(6-azidohex-1-yn-1-yl)benzene | 856120-87-1

• 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: (6-azidohex-1-yn-1-yl)benzene
• 英文别名: 6-Azidohex-1-ynylbenzene
• CAS: 856120-87-1
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: URTQEHNEBMYRQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6-azidohex-1-yn-1-yl)benzene 在 lithium aluminium tetrahydride 、 tetrakis(acetonitrile)copper(I)tetrafluoroborate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 19.0h， 生成 2-benzyl-3,4,5,6-tetrahydropyridine
  参考文献：
  名称：

  在技​​术条件下用于加氢胺化反应的市售且用户友好的催化剂

  摘要：

  介绍了一种简单的市售铜盐 [Cu(NCMe)4](BF4) 在炔烃和丙二烯的分子内加氢胺化反应中的活性。在空气存在下，在工业乙腈中成功进行了反应。虽然烯烃加氢胺化的尝试失败了，但也发现这种催化剂在分子间氮杂-迈克尔反应中具有活性。

  DOI：

  10.1002/ejoc.201900701
• 作为产物：
  描述：

  (6-溴-己-1-炔基)-苯 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 36.0h， 以92%的产率得到(6-azidohex-1-yn-1-yl)benzene
  参考文献：
  名称：

  An Unprecedented Tandem Annulation of ω-Azido-1-alkynes with Diaryl­iodonium Salts: A Facile Synthesis of Polycyclic Quinolines

  摘要：

  Polysubstituted quinolines are synthesized through an unprecedented cascade annulation of -azido-1-alkynes with diaryliodonium salts, which serve as C2-building blocks. The reaction proceeds smoothly and is catalyzed by Cu(I) catalysts to give various quinolines in good isolated yields with simple operation under mild conditions.

  DOI：

  10.1055/s-0034-1379248

文献信息

• Preparation of 2,3,4,5-Tetrahydropyridines from 5-Alkynylamines Under the Catalytic Action of Gold(III) Salts
  作者：Yukitoshi Fukuda、Kiitiro Utimoto

  DOI：10.1055/s-1991-26621

  日期：——

  Intramolecular addition of amine to carbon-carbon triple bonds in 5-alkynylamines produces 2,3,4,5-tetrahydropyridines under the catalytic action of an aurate salt. Some venom components of various ant species are synthesized by the application of this reaction.

  在金盐的催化作用下，5-烷基胺中的碳-碳三键发生分子内胺加成反应，生成2,3,4,5-四氢吡啶。多种蚁种的某些毒液成分就是通过应用这一反应来合成的。
• Fluoroalkylation–Borylation of Alkynes: An Efficient Method To Obtain (<i>Z</i>)-Tri- and Tetrasubstituted Fluoroalkylated Alkenylboronates
  作者：Wen-Hao Guo、Hai-Yang Zhao、Zhi-Ji Luo、Shu Zhang、Xingang Zhang

  DOI：10.1021/acscatal.8b02842

  日期：2019.1.4

  Efficient methods for the synthesis of fluoroalkylated alkenylboronates are very limited, despite their importance in modern organic synthesis. Herein, we report a palladium-catalyzed trans-fluoroalkylation–borylation of alkynes with fluoroalkyl iodides and B2pin2. The reaction tolerates a series of difluoroalkyl iodides and perfluoroalkyl iodides and can enable coupling with a variety of alkynes,

  尽管在现代有机合成中很重要，但合成氟烷基化烯基硼酸酯的有效方法非常有限。在本文中，我们报道了炔烃与氟代烷基碘化物和B 2 pin 2的钯催化反式-氟代烷基化-硼化。该反应可耐受一系列二氟烷基碘和全氟烷基碘，并且可以与各种炔烃偶联，包括内部和末端炔烃，具有高效，高官能团相容性以及高区域选择性和立体选择性。初步的机理研究表明，反式氟烷基化的烯基碘是关键中间体，其随后进行硼酸酯化以产生反式氟烷基化的烯基硼酸酯。
• The acid-mediated intramolecular 1,3-dipolar cycloaddition of derived 2-nitro-1,1-ethenediamines for the synthesis of novel fused bicyclic isoxazoles
  作者：Lee W. Page、Matthew Bailey、Paul J. Beswick、Simon Frydrych、Robert J. Gleave

  DOI：10.1016/j.tetlet.2010.04.098

  日期：2010.6

  of a novel synthesis of new fused bicyclic isoxazoles, for example, N-methyl-3-phenyl-5,6-dihydro-4H-isoxazolo[3,4-c]azepin-8-amine (2a), N-methyl-3-phenyl-4,5-dihydroisoxazolo[3,4-c]pyridin-7-amine (2b) and N-methyl-3-phenyl-4H-pyrrolo[3,4-c]isoxazol-6-amine (2d) in high yield is reported. We speculate that the reaction proceeds via acid-mediated intramolecular 1,3-dipolar cycloaddition from 2-nitro-1

  发现了一种新的新型稠合双环异恶唑的合成方法，例如，N-甲基-3-苯基-5,6-二氢-4 H-异恶唑并[3,4- c ]氮杂8-胺（2a），N -甲基-3-苯基-4,5-二氢异恶唑[3,4- c ]吡啶-7-胺（2b）和N-甲基-3-苯基-4 H-吡咯并[3,4- c ]异恶唑-6报道了高产率的-胺（2d）。我们推测反应是通过酸介导的分子内1，3-偶极环加成反应从2-硝基-1,1-乙二胺1a，b，d进行的。
• Palladium-catalyzed intramolecular addition of amines to acetylenes. Synthesis of cyclic imines
  作者：Yukitoshi Fukuda、Seijiro Matsubara、Kiitiro Utimoto

  DOI：10.1021/jo00020a023

  日期：1991.9

  Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines. Treatment of 3-alkynylamines with a catalytic amount of PdCl2(MeCN)2 gave exclusively 1-pyrrolines in good yields; 5-alkynylamines afforded 2,3,4,5-tetrahydropyridines selectively. Treatment of 4-alkynylamines with Pd(II) afforded mixtures of both 5- and 6-membered cyclic imines. Applications to the synthesis of some naturally occurring alkaloids are also described.
• Constrained Geometry Organoactinides as Versatile Catalysts for the Intramolecular Hydroamination/Cyclization of Primary and Secondary Amines Having Diverse Tethered C−C Unsaturation
  作者：Bryan D. Stubbert、Tobin J. Marks

  DOI：10.1021/ja0665444

  日期：2007.4.1

  A series of "constrained geometry" organoactinide complexes, (CGC)An(NMe)(2) (CGC = Me2Si(eta(5)-Me4C5)((BuN)-Bu-t); An = Th, 1; U, 2), has been prepared via efficient in situ, two-step protodeamination routes in good yields and high purity. Both 1 and 2 are quantitatively converted to the neutrally charged, solvent-free dichlorides (1-Cl-2, 2-Cl-2) and slightly more soluble diiodides (1-I-2, 2-I-2) with excess Me3Si-X (X = Cl, I) in non-coordinating solvents. The new complexes were characterized by NMR spectroscopy, elemental analysis, and (for 1 and 2) single-crystal X-ray diffraction, revealing substantially increased metal coordinative unsaturation vs the corresponding Me2SiCp ''(2)AnR(2) (Cp '' = eta(5)-Me4C5; An = Th, R = CH2(SiMe3), 3; An = U, R = CH2Ph, 4) and Cp'(2)AnR(2) (Cp' = eta(5)-Me5C5 ; An = Th, R = CH2(SiMe3), 5; An = U, R = CH2(SiMe3), 6) complexes. Complexes 1-6 exhibit broad applicability for the intramolecular hydroamination of diverse C-C unsaturations, including terminal and internal aminoalkenes (primary and secondary amines), aminoalkynes (primary and secondary amines), aminoallenes, and aminodienes. Large turnover frequencies (N-t up to 3000 h(-1)) and high regioselectivities (>= 95%) are observed throughout, along with moderate to high diastereoselectivities (up to 90% trans ring closures). With several noteworthy exceptions, reactivity trends track relative 5f ionic radii and ancillary ligand coordinative unsaturation. Reactivity patterns and activation parameters are consistent with a reaction pathway proceeding via turnover-limiting CC/CC insertion into the An-N sigma-bond.

表征谱图