1-丁基哌啶-2,6-二酮 | 58366-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-丁基哌啶-2,6-二酮
• 英文名称: N-butyl glutarimide
• 英文别名: N-Butyl-glutarimid；1-Butylpiperidine-2,6-dione
• CAS: 58366-40-8
• 化学式: C₉H₁₅NO₂
• mdl: MFCD21339677
• 分子量: 169.224
• InChiKey: SIWGQTHOLRHYBR-UHFFFAOYSA-N

物化性质

• 沸点：
  75-76 °C(Press: 0.15 Torr)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-丁基哌啶-2,6-二酮 在 草酰氯 、 dirhodium tetrapivalamidate 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 、 mineral oil 为溶剂， 反应 30.5h， 生成 9-butyl-9-azabicyclo[4.2.1]nonane-2,8-dione
  参考文献：
  名称：

  General Approach to Nitrogen-Bridged Bicyclic Frameworks by Rh-Catalyzed Formal Carbenoid Insertion into an Amide C–N Bond

  摘要：

  Various nitrogen-bridged bicyclic skeletons are found in bioactive natural products and pharmaceuticals. The development of a new reaction to construct these molecular frameworks has attracted considerable attention in synthetic organic chemistry. We developed a novel synthetic method for obtaining a wide variety of nitrogen-bridged bicyclic compounds with a catalytic process, Rh-catalyzed formal carbenoid insertion into an amide C-N bond. Using 0.1-0.4 mol % Rh-2((NHCOBu)-Bu-t)(4) catalyst, various azabicydo[X.Y.Z]alkane derivatives were obtained in good to excellent yield, successfully demonstrating the broad substrate scope of the developed process. Experimental and computational studies to elucidate the reaction mechanism revealed that the formal insertion reaction of a carbenoid into an amide C-N bond proceeded via the formation of Rh-associated N-ylides, followed by an acyl group-selective Stevens [1,2]-shift through a concerted addition/elimination process on the sp(2)-hybridized carbon.

  DOI：

  10.1021/acs.joc.5b01954
• 作为产物：
  描述：

  戊二酰基二氯 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-丁基哌啶-2,6-二酮
  参考文献：
  名称：

  N-Cyanoimides: reactivity studies with amine nucleophiles

  摘要：

  N-Cyanoimides are useful precursors to N-alkyl or N-aryl imides. Treatment of aromatic N-cyanoimides such as N-cyanophthalimide (1) with primary amines provides N-substituted imides directly, while aliphatic N-cyanoimides afford diamide intermediates which can be converted to N-substituted imides upon heating.

  DOI：

  10.1016/s0040-4039(00)77702-1

文献信息

• Solvent-mediated One-pot Synthesis of Cyclic<i>N</i>-Substituted Imides
  作者：Sambhaji V. Patil、Keshao A. Mahale、Kirankumar S. Gosavi、Ganesh B. Deshmukh、Nilesh S. Patil

  DOI：10.1080/00304948.2013.798569

  日期：2013.7.4

  synthesized by elaboration of N-aryl maleimides.16–19 Evaluation of the available methods for the synthesis of N-substituted cyclic imides indicates that generally the amines are first reacted with the desired cyclic anhydride and the resulting amic acids are then cyclized to the corresponding imides using reagents such as Ac2O/NaOAc, Et3N/Ac2O, dimethyl sulfate/Na2CO3/tetrabutylammonium bromide,27 cyanuric

  从现成的试剂中开发通用、高效的有机化合物合成方法是有机合成中的挑战之一。N-取代的环状酰亚胺在生物学、1-6 药理学、7 合成化学、8-19 聚合物化学、20,21 和材料科学中有许多应用。22,23 几种除草剂、24 杀虫剂、24 和抗真菌剂 1 以及宿主还通过精心设计 N-芳基马来酰亚胺合成了许多具有生物活性的天然产物。 16-19 对合成 N-取代环状酰亚胺的可用方法的评估表明，通常胺类首先与所需的环状酸酐反应，然后生成酰胺然后使用诸如 Ac2O/NaOAc、Et3N/Ac2O、硫酸二甲酯/Na2CO3/四丁基溴化铵等试剂将酸环化为相应的酰亚胺，27 氰尿酰氯/Et3N、[Bmim] [PF6]、140°C29 等。30-35 然而，其中一些程序 i) 缺乏通用性和可扩展性，ii) 使用苛刻的反应条件和危险的非绿色试剂， iii) 涉及繁琐的后处理和昂贵的试剂，iv) 产率低，有时会导致
• Catalytic Asymmetric Alkylation Reactions for the Construction of Protected Ethylene-Amino and Propylene-Amino Motifs Attached to Quaternary Stereocentres
  作者：Thomas A. Moss、David M. Barber、Andrew F. Kyle、Darren J. Dixon

  DOI：10.1002/chem.201203825

  日期：2013.2.25

  An efficient catalytic and stereoselective method for the direct construction of protected ethylene‐amino and propylene‐amino scaffolds attached to quaternary stereocentres is reported. Preliminary investigations revealed a mild base catalysed nucleophilic ring opening of N‐sulfonyl aziridines using the commercially available phosphazene base 2‐tert‐butylimino‐2‐diethylamino‐1,3‐dimethyl‐perhydro‐1

  据报道，一种有效的催化和立体选择性方法可直接构建连接到季立体中心的受保护的乙烯-氨基和丙烯-氨基骨架。初步研究表明，使用市售的磷腈碱2-叔丁基亚氨基-2-二乙氨基-1,3-二甲基-过氢-1,3,2-二氮杂磷（BEMP）可以催化N-磺酰基氮丙啶的轻度碱催化亲核开环。可能并导致与多种次甲基碳酸进行高效烷基化反应。可以使该反应高度不对称（ee高达97％），通过采用相转移催化来控制立体感应。将烷基取代基并入氮丙啶亲电子试剂中，导致该方法具有极高的非对映选择性（高达30：1 dr）。使用N保护的环氨基磺酸盐作为亲电子试剂的进一步扩展成功实现了一系列亲核试剂（高达96％ee和45：1 dr）并允许一系列氮保护基团（氨基甲酸酯，磺酰基，膦酰基，苄基） ）并结合到烷基化加合物中。最后，在有用的杂环和带有天然产物结构成分的化合物的合成中证明了产物的实用性。
• A synthesis of succinimides and glutarimides from cyclic anhydrides
  作者：Tadashi Kometani、Tony Fitz、David S. Watt

  DOI：10.1016/s0040-4039(00)84137-4

  日期：1986.1

  The transformation of cyclic anhydrides to their corresponding imides involves a mild three-step sequence: (1) reaction with a primary amine, (2) conversion of the intermediate monoamide to an N-hydroxysuccinimidyl ester using N,N′-disuccinimidyl oxalate (DSO), and (3) cyclization by heating the NHS ester in trichloroethylene in the presence of 4-(dimethylamino)pyridine.

  环状酸酐向其相应的酰亚胺的转化涉及温和的三个步骤：（1）与伯胺反应，（2）使用N，N'-二琥珀酰亚胺草酸酯（DSO）将中间体单酰胺转化为N-羟基琥珀酰亚胺酯），和（3）在4-氯代二甲基氨基吡啶存在下，在三氯乙烯中加热NHS酯来环化。
• NANOCOMPOSITE AND DISPERSION COMPRISING THE SAME
  申请人：Morishita Takuya

  公开号：US20120053288A1

  公开（公告）日：2012-03-01

  A nanocomposite comprises a nanostructure, and a copolymer adsorbed to the nanostructure and containing at least one ionic monomer unit and a different monomer unit from the ionic monomer unit; the ionic monomer unit selected from the group consisting of a zwitterionic monomer unit and a cationic monomer unit which are represented by the following formula (1): (in the formula (1), R 1 , R 2 , and R 3 each independently represent any one of a hydrogen atom and a monovalent organic group having 1 to 20 carbon atoms, Y 1 represents any one of a carbonyl group and an arylene group, Y 2 represents any one of —O— and —NH—, n is 0 or 1, R 4 represents a divalent organic group having 1 to 20 carbon atoms, and X represents any one of a zwitterionic group and a cationic group).

  一种纳米复合材料包括纳米结构和吸附在纳米结构上的共聚物，该共聚物包含至少一个离子单体单元和一个不同于离子单体单元的单体单元；所述离子单体单元选自以下公式（1）表示的带电单体单元组中的具有两性离子单体单元和阳离子单体单元：（在公式（1）中，R1、R2和R3各自独立地表示氢原子和具有1到20个碳原子的一价有机基团，Y1表示羰基基团和芳基基团中的任意一种，Y2表示-O-和-NH-中的任意一种，n为0或1，R4表示具有1到20个碳原子的二价有机基团，X表示具有两性离子基团和阳离子基团中的任意一种）。
• Unsaturated Lactams: New Inputs for Povarov-Type Multicomponent Reactions
  作者：Esther Vicente-García、Federica Catti、Rosario Ramón、Rodolfo Lavilla

  DOI：10.1021/ol902913j

  日期：2010.2.19

  Unsaturated lactams with endo- or exocyclic C-C double bonds constitute a set of reactive inputs that serve as the electron-rich olefin component in Povarov reactions. These substrates afford the multicomponent adducts in convenient yields and offer a wide range of structural diversity. Postcondensation transformations allow direct access to a variety of lactam-fused and amide-substituted quinoline derivatives.