2-(hex-1-yn-1-yl)-4-methylaniline | 928782-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(hex-1-yn-1-yl)-4-methylaniline
• 英文别名: 2-(hex-1-ynyl)-4-methylaniline；2-Hex-1-ynyl-4-methylaniline
• CAS: 928782-89-2
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: BIPNBGNUPLVWTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(hex-1-yn-1-yl)-4-methylaniline 在 哌啶 、 亚碘酰苯 、 silver trifluoromethanesulfonate 、 <15N>glycine ethyl ester hydrochloride 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 20.08h， 生成 2-butyl-5-methyl-1H-indole-¹⁵N
  参考文献：
  名称：

  Synthesis of ¹⁵N-labeled heterocycles via the cleavage of C–N bonds of anilines and glycine-¹⁵N

  摘要：

  一种通过甘氨酸-¹⁵N替代苯胺的氮替换过程，通过断裂两个C-N键合成¹⁵N标记的芳香杂环化合物。

  DOI：

  10.1039/d1cc01734a
• 作为产物：
  描述：

  2-溴-4-甲基苯胺 、 1-己炔 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 反应 48.0h， 以41%的产率得到2-(hex-1-yn-1-yl)-4-methylaniline
  参考文献：
  名称：

  多组分级联反应：前所未有的亲核加成-杂环化-氧化性烷氧羰基化序列的功能化吲哚的一种新颖，简便的方法。

  摘要：

  据报道，基于对亚胺部分的初始亲核攻击步骤与钯催化的氧化杂环-烷氧羰基化过程之间的顺序组合，提出了一种新颖的多组分级联过程。通过这一新方法，五个简单分子[2-炔基苯胺亚胺，醇（ROH），一氧化碳（CO），醇（ROH）和氧（O 2）]被依次激活，选择性地导致高附加值的功能化吲哚一次操作中的派生。

  DOI：

  10.1002/adsc.201000642

文献信息

• PtCl2-catalyzed reactions of o-alkynylanilines with ethyl propiolate and dimethyl acetylenedicarboxylate
  作者：Xun Li、Jun-Yan Wang、Wei Yu、Long-Min Wu

  DOI：10.1016/j.tet.2008.11.095

  日期：2009.2

  The PtCl2-catalyzed reactions between indoles and ethyl propiolate gave rise to mono and double addition products. The composition of the products was largely influenced by the substituents on the indoles as well as the amount of ethyl propiolate used. o-Alkynylanilines reacted with ethyl propiolate and dimethyl acetylenedicarboxylate under the catalysis of PtCl2 to generate the corresponding 2,3-disubstituted

  吲哚和丙酸乙酯之间的PtCl 2催化反应产生单加成产物和双加成产物。产物的组成在很大程度上受到吲哚上的取代基以及丙酸乙酯用量的影响。在PtCl 2的催化下，邻炔基苯胺与丙酸乙酯和乙酰二羧酸二甲酯反应，生成相应的2,3-二取代的吲哚。通过遵循顺序的环化/分子间加成途径来进行反应。
• Synthesis of <i>N</i>-Azolylindoles by Copper-Catalyzed C–H/N–H Coupling–Annulation Sequence of <i>o</i>-Alkynylanilines
  作者：Yoshiro Oda、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol203392r

  日期：2012.1.20

  A wide range of o-alkynylanilines undergo a copper-catalyzed direct C-H/N-H coupling with azoles followed by benzannulation to form the corresponding N-azolylindoles in good yields. The domino reaction proceeds effectively with molecular oxygen as the sole oxidant and provides a new dehydrogenative access to the titled compounds of interest in pharmaceutical and material sciences.
• An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles
  作者：Naoki Matsuda、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo202207s

  日期：2012.1.6

  A copper-catalyzed annulative amination approach to 3-aminobenzofurans and -indoles from o-alkynylphenols and -anilines has been developed. The Cu-based catalysis is based on an umpolung, electrophilic amination with O-benzoyl hydroxylamines and enables the mild and convergent synthesis of various 3-aminobenzoheteroles of biological and pharmaceutical interest. Some mechanistic investigations and an application of this protocol to construction of more complex tricyclic framework are also described.
• Crossover-Annulation/Oxygenation Approach to Functionalized Phenanthridines by Palladium–Copper Relay Catalysis
  作者：Xiang Liu、Renjie Mao、Cheng Ma

  DOI：10.1021/acs.orglett.7b03427

  日期：2017.12.15

  A tandem crossover-annulation and oxygenation process of conjugated enediyne-acids and ortho-alkynylanilines was achieved by palladium-copper relay catalysis under an oxygen atmosphere, giving access to the three-component assembly of 9-acylphenanthridine compounds.
• Multicomponent Cascade Reactions: A Novel and Expedient Approach to Functionalized Indoles by an Unprecedented Nucleophilic Addition-Heterocyclization-Oxidative Alkoxycarbonylation Sequence
  作者：Bartolo Gabriele、Lucia Veltri、Giuseppe Salerno、Raffaella Mancuso、Mirco Costa

  DOI：10.1002/adsc.201000642

  日期：2010.12.17

  A novel multicomponent cascade process is reported, based on the sequential combination between an initial nucleophilic attack step to an imine moiety and a palladium-catalyzed oxidative heterocyclization-alkoxycarbonylation process. By this new process, five simple molecules [2-alkynylaniline imines, alcohol (ROH), carbon monoxide (CO), alcohol (ROH), and oxygen (O2)] are sequentially activated, selectively

  据报道，基于对亚胺部分的初始亲核攻击步骤与钯催化的氧化杂环-烷氧羰基化过程之间的顺序组合，提出了一种新颖的多组分级联过程。通过这一新方法，五个简单分子[2-炔基苯胺亚胺，醇（ROH），一氧化碳（CO），醇（ROH）和氧（O 2）]被依次激活，选择性地导致高附加值的功能化吲哚一次操作中的派生。