N-azidomethyl-N,N-dimethylamine | 88394-66-5

• 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: N-azidomethyl-N,N-dimethylamine
• 英文别名: azidomethyl-dimethyl-amine；1-azido-N,N-dimethylmethanamine
• CAS: 88394-66-5
• 化学式: C₃H₈N₄
• 分子量: 100.123
• InChiKey: WVJADHORXWQFRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  17.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-azidomethyl-N,N-dimethylamine 在 盐酸 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 生成 diazidomethane
  参考文献：
  名称：

  Synthesis of azidochloromethane and azidobromomethane

  摘要：

  By treatment of tris(azidomethyl)amine with dry hydrogen halide, azidochloromethane and azidobromomethane were prepared. The former product, which is more stable than the latter, was isolated as a colorless liquid. The desired azidohalomethanes are intermediates in the nucleophilic substitution of dihalomethanes to generate diazidomethane but could not be detected in this transformation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.094
• 作为产物：
  描述：

  1-甲氧基-N,N-二甲基甲胺 在 叠氮基三甲基硅烷 作用下， 生成 N-azidomethyl-N,N-dimethylamine
  参考文献：
  名称：

  Molecular Structure of N-azidomethyl-N,N-dimethylamine According to Gas-phase Electron Diffraction Data and Quantum-chemical Calculations

  摘要：

  As found experimentally (gas-phase electron diffraction) and theoretically, the equilibrium conformers of N-azidomethyl-N,N-dimethylamine are stabilized by anomeric effects.

  DOI：

  10.1016/j.mencom.2013.05.016

文献信息

• 一类藤黄属三氮唑衍生物、其制备方法和医药 用途
  申请人：中国药科大学

  公开号：CN104447786B

  公开（公告）日：2016-08-24

  本发明涉及药物化学领域，具体涉及一类藤黄属三氮唑衍生物(I)、其制备方法和在制药中的应用，其中R1、R2、n的定义同说明书。该衍生物是藤黄属天然产物藤黄酸的结构类似物，具有抗肿瘤作用，可用于制备抗肿瘤药物。
• Hydrazoic acid in the Mannich reaction
  作者：A. N. Gafarov

  DOI：10.1007/s11172-009-0296-8

  日期：2009.10

  The possibility of the three-component condensation of hydrazoic acid and formaldehyde with primary or secondary amines, as well as with trialkylhydrazines, leading to the corresponding N-azidomethyl derivatives of amines and hydrazides was established.

  确定了重氮酸和甲醛与伯胺或仲胺以及三烷基肼的三组分缩合的可能性，从而产生相应的胺和酰肼的 N-叠氮甲基衍生物。
• Too Short-Lived or Not Existing Species:<i>N</i>-Azidoamines Reinvestigated
  作者：Klaus Banert、Tom Pester

  DOI：10.1021/acs.joc.9b00034

  日期：2019.4.5

  Treatment of N-chlorodimethylamine with sodium azide in dichloromethane does not lead to N-azidodimethylamine, as thought for more than 50 years. Instead, surprisingly, (azidomethyl)dimethylamine is generated with good reproducibility. A plausible reaction mechanism to explain the formation of this product is presented. The reaction of lithium dibenzylhydrazide with tosyl azide does not result in the

  如50多年来所认为的那样，用叠氮化钠在二氯甲烷中处理N-氯二甲基胺不会导致N-叠氮基二甲基胺。相反，令人惊讶地，产生了具有良好再现性的（叠氮甲基）二甲基胺。提出了一个合理的反应机理来解释该产物的形成。如前所述，二苄基肼基锂与甲苯磺酰基叠氮化物的反应不会导致生成N-叠氮基胺，可以通过IR光谱法在环境温度下对其进行检测。重氮基转移至酰肼锂的其他实验表明，中间体N-叠氮基胺的寿命很短，或者通过同步断裂两个N-N键直接生成1,1-二氮烯来绕开它们的形成。
• Direct N-alkyl azidonation of N,N-dialkylarylamines with the iodosylbenzene/trimethylsilyl azide reagent combination
  作者：Philip Magnus、Jerome Lacour、Wolfgang Weber

  DOI：10.1021/ja00073a084

  日期：1993.10
• Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations
  作者：Orudzh G. Nabiev、Zargalam O. Nabizade、Remir G. Kostyanovsky

  DOI：10.1016/j.mencom.2009.09.018

  日期：2009.9

  Simple and efficient methods have been developed to obtain cyanomethylamines and azidomethylamines using reactions of methoxymethylamines with TMSCN and TMSN3, respectively. In the case of dimethylformamide dimethylacetal, only one MeO group was substituted with CN, and an unexpected direction of the subsequent azidation was found. Adducts of azidomethylamines with DMAD were studied, and the base-catalyzed isomerization of symmetric triazoles into non-symmetric ones was revealed.