Lauroyl azide | 43009-32-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Lauroyl azide
• 英文别名: Lauroylazid；Dodecanoylazid；Dodecanoyl azide
• CAS: 43009-32-1
• 化学式: C₁₂H₂₃N₃O
• 分子量: 225.334
• InChiKey: XBIVQDRLEPKWNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Lauroyl azide 在 zinc(II) tetrahydroborate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.5h， 以92%的产率得到月桂酰胺
  参考文献：
  名称：

  Reduction of Azides with Zinc Borohydride

  摘要：

  Zinc borohydride in 1,2-dimethoxyethane provides an efficient procedure for the reduction of organic azides. Aroyl, acyl, and arylsulfonyl azides readily undergo reduction at room temperature to produce amides and sulfonamides in excellent yields; however, substitution with electron-withdrawing groups in the aroyl azides leads to the corresponding benzyl alcohols. Reduction of aryl and alkyl azides has also been achieved in high yields, under some modified conditions.

  DOI：

  10.1021/jo00094a021
• 作为产物：
  描述：

  月桂酰氯 在 sodium azide 作用下， 以 乙醚 为溶剂， 生成 Lauroyl azide
  参考文献：
  名称：

  由链烷酰胺盐和链烷磺酰胺生成腈

  摘要：

  N-三甲基氨基十二烷磺酰胺盐和N-三甲基碘十二烷磺酸盐在非水溶剂中被热解和光解。磺酰胺盐的热分解产生磺酰氮，其被亲核试剂捕获。磺酰胺盐对紫外线辐射稳定。链烷酰胺酸酯通过一致的分子内过程热分解而得到异氰酸十一烷基酯，该过程不涉及形成腈中间体。通过在二甲基亚砜中光解链烷酰胺化生成的十二烷酰基氮烯已与从酰基叠氮化物光解获得的类似腈进行了比较。讨论了氮烯中间体的电子态。

  DOI：

  10.1039/j29680000463

文献信息

• Expanding the gelation properties of valine-based 3,5-diaminobenzoate organogelators with <i>N</i>-alkylurea functionalities
  作者：Hak-Fun Chow、Chin-Ho Cheng

  DOI：10.3762/bjoc.6.114

  日期：——

  A new family of valine-containing 3,5-diaminobenzoate derivatives 2 with N-alkylurea moieties attached to the valine moieties was prepared. By appending these two new N-alkylurea chains to the molecular structure, their organogelating properties were extended from only aromatic solvents, to a wide range of other types of solvents such as alicyclic hydrocarbons, alcohols and polar solvents such as DMSO and DMF. It was also found that a longer N-alkylurea chain conferred improved gelation power and higher thermal stability as compared to those of the shorter ones.

  一种新的含缬氨酸的3,5-二氨基苯甲酸衍生物2，其中缬氨酸基团连接有N-烷基脲基团，已经制备。通过将这两个新的N-烷基脲基链附加到分子结构中，它们的有机凝胶化性质从仅限于芳香溶剂扩展到范围广泛的其他类型的溶剂，如脂环烃、醇类和极性溶剂，如DMSO和DMF。还发现，较长的N-烷基脲基链相比较短链具有更好的凝胶化能力和更高的热稳定性。
• Synthesis of Polymerizable Double-Chain Glycolipids derived from Tris. Polymerization in aqueous Media. Preliminary Investigation of their Colloidal Behavior
  作者：Ange Polidori、Olivier Braun、Nathalie Mora、Bernard Pucci*

  DOI：10.1016/s0040-4039(97)00413-9

  日期：1997.4

  A series of mono and double tailed hydro and perfluorocarbon surfactant derived from Tris(hydroxymethyl)aminomethane and bearing an acryloyl moiety on the hydrophilic head have been prepared. The bicodal surfactants dispersed in water by ultrasonication formed vesicles which precipitated after UV irradiation. We describe a new method to stabilize these vesicular dispersions during the polymerization

  制备了一系列衍生自三（羟甲基）氨基甲烷并在亲水头上带有丙烯酰基部分的单尾和双尾氢和全氟化碳表面活性剂。通过超声处理分散在水中的双水合表面活性剂形成囊泡，该囊泡在紫外线照射后沉淀。我们描述了一种通过添加单壳两亲物来稳定聚合过程中稳定这些水泡分散体的新方法。©1997由Elsevier Science Ltd发布。
• TCT-mediated click chemistry for the synthesis of nitrogen-containing functionalities: conversion of carboxylic acids to carbamides, carbamates, carbamothioates, amides and amines
  作者：Riyaz Ahmed、Ria Gupta、Zaheen Akhter、Mukesh Kumar、Parvinder Pal Singh

  DOI：10.1039/d2ob00324d

  日期：——

  s-trichlorotriazine (TCT, also known as cyanuric chloride) mediated one-pot general method for the conversion of carboxylic acids into ubiquitous functionalities such as carbamides, carbamates, carbamothioates, amides, and amines. The TCT-mediated activation of acids followed by azidation and heating led to the isocyanate formation via Curtius rearrangement which involves click chemistry in the presence of nucleophiles

  在这里，我们报告了一种s-三氯三嗪（TCT，也称为三聚氯氰）介导的一锅通用方法，用于将羧酸转化为普遍存在的官能团，例如尿酰胺、氨基甲酸酯、氨基甲酸酯、酰胺和胺。TCT 介导的酸活化，然后是叠氮化和加热导致异氰酸酯通过Curtius 重排，涉及在亲核试剂存在下的点击化学并提供偶联产物。相对于起始材料，TCT 的使用量≤40 mol%；然而，它的大量可用性和低成本为其在功能分子合成中的适用性提供了独特的机会。优化的条件也已成功地用于克级合成和天然产物和药物（如鬼臼毒素、丁香酚、薯蓣皂苷元、香叶醇和氟伏沙明）的后期功能化。
• Curtius, Journal fur praktische Chemie (Leipzig 1954), 1914, vol. <2> 89, p. 500,512
  作者：Curtius

  DOI：——

  日期：——
• Stabilization of polymerized vesicular systems: an application of the dynamic molecular shape concept
  作者：Michel Wathier、Ange Polidori、Karine Ruiz、Anne-Sylvie Fabiano、Bernard Pucci

  DOI：10.1016/s0009-3084(02)00006-3

  日期：2002.5

  A series of glycolipid surfactants derived from Tris(hydroxymethyl)acrylamidomethane (THAM) and bearing hydrocarbon or perfluorocarbon tails and an acryloyl group attached to their polar head was prepared to explore the aqueous behavior of the supramolecular systems they form. The dispersion Of surfactants was achieved in water under ultrasonication conditions. Hydrocarbon Compounds give heterogeneous vesicular assemblies. In the case of perfluorocarbon derivatives homogeneous vesicles were obtained. However after Way storage, all these systems fuse. To stabilize these vesicles, polymerization by ultra violet (UV) irradiation was carried Out. During this reaction, a precipitation in water was observed for the hydrocarbon surfactants, whereas fluorocarbon Structures provide stable vesicles Without any alteration of their size. According to these results, the polymerization process was achieved, in the case of hydrocarbon glycolipid, in the presence of different cosurfactants bearing a single hydrocarbon tail or a polyhydroxylated head and a cholesterol terminus. In Such conditions, homogeneous stable vesicles were prepared. Moreover, the THAM derived telomers bearing a cholesterol terminus were able to stabilize and reduce the size of vesicles formed with synthetic glycolipid surfactants. The drug encapsulation ability of these systems was investigated by measurement of the release kinetics of a fluorescent dye, carboxyfluorescein (CF), before and after polymerization. (C) 2002 Published by Elsevier Science Ireland Ltd.