tert-butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate | 1284210-49-6

• 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: tert-butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate
• 英文别名: t-Butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate；tert-butyl N-prop-2-ynyl-N-pyridin-2-ylcarbamate
• CAS: 1284210-49-6
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: MCMFGNXJKZCENO-UHFFFAOYSA-N

物化性质

• 沸点：
  327.0±22.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate 在 三氟乙酸 、 copper dichloride 、 亚硝酸异戊酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 咪唑并[1,2-a]吡啶-3-甲醛
  参考文献：
  名称：

  从N-（prop-2-yn-1-yl）pyridin-2-amines合成咪唑并[1,2-a]吡啶的实用两步法。

  摘要：

  不同C-2取代的N-（prop-2-yn-1-ylamino）吡啶的Sandmeyer反应是一种高效，温和，新颖且实用的立体异构合成带有咪唑的（E）-exo-卤代亚甲基双环吡啶酮的方法[1,2-a]吡啶杂环系统。

  DOI：

  10.1039/c1cc10641d
• 作为产物：
  描述：

  2-氨基吡啶 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 11.0h， 生成 tert-butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate
  参考文献：
  名称：

  Design, synthesis, and evaluation of hinge-binder tethered 1,2,3-triazolylsalicylamide derivatives as Aurora kinase inhibitors

  摘要：

  A series of hinge-binder tethered 1,2,3-triazolylsalicylamide derivatives were designed, synthesized, and evaluated for the Aurora kinase inhibitory activities. The novel hinge-binder tethered 1,2,3-triazolylsalicylamide scaffold was effectively assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC). A variety of alkynes with hinge binders were used to search proper structures-binding relationship to the hinge region. The synthesized 1,2,3-triazolylsalicylamide derivatives showed significant Aurora kinase inhibitory activity. In particular, 8a inhibited Aurora A kinase with an IC50 value of 0.284 mu M, whereas 8m inhibited Aurora B kinase with an IC50 value of 0.364 mu M. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.042

文献信息

• Silver-assisted palladium-catalyzed one-pot synthesis of 3-(hetero)arylmethyl derivatives of imidazo[1,2-a]pyridines
  作者：Krishna Chaitanya Kasina、Siva Kumar Rapeti、Arghya Sadhukhan、Mahesh Ranga、Arani Pal、Saritha Birudaraju、Siva rao Tirukkovalluri

  DOI：10.1007/s10593-021-02941-3

  日期：2021.5

  3-(Hetero)arylmethyl derivatives of imidazo[1,2-a]pyridine have been synthesized by a novel one-pot method consisting of the Sonogashira coupling of tert-butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate with different substituted (hetero)aryl bromides and cyclization of the in situ obtained intermediate substituted (hetero)aryl acetylene derivatives.

  咪唑并[1,2- a ]吡啶的3-（杂）芳甲基衍生物已通过一种新型的一锅法合成，该方法由叔丁基丙-2-yn-1-基（吡啶-2-）的Sonogashira偶联组成。基)氨基甲酸酯与不同的取代(杂)芳基溴化物和原位环化得到中间体取代的(杂)芳基乙炔衍生物。
• Silver-Catalyzed Cyclization of<i>N</i>-(Prop-2-yn-1-yl)pyridin-2-amines
  作者：Mourad Chioua、Elena Soriano、Lourdes Infantes、M. Luisa Jimeno、José Marco-Contelles、Abdelouahid Samadi

  DOI：10.1002/ejoc.201201258

  日期：2013.1

  We report herein the silver-catalyzed cycloisomerization of readily available N-(prop-2-yn-1-yl)pyridine-2-amines as a new and practical method for the synthesis of differently substituted 3-methylimidazo[1,2-a]pyridines. The isomerization reactions proceeded under mild reactions conditions to give good yields and excellent regioselectivity. A DFT-based mechanistic analysis is also reported.

  我们在此报告了银催化的易于获得的 N-(prop-2-yn-1-yl)pyridine-2-amines 的环异构化作为合成不同取代的 3-methylimidazo[1,2-a ]吡啶。异构化反应在温和的反应条件下进行，具有良好的产率和优异的区域选择性。还报告了基于 DFT 的机械分析。
• 신규한 트리아졸 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 오로라 키나제 관련 약학적 조성물
  申请人：Ewha University - Industry Collaboration Foundation 이화여자대학교 산학협력단(220040083301) BRN ▼110-82-10456

  公开号：KR101723881B1

  公开（公告）日：2017-04-07

  본 발명은 신규한 트리아졸 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 오로라 키나제 관련 약학적 조성물에 관한 것으로, 본 발명에 따른 신규한 트리아졸 유도체, 이의 광학 이성질체, 또는 이의 약학적으로 허용 가능한 염은, 오로라 키나제로써 나노몰 단위의 우수한 저해활성을 나타내며, 이를 함유하는 약학적 조성물로써 다양한 암 또는 종양의 치료에 유용한 효과가 있다.

  本发明涉及一种新的三唑衍生物，其制备方法及其作为有效成分包含在含有Aurora激酶相关药物的制剂中，根据本发明的新三唑衍生物，其光学异构体或其药学上可接受的盐，通过Aurora激酶表现出优异的纳摩尔单位的抑制活性，并且作为含有该化合物的药学制剂在治疗各种癌症或肿瘤方面具有有益效果。
• A multicomponent palladium-catalyzed carbonylative approach to imidazopyridinyl-N,N-dialkylacetamides
  作者：Lucia Veltri、Patrizio Russo、Tommaso Prestia、Paola Vitale、Roberto Romeo、Bartolo Gabriele

  DOI：10.1016/j.jcat.2020.03.026

  日期：2020.6

  A novel, multicomponent approach to 2-(imidazo[1,2-a]pyridin-3-yl)-N,N-dialkylacetamides (very important class of fused heterocyclic derivatives, known to act on central nervous system by enhancing the activity of the GABA) is reported. It is based on the carbonylation reaction of N-Boc-(prop-2-yn-1yl)pyridin-2-amines carried out in the presence of secondary amines (2-3 equiv) under oxidative conditions, using oxygen (from air) as oxidant (4:1 CO-air, total pressure 20 atm) and PdI2/KI as the catalytic system (0.33-1 mol% of PdI2 and 0.5 equiv of KI) in MeCN as the solvent at 100 degrees C. The process leads to the target compounds in good to high yields (67-90%) through an ordered sequence of steps, occurring in situ under the reaction conditions: Boc-deprotection of the substrate is followed by PdI2/KI-catalyzed oxidative monoaminocarbonylation of the terminal triple bond (or vice versa) to give a 2-ynamide intermediate, which then undergoes intramolecular aza-Michael reaction and isomerization. (C) 2020 Elsevier Inc. All rights reserved.
• Water mediated deprotective intramolecular hydroamination of N-propargylaminopyridines: synthesis of imidazo[1,2-a]pyridines
  作者：Darapaneni Chandra Mohan、Niraj B. Sarang、Subbarayappa Adimurthy

  DOI：10.1016/j.tetlet.2013.08.112

  日期：2013.11

  Metal-free synthesis of substituted imidazole [1,2-alpha]dpyridines from deprotective N-(prop-2-yn-1-yl)pyridin-2-amines in water is elucidated. Electron releasing substituents on pyridine ring provided pure products in quantitative yields without separation by column chromatography. (C) 2013 Elsevier Ltd. All rights reserved.