1-quinolin-3-yl-pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-quinolin-3-yl-pyrrolidin-2-one
• 英文别名: 1-quinolin-3-ylpyrrolidin-2-one
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: IYXJVKLYRMWVBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-quinolin-3-yl-pyrrolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以40%的产率得到3-(pyrrolidin-1-yl)quinoline
  参考文献：
  名称：

  经由中间体（3-吡咯啉-1-基）-和（2-氧吡咯烷基-1-基）喹啉合成功能化的3-，5-，6-和8-氨基喹啉并评估其抗血浆和抗真菌活性

  摘要：

  （3-吡咯啉-1-基） -和（2-氧代吡咯烷-1-基）喹啉制备经由diallylaminoquinolines和4-氯环化Ñ -quinolinylbutanamides分别作为新的合成中间体途中到Ñ功能化的3、5、6和8氨基喹啉具有潜在的生物活性。（3-吡咯啉-1-基）喹啉经过溴化反应后，评估了（2-氧吡咯烷-1-基）喹啉对氢化铝锂和甲基锂的反应性，为广泛的新型功能化（吡咯烷-1-基）-和（羟烷基氨基）喹啉。对这些新型喹啉及其功能化衍生物的抗血浆评价表明，它对疟疾寄生虫恶性疟原虫的氯喹敏感菌株具有中等微摩尔效价，并且两种最有效的化合物还对恶性疟原虫的抗氯喹菌株具有微摩尔活性。。对（羟烷基氨基）喹啉类药物的抗真菌评估显示，三种化合物具有对抗Bogoriensis的MIC值和一种具有有效抗黄曲霉活性的化合物。

  DOI：

  10.1016/j.ejmech.2014.12.020
• 作为产物：
  描述：

  3-氨基喹啉 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 1-quinolin-3-yl-pyrrolidin-2-one
  参考文献：
  名称：

  经由中间体（3-吡咯啉-1-基）-和（2-氧吡咯烷基-1-基）喹啉合成功能化的3-，5-，6-和8-氨基喹啉并评估其抗血浆和抗真菌活性

  摘要：

  （3-吡咯啉-1-基） -和（2-氧代吡咯烷-1-基）喹啉制备经由diallylaminoquinolines和4-氯环化Ñ -quinolinylbutanamides分别作为新的合成中间体途中到Ñ功能化的3、5、6和8氨基喹啉具有潜在的生物活性。（3-吡咯啉-1-基）喹啉经过溴化反应后，评估了（2-氧吡咯烷-1-基）喹啉对氢化铝锂和甲基锂的反应性，为广泛的新型功能化（吡咯烷-1-基）-和（羟烷基氨基）喹啉。对这些新型喹啉及其功能化衍生物的抗血浆评价表明，它对疟疾寄生虫恶性疟原虫的氯喹敏感菌株具有中等微摩尔效价，并且两种最有效的化合物还对恶性疟原虫的抗氯喹菌株具有微摩尔活性。。对（羟烷基氨基）喹啉类药物的抗真菌评估显示，三种化合物具有对抗Bogoriensis的MIC值和一种具有有效抗黄曲霉活性的化合物。

  DOI：

  10.1016/j.ejmech.2014.12.020

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• 2,9-diamino- and 2-amino-8-carbamoyl-4-hydroxy-alkanoic acid amide
  申请人：Novartis Corporation

  公开号：US05719141A1

  公开（公告）日：1998-02-17

  Compounds of the formula I ##STR1## in which R.sub.1 is arylamino, N-aryl-N-(lower alkoxy-lower alkyl)-amino, N-aryl-N-aryl-lower alkyl-amino or heterocyclyl bonded via a ring carbon atom, X is a carbonyl or methylene group, R.sub.2 and R.sub.3 independently of one another are hydrogen or lower alkyl or, together with the carbon atom with which they are bonded, are a cycloalkylidene radical, R.sub.4 is hydrogen, lower alkyl, lower alkanoyl or lower alkoxycarbonyl, R.sub.5 is hydroxyl, lower alkanoyloxy or lower alkoxycarbonyloxy, R.sub.6 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, cycloalkyl-lower alkyl, aryl-lower alkyl or heteroaryl-lower alkyl having 5 to 7 ring atoms in the heteroaryl ring and R.sub.7 is hydrogen or lower alkyl, or R.sub.6 and R.sub.7, together with the carbon atom with which they are bonded, are a cydoalkylidene radical and R.sub.8 denotes an aliphatic, cycloaliphatic-aliphatic or heteroarylaliphatic radical, and their salts can be used as active ingredients for medicaments for treatment of high blood pressure.

  公式I的化合物##STR1##中，其中R.sub.1是芳基氨基，N-芳基-N-(较低烷氧基-较低烷基)-氨基，N-芳基-N-芳基-较低烷基-氨基或通过环碳原子连接的杂环基，X是羰基或亚甲基基团，R.sub.2和R.sub.3彼此独立地是氢或较低烷基，或者与它们连接的碳原子一起是环烷基亚甲基基团，R.sub.4是氢，较低烷基，较低烷酰基或较低烷氧羰基，R.sub.5是羟基，较低烷酰氧基或较低烷氧羰氧基，R.sub.6是氢，较低烷基，较低烯基，较低炔基，环烷基，环烷基-较低烷基，芳基-较低烷基或杂环芳基-较低烷基，在杂环芳基环中有5到7个环原子，R.sub.7是氢或较低烷基，或者R.sub.6和R.sub.7与它们连接的碳原子一起是环烷基亚甲基基团，R.sub.8表示脂肪，环脂肪-脂肪或杂环脂肪基团，它们的盐可用作治疗高血压药物的活性成分。
• A General and Efficient Copper Catalyst for the Amidation of Aryl Halides
  作者：Artis Klapars、Xiaohua Huang、Stephen L. Buchwald

  DOI：10.1021/ja0260465

  日期：2002.6.1

  was developed for the amidation of aryl halides by using 0.2-10 mol % of CuI, 5-20 mol % of a 1,2-diamine ligand, and K(3)PO(4), K(2)CO(3), or Cs(2)CO(3) as base. Catalyst systems based on N,N'-dimethylethylenediamine or trans-N,N'-dimethyl-1,2-cyclohexanediamine were found to be the most active even though several other 1,2-diamine ligands could be used in the easiest cases. Aryl iodides, bromides, and

  通过使用 0.2-10 mol% 的 CuI、5-20 mol% 的 1,2-二胺配体和 K(3)PO(4), K (2)CO(3) 或 Cs(2)CO(3) 作为碱。发现基于 N,N'-二甲基乙二胺或反式-N,N'-二甲基-1,2-环己二胺的催化剂体系是最活跃的，尽管在最简单的情况下可以使用其他几种 1,2-二胺配体。芳基碘化物、溴化物，在某些情况下甚至芳基氯化物都可以有效地酰胺化。反应中可以容忍多种官能团，包括许多与 Pd 催化的酰胺化或胺化方法不兼容的官能团。
• Copper-catalyzed formation of carbon heteroatom and carbon-carbon bonds
  申请人：Buchwald L. Stephen

  公开号：US20050215794A1

  公开（公告）日：2005-09-29

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和酰胺或胺基团的氮原子之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和酰肼的氮原子之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和含氮杂环芳香族化合物（例如吲哚、吡唑和吲唑）的氮原子之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和醇的氧原子之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子（例如烯醇酸根离子或马隆酸根离子）的反应物和苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价易行。
• Copper-catalyzed formation of carbon-heteroatom and carbon—carbon bonds
  申请人：Buchwald Stephen L.

  公开号：US09067955B2

  公开（公告）日：2015-06-30

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods, such as the reaction of Z-X with C(L)(R)(R′)2 in the present of a catalyst and a base, thereby forming C(Z)(R)(R′)2; wherein X represents I, Cl, alkylsulfonate, or arylsulfonate; Z represents optionally substituted aryl, heteroaryl or alkenyl; L represents H or a negative charge; catalyst comprises a copper atom or ion, and a ligand, wherein the ligand is an optionally substituted aryl alcohol, alkyl amine, 1,2-diamine, 1,2-aminoalcohol, 1,2-diol, imidazolium carbene, pyridine, or 1,10-phenanthroline; the ligand is a chelating ligand; and the base represents a Bronsted base; R represents H, optionally substituted alkyl, cycloalkyl, aralkyl, aryl, or heteroaryl; R′ represents independently for each occurrence H, alkyl, cycloalkyl, aralkyl, aryl, or heteroaryl, formyl, acyl, —CO2R″, —C(O)N(R)2, sulfonyl, —P(O)(OR″)2, —CN, or —NO2; R″ represents independently for each occurrence optionally substituted alkyl, cycloalkyl, aralkyl, aryl, or heteroaryl; and C(R′)2(R) taken together may represent nitrile.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法，例如在催化剂和碱的存在下，Z-X与C（L）（R）（R'）2反应，从而形成C（Z）（R）（R'）2；其中X代表I，Cl，烷基磺酸盐或芳基磺酸盐；Z代表可选取代的芳基，杂原芳基或烯丙基；L代表H或负电荷；催化剂包括铜原子或离子和配体，其中配体是可选取代的芳基醇，烷基胺，1,2-二胺，1,2-氨基醇，1,2-二醇，咪唑卡宾，吡啶或1,10-菲啰啉；配体是螯合配体；碱代表布朗斯特德碱；R代表H，可选取代的烷基，环烷基，芳基烷基，芳基或杂原芳基；R'代表独立地为每个出现的H，烷基，环烷基，芳基烷基，芳基或杂原芳基，甲酰基，酰基，-CO2R″，-C（O）N（R）2，磺酰基，-P（O）（OR″）2，-CN或-NO2；R″代表独立地为每个出现的可选取代的烷基，环烷基，芳基烷基，芳基或杂原芳基；而C（R'）2（R）在一起可以代表腈。