N-(cyclopropylmethyl)picolinamide | 1110833-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(cyclopropylmethyl)picolinamide
• 英文别名: N-(cyclopropylmethyl)pyridine-2-carboxamide
• CAS: 1110833-69-6
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: WYMABUOOTPGANC-UHFFFAOYSA-N

物化性质

• 沸点：
  395.9±15.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(cyclopropylmethyl)picolinamide 在 乙酸-D1 、 palladium diacetate 作用下， 以 氘代苯 为溶剂， 反应 15.0h， 生成 N-(cyclopropylmethyl)picolinamide
  参考文献：
  名称：

  C–H Functionalization of Cyclopropanes: A Practical Approach Employing a Picolinamide Auxiliary

  摘要：

  A Pd-catalyzed, picolinamide-enabled, and efficient C-H arylation of cyclopropanes is described. The reaction can be promoted by either a silver additive or catalytic pivalic acid in the presence of a carbonate base. Various aryl iodides can be employed as coupling partners, providing exclusively cis-substituted cyclopropylpicolinamides.

  DOI：

  10.1021/ol401931s
• 作为产物：
  描述：

  2-吡啶甲酸乙酯 、 环丙基甲胺 在 lanthanum(lll) triflate 作用下， 反应 1.0h， 以98%的产率得到N-(cyclopropylmethyl)picolinamide
  参考文献：
  名称：

  Lanthanum(III) Triflate Catalyzed Direct Amidation of Esters

  摘要：

  Lanthanum trifluoromethanesulfonate is an effective single-component catalyst for synthesizing a variety of amides directly from esters and amines under mild conditions. Highly selective amidation of esters and amines, as well as catalyst-controlled amidation of esters, demonstrated the effectiveness of the catalyst system.

  DOI：

  10.1021/ol500593v

文献信息

• Chelation-promoted Efficient C−H/N−H Cross Dehydrogenative Coupling between Picolinamides and Simple Ethers under Copper Catalysis
  作者：Qiang Yue、Zhen Xiao、Zhengkun Kuang、Zhengding Su、Qian Zhang、Dong Li

  DOI：10.1002/adsc.201701508

  日期：2018.3.20

  A highly efficient copper‐catalyzed C−H/N−H cross dehydrogenative coupling between picolinamides and simple ethers was developed. The reaction was promoted by the chelation assistance of removable picolinyl group and exhibited excellent TON and TOF number. This method was applicable to both N‐aryl and alkyl picolinamides as well as various cyclic and acyclic ethers with good functional group compatibility

  在吡啶甲酰胺和简单醚之间开发了一种高效的铜催化CH / NH交叉脱氢偶联剂。可移动的吡啶基的螯合辅助促进了反应，并显示出优异的TON和TOF值。该方法适用于N-芳基和烷基吡啶甲基酰胺以及具有良好官能团相容性的各种环状和无环醚。它还具有耐空气和潮湿的优点，并且易于操作。
• [EN] AZETIDINES AND CYCLOBUTANES AS HISTAMINE H3 RECEPTOR ANTAGONISTS<br/>[FR] AZÉTIDINES ET CYCLOBUTANES COMME ANTAGONISTES DES RÉCEPTEURS H3 DE L'HISTAMINE
  申请人：EVOTEC NEUROSCIENCES GMBH

  公开号：WO2009135842A1

  公开（公告）日：2009-11-12

  The invention relates to compounds of formula (I) wherein R, R0, R1, m, n and X1 to X4 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention also relates to pharmaceutical compositions, the preparation of such compounds as well as the production and use as medicament.

  本发明涉及具有式(I)的化合物，其中R，R0，R1，m，n和X1至X4如描述和权利要求中所引述的含义。所述化合物作为组胺H3受体拮抗剂是有用的。本发明还涉及药物组合物，以及此类化合物的制备以及作为药品的生产和使用。
• Diastereoselective Pd(II)-Catalyzed sp³C–H Arylation Followed by Ring Opening of Cyclopropanecarboxamides: Construction of<i>anti</i>β-Acyloxy Carboxamide Derivatives
  作者：Bojan Gopalakrishnan、Sruthi Mohan、Ramarao Parella、Srinivasarao Arulananda Babu

  DOI：10.1021/acs.joc.6b01635

  日期：2016.10.7

  diastereoselective Pd(OAc)2-catalyzed, bidentate ligand-directed sp3 C–H activation/arylation followed by ring opening of cyclopropanecarboxamides, which were assembled from cyclopropanecarbonyl chlorides and bidentate ligands (e.g., 8-aminoquinoline and 2-(methylthio)aniline), has been investigated. The treatment of various cyclopropanecarboxamides with excess amounts of aryl iodides in the presence of the Pd(OAc)2

  非对映选择性的Pd（OAc）2催化的，双齿配体导向的sp 3 C–H活化/芳基化反应，然后环丙烷甲酰胺的开环，环丙烷甲酰胺由环丙烷羰基氯化物和双齿配体（例如8-氨基喹啉和2-（甲硫基）组装而成）苯胺），已被调查。在Pd（OAc）2催化剂，AgOAc和AcOH存在下，用过量的芳基碘化物处理各种环丙烷甲酰胺可直接提供相应的多个β-CHH芳基化开链羧酰胺（抗β-酰氧基酰胺）。这种方法导致了几种反构造具有邻位立体中心且高度立体控制的β-酰氧基酰胺，形成一个新的C-O键和三个新的C-C键。基于一些控制实验，提出了由Pd催化，双齿配体定向的β-C-H芳基化和环丙烷甲酰胺的开环形成多种β-CHH芳基化开链羧酰胺的合理机制。基于代表性的β-酰氧基酰胺的X射线结构分析，确定了观察到的β-酰氧基酰胺的非对映选择性和抗立体化学。
• Iridium(III)-Catalyzed Intermolecular Mild N-Arylation of Aliphatic Amides Using Quinoid Carbene: A Migratory Insertion-Based Approach
  作者：Satabdi Bera、Saikat Roy、Shyam Chand Pal、Anakuthil Anoop、Rajarshi Samanta

  DOI：10.1021/acscatal.1c02653

  日期：2021.9.3

  An efficient Ir(III)-catalyzed straightforward intermolecular N-arylation of acyclic aliphatic amides has been achieved using quinone diazide as a coupling partner. The reaction has been developed under simple and mild reaction conditions with a broad substrate scope. The bidentate picolinamide group is essential for successful transformation. Mechanistic studies and DFT calculations highlighted the

  使用二叠氮醌作为偶联伙伴已经实现了有效的 Ir(III) 催化的无环脂肪族酰胺的直接分子间 N-芳基化。该反应在简单温和的反应条件下进行，底物范围广泛。双齿吡啶甲酰胺基团对于成功转化至关重要。机理研究和 DFT 计算突出了基于迁移插入的途径。与使用相关重氮/叠氮化物同系物在 Rh(III)/Ir(III) 催化下的无环脂肪族酰胺反应相比，所开发的方法表现出不同的反应性。
• Rh(<scp>iii</scp>)-catalyzed regioselective intermolecular <i>N</i>-methylene Csp³–H bond carbenoid insertion
  作者：Haisheng Xie、Zongren Ye、Zhuofeng Ke、Jianyong Lan、Huanfeng Jiang、Wei Zeng

  DOI：10.1039/c7sc03802j

  日期：——

  A Rh(III)-catalyzed regioselective intermolecular carbenoid insertion into the N-methylene Csp3–H bond of acyclic aliphatic amides has been achieved, taking advantage of bidentate–chelation assistance. This methodology has been successfully applied to a broad range of linear and branched-chain N-alkylamides, thus providing a practical method for the assembly of diverse beta-amino esters. Mechanism

  利用二齿螯合的辅助作用，实现了Rh（III）催化的区域选择性分子间类胡萝卜素插入无环脂族酰胺的N-亚甲基Csp 3 -H键中。该方法已经成功地应用于各种线性和支链的N-烷基酰胺，因此为组装各种β-氨基酯提供了一种实用的方法。机理研究和密度泛函理论（DFT）计算表明，这种N-亚甲基Csp 3 -H键类胡萝卜素插入过程涉及通过外球途径的单线Fischer型卡宾插入。