1-[(4-fluorophenyl)methyl]-2,6-piperidinedione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-[(4-fluorophenyl)methyl]-2,6-piperidinedione
• 英文别名: 1-(4-Fluorobenzyl)piperidine-2,6-dione；1-[(4-fluorophenyl)methyl]piperidine-2,6-dione
• 化学式: C₁₂H₁₂FNO₂
• mdl: MFCD09880291
• 分子量: 221.231
• InChiKey: RTROAVKNHOHZBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 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：
  3

反应信息

• 作为产物：
  描述：

  1,5-戊二醇 、 对氟苄胺 在 C₂₁H₃₅BrMnN₂O₂P 、 potassium hydride 作用下， 以 甲苯 为溶剂， 反应 40.0h， 以52%的产率得到1-[(4-fluorophenyl)methyl]-2,6-piperidinedione
  参考文献：
  名称：

  [EN] MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS
  [FR] COMPLEXES À BASE DE MANGANÈSE ET LEURS UTILISATIONS SERVANT À UNE CATALYSE HOMOGÈNE

  摘要：

  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。

  公开号：

  WO2017137984A1

文献信息

• Synthesis of Cyclic Imides by Acceptorless Dehydrogenative Coupling of Diols and Amines Catalyzed by a Manganese Pincer Complex
  作者：Noel Angel Espinosa-Jalapa、Amit Kumar、Gregory Leitus、Yael Diskin-Posner、David Milstein

  DOI：10.1021/jacs.7b08341

  日期：2017.8.30

  base-metal-catalyzed dehydrogenative coupling of diols and amines to form cyclic imides is reported. The reaction is catalyzed by a pincer complex of the earth abundant manganese and forms hydrogen gas as the sole byproduct, making the overall process atom economical and environmentally benign.

  报告了碱金属催化的二醇和胺脱氢偶联形成环状酰亚胺的第一个例子。该反应由地球上丰富的锰的钳形络合物催化，并形成氢气作为唯一的副产品，使整个过程原子经济且环保。
• MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS
  申请人：Yeda Research and Development Co. Ltd

  公开号：EP3919466A1

  公开（公告）日：2021-12-08

  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.

  本发明涉及新型锰络合物及其在以下方面的均相催化等用途：(1)通过醇和胺的脱氢偶联制备亚胺；(2)在迈克尔加成反应中使用腈作为迈克尔供体的C-C偶联；(3) 醇的脱氢偶联生成酯和氢气 (4) 酯的氢化生成醇（包括环酯（内酯）或环二酯（二内酯）或聚酯的氢化）；(5) 将酰胺（包括环状二肽、内酰胺、二酰胺、多肽和多酰胺）氢化成醇和胺（或 二胺）；(6) 将有机碳酸盐（包括聚碳酸酯）氢化成醇，或将氨基甲酸酯（包括聚氨基甲 酸酯）或脲衍生物氢化成醇和胺；(7) 将仲醇脱氢成酮；(8) 酯的酰胺化（即酰胺化）。e.,(10) 醇与水和碱偶联生成羧酸；以及 (11) 通过氨基醇与水和碱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、多肽和多酰胺）； (13) 利用二元醇制备亚胺。
• [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。