1-azido-4-iodobutane | 148759-55-1

• 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: 1-azido-4-iodobutane
• CAS: 148759-55-1
• 化学式: C₄H₈IN₃
• 分子量: 225.032
• InChiKey: QVZUACRCBPIEKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1-脱氧野尻霉素 、 1-azido-4-iodobutane 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Exploring substituent diversity of deoxynojirimycin–triazole hybrid iminosugars: Discovery of potent glucosidase inhibitors

  摘要：

  A series of deoxynojirimycin-triazole hybrid iminosugars had been prepared and investigated against a panel of glucosidases. Compound 10f (IC50 = 0.063 +/- 0.006 mM) exhibited improved inhibitory potency against alpha-glucosidase compared to 1-deoxynojirimycin (IC50 = 0.155 +/- 0.015 mM). Moreover, analysis of the kinetics of enzyme inhibition by using Lineweaver-Burk plots indicated that 10f inhibited alpha-glucosidase in a competitive manner. Compound 10m displayed moderate inhibition of alpha-glucosidase and beta-glucosidase. The structure-activity relationships indicated that the introduction of the phenyl group and the nature of 4-position substituents on the phenyl ring had significant effects on the glucosidase inhibitory potency of the compounds.

  DOI：

  10.1080/07328303.2020.1837150
• 作为产物：
  描述：

  1-溴-4-氯丁烷 在 sodium azide 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 44.0h， 以78%的产率得到1-azido-4-iodobutane
  参考文献：
  名称：

  Fluorination Triggers Fluoroalkylation: Nucleophilic Perfluoro‐ tert ‐butylation with 1,1‐Dibromo‐2,2‐bis(trifluoromethyl)ethylene (DBBF) and CsF

  摘要：

  AbstractPerfluoro‐tert‐butylation reaction has long remained a challenging task. We now report the use of 1,1‐dibromo‐2,2‐bis(trifluoromethyl)ethylene (DBBF) as a practical reagent for perfluoro‐tert‐butylation reactions for the first time. Through a consecutive triple‐fluorination process with DBBF and CsF, the (CF3)3C− species can be liberated and observed, which is able to serve as a robust nucleophilic perfluoro‐tert‐butylating agent for various electrophiles. The power of this synthetic protocol is evidenced by the efficient synthesis of structurally diverse perfluoro‐tert‐butylated molecules. Multiple applications demonstrate the practicability of this method, as well as the superiority of perfluoro‐tert‐butylated compounds as sensitive probes. The perfluoro‐tert‐butylated product was successfully applied in 1H‐ and 19F‐magnetic resonance imaging (MRI) experiment with an ultra‐low field (ULF) MRI system.

  DOI：

  10.1002/anie.202113727

文献信息

• Highly Substituted Δ ³ ‐1,2,3‐Triazolines: Solid‐State Emitters with Electrofluorochromic Behavior
  作者：Abdusalom A. Suleymanov、Albert Ruggi、Ophélie Marie Planes、Anne‐Sophie Chauvin、Rosario Scopelliti、Farzaneh Fadaei Tirani、Andrzej Sienkiewicz、Alberto Fabrizio、Clémence Corminboeuf、Kay Severin

  DOI：10.1002/chem.201901345

  日期：2019.5.10

  substituted Δ3‐1,2,3‐triazolines can be prepared by reaction of triarylvinyl Grignard reagents with functionalized organic azides. The heterocycles are fluorescent in the solid state, and—depending on the substituents—they can display aggregation‐induced emission. Upon oxidation, the triazolines form stable radical cations with altered photophysical properties. Therefore, they represent rare examples of

  高度取代的Δ 3 -1,2,3- triazolines可以通过用官能化有机叠氮化物triarylvinyl格氏试剂的反应来制备。杂环在固态时是发荧光的，并且取决于取代基，它们可以显示聚集诱导的发射。在氧化时，三唑啉形成具有改变的光物理性质的稳定的自由基阳离子。因此，它们代表了具有内在电致变色行为的固态发射器的罕见示例。
• One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides
  作者：Abdusalom A. Suleymanov、Rosario Scopelliti、Farzaneh Fadaei Tirani、Kay Severin

  DOI：10.1021/acs.orglett.8b01214

  日期：2018.6.1

  and versatile method for the preparation of linear, trisubstituted triazenes is reported. The procedure is based on the reaction of Grignard reagents with 1-azido-4-iodobutane or 4-azidobutyl-4-methylbenzenesulfonate. These organic azides enable the regioselective formation of triazenes via an intramolecular cyclization step. The new method can be used for the preparation of aryl, heteroaryl, vinyl,

  报道了一种简单且通用的制备线性三取代的三氮烯的方法。该程序基于格氏试剂与1-叠氮基-4-碘丁烷或4-叠氮基丁基-4-甲基苯磺酸的反应。这些有机叠氮化物能够通过分子内环化步骤在区域上选择性地形成三氮烯。该新方法可用于制备芳基，杂芳基，乙烯基和烷基三氮烯。酸诱导的C–N，C–O，C–F，C–P和C–S键形成反应证明了乙烯基三氮烯的合成效用。
• A Common Diaryl Ether Intermediate for the Gram-Scale Synthesis of Oxazine and Xanthene Fluorophores
  作者：Andrew V. Anzalone、Tracy Y. Wang、Zhixing Chen、Virginia W. Cornish

  DOI：10.1002/anie.201205369

  日期：2013.1.7

  Common ground: Copper‐catalyzed coupling reactions can be used for the high‐yielding preparation of widely used oxazine and xanthene fluorophores from a common diaryl ether intermediate on a gram‐scale (see scheme). This general approach may facilitate the future development of novel fluorophores and probes with unique properties.

  共同点：铜催化的偶联反应可用于从常见的二芳基醚中间体以克级规模制备广泛使用的恶嗪和呫吨荧光团（参见方案）。这种通用方法可能有助于未来开发具有独特性质的新型荧光团和探针。
• Gold-Catalyzed Highly Regioselective Oxidation of C−C Triple Bonds without Acid Additives: Propargyl Moieties as Masked α,β-Unsaturated Carbonyls
  作者：Biao Lu、Chaoqun Li、Liming Zhang

  DOI：10.1021/ja1072614

  日期：2010.10.13

  Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylquinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile α,β-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A range of functional groups such as THP, MOMO, N(3), OTBS, and N-Boc are tolerated

  使用 8-烷基喹啉 N-氧化物作为氧化剂并且在没有酸添加剂的情况下，已经以高区域选择性实现了内部炔烃的金催化分子间氧化。合成通用的 α,β-不饱和羰基化合物以良好到极好的收率和极好的 E 选择性获得。可以容忍一系列功能组，例如 THP、MOMO、N(3)、OTBS 和 N-Boc。该反应允许 α,β-不饱和羰基被掩蔽为炔丙基部分，从而为复杂结构合成中可能遇到的这些官能团的相容性问题提供了实用的解决方案。
• 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。