1-(1-苯基乙基)吡咯烷-2,5-二酮 | 86841-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(1-苯基乙基)吡咯烷-2,5-二酮
• 英文名称: 1-(1-phenylethyl)-2,5-pyrrolidinedione
• 英文别名: 1-benzylpyrrolidine-2,5-dione；N-(1-phenylethyl)succinimide；1-(1-Phenylethyl)pyrrolidine-2,5-dione
• CAS: 86841-96-5
• 化学式: C₁₂H₁₃NO₂
• mdl: MFCD24388927
• 分子量: 203.241
• InChiKey: YTUMRJVSFMABFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 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-(1-苯基乙基)吡咯烷-2,5-二酮 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 5-(1H-indol-3-yl)-1-(1-phenylethyl)pyrrolidin-2-one
  参考文献：
  名称：

  Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2-ones from available reagents

  摘要：

  The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones.

  DOI：

  10.1007/s10593-011-0655-x
• 作为产物：
  描述：

  N-(1-phenylethyl)-succinamic acid 在 溶剂黄146 、 三乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 以56%的产率得到1-(1-苯基乙基)吡咯烷-2,5-二酮
  参考文献：
  名称：

  Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2-ones from available reagents

  摘要：

  The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones.

  DOI：

  10.1007/s10593-011-0655-x

文献信息

• [EN] PROCESS OF FORMING A CYCLIC IMIDE<br/>[FR] PROCÉDÉ DE FORMATION D'UN IMIDE CYCLIQUE
  申请人：UNIV NANYANG TECH

  公开号：WO2012002913A1

  公开（公告）日：2012-01-05

  A process is provided for the synthesis of a cyclic imide. A primary amine and a diol compound are contacted in the presence of a Ruthenium (II) complex. The Ruthenium (II) catalyst includes at least one of an alicyclic ligand, an aromatic ligand, an arylalicyclic ligand, an arylaliphatic ligand and a phosphine ligand.

  提供一种合成环戊二酰亚胺的过程。在钌（II）配合物存在的情况下，将一种初级胺和一种二醇化合物接触。钌（II）催化剂包括至少一种脂环配体、芳香配体、芳基脂环配体、芳基脂肪配体和膦配体。
• [EN] MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS<br/>[FR] COMPLEXES À BASE DE MANGANÈSE ET LEURS UTILISATIONS SERVANT À UNE CATALYSE HOMOGÈNE
  申请人：YEDA RES & DEV

  公开号：WO2017137984A1

  公开（公告）日：2017-08-17

  The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C-C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di- lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.

  本发明涉及新型锰配合物及其用途，包括但不限于在以下领域进行均相催化：（1）通过醇和胺的脱氢偶联制备亚胺；（2）使用腈作为迈克尔供体进行迈克尔加成反应中的C-C偶联；（3）将醇脱氢偶联以得到酯和氢气；（4）将酯加氢以形成醇（包括环酯（内酯）或环二酯（二内酯）或聚酯的加氢）；（5）将酰胺（包括环二肽、内酰胺、二酰胺、多肽和聚酰胺）加氢以得到醇和胺（或二胺）；（6）将有机碳酸酯（包括聚碳酸酯）加氢以得到醇或将氨基甲酸酯（包括聚氨基甲酸酯）或脲衍生物加氢以得到醇和胺；（7）将二级醇脱氢以得到酮；（8）酯的酰胺化（即从酯和胺合成酰胺）；（9）使用酯对醇进行酰化；（10）将醇与水和碱偶联以形成羧酸；以及（11）通过氨基醇与水和碱的偶联制备氨基酸或其盐。（12）通过醇和胺的脱氢偶联制备酰胺（包括甲酰胺、环二肽、二酰胺、内酰胺、多肽和聚酰胺）；（13）从二醇制备酰亚胺。
• Synthesis of Cyclic Imides from Simple Diols
  作者：Jian Zhang、Muthaiah Senthilkumar、Subhash Chandra Ghosh、Soon Hyeok Hong

  DOI：10.1002/anie.201002136

  日期：2010.8.23

  There′s something imide so strong: Cyclic imides were synthesized from simple diols with primary amines in a single step using an in‐situ‐generated ruthenium catalytic system. The atom‐economical and operatively simple syntheses of succinimides, phthalimides, and glutarimides, which are important building blocks in natural products and drugs, was also demonstrated.

  有一个如此强大的酰亚胺：环酰亚胺是使用原位生成的钌催化系统，由简单的二醇与伯胺一步合成而成的。还展示了琥珀酰亚胺，邻苯二甲酰亚胺和戊二酰亚胺的原子经济实用的合成方法，它们是天然产物和药物的重要组成部分。
• Versatile and Sustainable Synthesis of Cyclic Imides from Dicarboxylic Acids and Amines by Nb₂O₅as a Base-Tolerant Heterogeneous Lewis Acid Catalyst
  作者：Md. Ayub Ali、S. M. A. Hakim Siddiki、Kenichi Kon、Junya Hasegawa、Ken-ichi Shimizu

  DOI：10.1002/chem.201404538

  日期：2014.10.27

  Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom‐efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2O5 as a reusable and base‐tolerant heterogeneous Lewis acid catalyst. The method is effective for

  二羧酸和胺的催化缩合反应没有过量的活化剂是最高效，最空前的环状酰亚胺合成方法。在这里，我们介绍了第一种通用催化方法，该方法在作为可重用和耐碱多相路易斯酸催化剂的商业Nb 2 O 5的存在下选择性而有效地进行。该方法可有效地从二羧酸或酸酐与胺，羟胺或氨直接合成药学上或工业上重要的环状酰亚胺，例如苯甲酰亚胺，N-羟基邻苯二甲酰亚胺（NHPI）和未取代的环状酰亚胺。
• A NOVEL METHOD FOR THE ONE-STEP SYNTHESIS OF<i>N</i>-ALKYL IMIDES BY THE USE OF 1,1′-DIMETHYLSTANNOCENE
  作者：Teruaki Mukaiyama、Junji Ichikawa、Makoto Toba、Masatoshi Asami

  DOI：10.1246/cl.1983.879

  日期：1983.6.5

  Various N-alkyl imides are easily prepared in good yields under nearly neutral conditions from equimolar amounts of cyclic acid anhydrides and primary amines by the use of 1,1′-dimethylstannocene.

  使用 1,1′-二甲基锡烯，可以在接近中性的条件下，用等摩尔量的环酸酐和伯胺轻松制备出各种 N-烷基亚胺，而且产率很高。