.

  公开号：US05124451A1

  公开（公告）日：1992-06-23

  Process for the N-alkylation of ureas by reacting a urea with an alkylating agent in the presence of a solid base and a phase transfer catalyst in a diluent.

  尿素的N-烷基化过程是通过在稀释剂中，在固体碱和相转移催化剂的存在下，将尿素与烷基化剂反应实现的。
• Conversion of carbonimidodithioates into unsymmetrical Di- and Tri- substituted ureas including urea dipeptides
  作者：Mariappan Anbazhagan、Abdul Rakeeb A.S. Deshmukh、Srinivasachari Rajappa

  DOI：10.1016/s0040-4039(98)00561-9

  日期：1998.5

  Selective hydrolysis of carbonimidodithioates (3) leads to the thiocarbamates (4), which can be easily transformed to the unsymmetrical ureas (5) by treatment with the appropriate amines. This constitutes a synthesis of ureas without the use of phosgene or carbon monoxide.

  碳亚氨基二硫代碳酸酯（3）的选择性水解会生成硫代氨基甲酸酯（4），通过用适当的胺处理，硫代氨基甲酸酯（4）可以轻松转化为不对称脲（5）。这构成了不使用光气或一氧化碳的脲的合成。
• The synthesis of N-substituted ureas I: The N-alkylation of ureas
  作者：Kurt A. Hackl、Heinz Falk

  DOI：10.1007/bf00816855

  日期：——

  Urea and N-alkylureas are N'-alkylated in low yields using aprotic dipolar solvents, like dimethylsulfoxide, solid potassium hydroxide, and alkyl halides. Phase transfer catalysis with tetrabutylammonium chloride in refluxing toluene results in high yield regioselective N'-alkylation of N-alkylureas by means of alkyl halides, tosylates, mesylates, and sulfates as alkylating agents and alkali hydroxide as the base - however, N-arylureas are not alkylated under these conditions. Kinetic studies point to a S(N)2 type reaction which obeys the Kornblum rule.