6-azidohexane-1-thiol | 1025491-16-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-azidohexane-1-thiol
• 英文别名: 6-Azidohexane-1-thiol
• CAS: 1025491-16-0
• 化学式: C₆H₁₃N₃S
• 分子量: 159.255
• InChiKey: CJIONPBRLHKTGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-azidohexane-1-thiol 在 碘 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 1,2-bis(6-azidohexyl)disulfane
  参考文献：
  名称：

  单纳米粒子级的等离子体共振散射光谱：点击反应的实时监控

  摘要：

  建立了基于等离振子共振瑞利散射（PRRS）光谱和暗场显微镜（DFM）的方法，用于在单纳米颗粒水平上实时监测点击反应。点击的单个的金纳米颗粒（的GNP）结果在颗粒间的耦合，在表面上的反应，这导致所述的红移λ最大（Δ λ最大值在PRRS光谱= 43纳米），并在单个的金纳米颗粒的颜色变化DFM（从绿色到橙色）。

  DOI：

  10.1002/anie.201301930
• 作为产物：
  描述：

  6-叠氮基-1-己醇 在 硫脲 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 22.41h， 生成 6-azidohexane-1-thiol
  参考文献：
  名称：

  Reactions in Elastomeric Nanoreactors Reveal the Role of Force on the Kinetics of the Huisgen Reaction on Surfaces

  摘要：

  The force dependence of the copper-free Huisgen cycloaddition between an alkyne and a surface-bound azide was examined in elastomeric nanoreactors. These studies revealed that pressure and chain length are critical factors that determine the reaction rate. These experiments demonstrate the central role of pressure and surface structure on interfacial processes that are increasingly important in biology, materials science, and nanotechnology.

  DOI：

  10.1021/ja504137u

文献信息

• A click-based modular approach to introduction of peroxides onto molecules and nanostructures
  作者：Alissa Horn、Patrick H. Dussault

  DOI：10.1039/d0ra09088c

  日期：——

  Copper-promoted azide/alkyne cycloadditions (CuAAC) are explored as a tool for modular introduction of peroxides onto molecules and nanomaterials. Dialkyl peroxide-substituted alkynes undergo Cu(I)-promoted reaction with azides in either organic or biphasic media to furnish peroxide-substituted 1,2,3-triazoles. Heterolytic fragmentation of the peroxide to an aldehyde, a side reaction that appears to

  铜促进的叠氮化物/炔烃环加成 (CuAAC) 被探索为一种将过氧化物模块化引入分子和纳米材料的工具。二烷基过氧化物取代的炔烃经历 Cu( I)-在有机或双相介质中促进与叠氮化物的反应，以提供过氧化物取代的 1,2,3-三唑。可以通过使用过量的炔烃、三乙基硅烷的存在或通过使用碘代炔烃底物来抑制过氧化物杂分解成醛，该副反应似乎与三唑的形成有关。简单炔烃与叠氮基取代过氧化物的互补反应效率要低得多。还报道了炔基过氧缩醛的点击反应；可以通过增加过氧缩醛和炔烃之间的距离来最小化还原性碎裂。该策略能够将二烷基过氧化物和过氧缩醛模块化引入金纳米粒子，这是第一个被报道的此类过程。
• Selective inhibition of β-N-acetylhexosaminidases by thioglycosyl–naphthalimide hybrid molecules
  作者：Wei Chen、Shengqiang Shen、Lili Dong、Jianjun Zhang、Qing Yang

  DOI：10.1016/j.bmc.2017.11.042

  日期：2018.1

  To develop selective inhibitors for beta-N-acetylhexosaminidases which are involved in a myriad of physiological processes, a series of novel thioglycosyl-naphthalimide hybrid inhibitors were designed, synthesized and evaluated for inhibition activity against glycosyl hydrolase family 20 and 84 (GH20 and GH84) beta-N-acetylhexosaminidases. These compounds which incorporate groups with varied sizes and lengths at the linker region between thioglycosyl moiety and naphthalimide moiety are designed to improve the selectivity and stacking interactions. The GH84 human O-GlcNAcase (hOGA) was sensitive to the subtle changes in the linker region and the optimal choice is a small size linker with six atoms length. And the GH20 insect beta-N-acetylhexosaminidase OfHex1 could tolerate compounds with a hydrophobic bulky linker. Especially, the compound 5c (hOGA, K-i = 3.46 mu M; OfHex1, K-i > 200 mu M) and the compound 6f (hOGA, K-i > 200 mu M; OfHex1, K-i = 21.81 mu M) displayed high selectivity. The molecular docking results indicated that the inhibition mechanism was different between the two families due to their different structural characteristics beyond the active sites. These results provide some promising clues to improve selectivity of potent molecules against beta-N-acetylhexosaminidases. (C) 2017 Elsevier Ltd. All rights reserved.
• Reactions in Elastomeric Nanoreactors Reveal the Role of Force on the Kinetics of the Huisgen Reaction on Surfaces
  作者：Xu Han、Shudan Bian、Yong Liang、K. N. Houk、Adam B. Braunschweig

  DOI：10.1021/ja504137u

  日期：2014.7.30

  The force dependence of the copper-free Huisgen cycloaddition between an alkyne and a surface-bound azide was examined in elastomeric nanoreactors. These studies revealed that pressure and chain length are critical factors that determine the reaction rate. These experiments demonstrate the central role of pressure and surface structure on interfacial processes that are increasingly important in biology, materials science, and nanotechnology.
• Plasmon Resonance Scattering Spectroscopy at the Single-Nanoparticle Level: Real-Time Monitoring of a Click Reaction
  作者：Lei Shi、Chao Jing、Wei Ma、Da-Wei Li、Jonathan E. Halls、Frank Marken、Yi-Tao Long

  DOI：10.1002/anie.201301930

  日期：2013.6.3

  A method based on plasmon resonance Rayleigh scattering (PRRS) spectroscopy and dark‐field microscopy (DFM) was established for the real‐time monitoring of a click reaction at the single‐nanoparticle level. Click reactions on the surface of single gold nanoparticles (GNPs) result in interparticle coupling, which leads to a red‐shift of the λmax (Δλmax=43 nm) in the PRRS spectra and a color change of

  建立了基于等离振子共振瑞利散射（PRRS）光谱和暗场显微镜（DFM）的方法，用于在单纳米颗粒水平上实时监测点击反应。点击的单个的金纳米颗粒（的GNP）结果在颗粒间的耦合，在表面上的反应，这导致所述的红移λ最大（Δ λ最大值在PRRS光谱= 43纳米），并在单个的金纳米颗粒的颜色变化DFM（从绿色到橙色）。