cyclo isoleucylisoleucyl

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cyclo isoleucylisoleucyl
• 英文别名: 3.6-Di-sek.butyl-piperazin-2,5-dion；3,6-di-sec-butyl-piperazine-2,5-dione；3,6-Di-sec-butyl-piperazin-2,5-dion；3,6-Di-sec-butylpiperazine-2,5-dione；3,6-di(butan-2-yl)piperazine-2,5-dione
• 化学式: C₁₂H₂₂N₂O₂
• 分子量: 226.319
• InChiKey: ZRLVJNQOEORYIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclo isoleucylisoleucyl 在 氢氧化钾 、 三氯氧磷 作用下， 生成 2(1H)-吡嗪酮,3,6-二(1-甲基丙基)-
  参考文献：
  名称：

  221.吡嗪衍生物。第三部分 将二酮哌嗪转化为吡嗪衍生物。6-二- ：2-羟基3的合成秒从。-butylpyrazine异亮氨酸

  摘要：

  DOI：

  10.1039/jr9470001179
• 作为产物：
  描述：

  isoleucine 在 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 cyclo isoleucylisoleucyl
  参考文献：
  名称：

  氨基酸与三氯化磷反应机理的31P NMR和ESI-MS / MS研究

  摘要：

  通过31 P NMR示踪和ESI-MS / MS研究了氨基酸与三氯化磷在THF中的反应。获得了一系列的氢杂环丙烷和环状二肽。反应呈现出有趣的多样性，并提出了反应机理。该机理表明磷在氨基酸氢庚烷和环状二肽的合成中起着重要作用。结果还表明，31 P NMR和ESI-MS / MS是研究反应机理的有用工具。

  DOI：

  10.1002/cjoc.201190219

文献信息

• Studies on pyrazines. Part 32. Synthesis of trisubstituted and tetrasubstituted pyrazines as ant pheromones
  作者：Nobuhiro Sato、Tomoyuki Matsuura

  DOI：10.1039/p19960002345

  日期：——

  The synthesis of trialkylpyrazines having methyl groups on C-2 and C-5 is described, which is completed by the cross-coupling reaction of 2-chloro-3,6-dimethylpyrazine with dialkylzinc in the presence of [1,3-bis(diphenylphosphino)propane] nickel(II) chloride. Similarly, 2,5-diisobutyl-, -diisopropyl- and -di-sec-butyl-3-methylpyrazines are prepared from the corresponding dialkyl chloropyrazines. The dimethyl products are acylated with an α-keto acid under the Minisci radical conditions providing 2-acyl-5-alkyl-3,6-dimethylpyrazines. Several compounds obtained in this study prove to be active as components of pheromones in ants.

  本文描述了具有C-2和C-5位甲基的三烷基吡嗪的合成方法，该合成通过2-氯-3,6-二甲基吡嗪与二烷基锌在[1,3-双(二苯基膦基)丙烷]镍(II)氯化物的催化下进行交叉耦合反应完成。类似地，从相应的二烷基氯吡嗪制备了2,5-二异丁基-、二异丙基-和二仲丁基-3-甲基吡嗪。二甲基产物通过Minisci自由基条件下与α-酮酸的酰化反应，得到了2-酰基-5-烷基-3,6-二甲基吡嗪。本研究中得到的几种化合物证实作为蚂蚁信息素的组成部分具有活性。
• USE OF RUTHENIUM COMPLEXES FOR FORMATION AND/OR HYDROGENATION OF AMIDES AND RELATED CARBOXYLIC ACID DERIVATIVES
  申请人：Milstein David

  公开号：US20120253042A1

  公开（公告）日：2012-10-04

  A process for preparing amides by reacting a primary amine and a primary alcohol in the presence of a Ruthenium complex to generate the amide and molecular hydrogen. Primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. Also disclosed are processes for hydrogenation of amides to alcohols and amines; hydrogenation of organic carbonates to alcohols; hydrogenation of carbamates or urea derivatives to alcohols and amines; amidation of esters; acylation of alcohols using esters; coupling of alcohols with water and a base to form carboxylic acids; dehydrogenation of beta-amino alcohols to form pyrazines and cyclic dipeptides; and dehydrogenation of secondary alcohols to ketones. These reactions are catalyzed by a Ruthenium complex which is based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3.

  一种制备酰胺的方法，包括在Ruthenium配合物的存在下，通过反应一种一级胺和一种一级醇生成酰胺和分子氢。直接用等摩尔量的醇对一级胺进行酰化反应，可以高产率、高周转数地生成酰胺和分子氢（唯一的副产物）。此外，还揭示了将酰胺氢化为醇和胺的方法；将有机碳酸酯氢化为醇的方法；将氨基甲酸酯或尿素衍生物氢化为醇和胺的方法；酯的酰胺化反应；使用酯对醇进行酰化反应；将醇与水和碱偶联形成羧酸；将β-氨基醇脱氢生成吡嗪和环肽；以及将二级醇脱氢生成酮的方法。这些反应由基于A1式或A2式或A3式的去芳香的PNN型配体的Ruthenium配合物催化。
• Ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof
  申请人：Milstein David

  公开号：US09045381B2

  公开（公告）日：2015-06-02

  The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e., synthesis of amides from esters and amines); (8) acylation of alcohols using esters; (9) coupling of alcohols with water to form carboxylic acids; and (10) dehydrogenation of beta-amino alcohols to form pyrazines. The present invention further relates to the novel uses of certain pyridine Ruthenium catalysts.

  本发明涉及新型钌催化剂及相关硼氢化物络合物的使用，其中包括以下用途：(1)将酰胺（包括聚酰胺）加氢成为醇和胺；(2)通过醇和胺制备酰胺（包括通过双醇和双胺反应制备聚酰胺（例如多肽）和通过氨基醇聚合制备聚酰胺）；(3)将酯加氢成为醇（包括环酯（内酯）或环二酯（内二酯）或聚酯的加氢）；(4)将有机碳酸酯（包括聚碳酸酯）加氢成为醇和将氨基甲酸酯（包括聚氨基甲酸酯）或脲衍生物加氢成为醇和胺；(5)将醇脱氢偶合成酯；(6)将二级醇加氢成为酮；(7)酯胺化（即从酯和胺合成酰胺）；(8)使用酯对醇进行酰化；(9)将醇与水偶联形成羧酸；以及(10)将β-氨基醇脱氢成为吡嗪。本发明还涉及某些吡啶钌催化剂的新型用途。
• NOVEL RUTHENIUM COMPLEXES AND THEIR USES IN PROCESSES FOR FORMATION AND/OR HYDROGENATION OF ESTERS, AMIDES AND DERIVATIVES THEREOF
  申请人：Milstein David

  公开号：US20130281664A1

  公开（公告）日：2013-10-24

  The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e., synthesis of amides from esters and amines); (8) acylation of alcohols using esters; (9) coupling of alcohols with water to form carboxylic acids; and (10) dehydrogenation of beta-amino alcohols to form pyrazines. The present invention further relates to the novel uses of certain pyridine Ruthenium catalysts.

  本发明涉及新型钌催化剂和相关硼氢化物配合物，以及使用这些催化剂，包括：（1）将酰胺（包括聚酰胺）加氢为醇和胺；（2）用胺从醇制备酰胺（包括通过二元醇和二胺反应或氨基醇聚合制备聚酰胺（例如聚肽））；（3）将酯加氢为醇（包括环酯（内酯）或环二酯（二内酯）或聚酯的加氢）；（4）将有机碳酸酯（包括聚碳酸酯）加氢为醇和将氨基甲酸酯（包括聚氨基甲酸酯）或脲衍生物加氢为醇和胺；（5）醇的脱氢缩合成酯；（6）将二级醇加氢为酮；（7）酯的酰胺化（即从酯和胺合成酰胺）；（8）使用酯对醇进行酰化；（9）将醇与水偶联形成羧酸；以及（10）β-氨基醇的脱氢缩合形成吡嗪的新用途。本发明还涉及某些吡啶基钌催化剂的新用途。
• Use of ruthenium complexes for formation and/or hydrogenation of amides and related carboxylic acid derivatives
  申请人：Milstein David

  公开号：US09290441B2

  公开（公告）日：2016-03-22

  A process for preparing amides by reacting a primary amine and a primary alcohol in the presence of a Ruthenium complex to generate the amide and molecular hydrogen. Primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. Also disclosed are processes for hydrogenation of amides to alcohols and amines; hydrogenation of organic carbonates to alcohols; hydrogenation of carbamates or urea derivatives to alcohols and amines; amidation of esters; acylation of alcohols using esters; coupling of alcohols with water and a base to form carboxylic acids; dehydrogenation of beta-amino alcohols to form pyrazines and cyclic dipeptides; and dehydrogenation of secondary alcohols to ketones. These reactions are catalyzed by a Ruthenium complex which is based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3.

  一种通过在Ruthenium配合物存在下反应一级胺和一级醇以生成酰胺和分子氢的方法。一级胺可直接与等摩尔量的醇酰化，以高收率和高周转数产生酰胺和分子氢（唯一的副产物）。还公开了将酰胺氢化为醇和胺的方法；将有机碳酸酯氢化为醇的方法；将氨基甲酸酯或脲衍生物氢化为醇和胺的方法；酯的酰胺化；使用酯对醇进行酰化；将醇与水和碱耦合形成羧酸；β-氨基醇的脱氢形成吡嗪和环二肽；以及二级醇的脱氢形成酮。这些反应由基于公式A1的脱芳香PNN型配体或其前体公式A2或A3的Ruthenium配合物催化。