Neopentyl azide | 102711-08-0

• 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: Neopentyl azide
• 英文别名: 1-Azido-2,2-dimethylpropane
• CAS: 102711-08-0
• 化学式: C₅H₁₁N₃
• 分子量: 113.162
• InChiKey: TUMDKSIKQMCKBL-UHFFFAOYSA-N

物化性质

• 沸点：
  105-107 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  8
• 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：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异丁酸甲酯 、 Neopentyl azide 在 正丁基锂 、 二异丙胺 作用下， 生成 3-(2,2-Dimethylpropyl)-3,5-dihydro-5,5-dimethyl-4H-1,2,3-triazol-4-on
  参考文献：
  名称：

  Quast, Helmut; Meichsner, Georg; Seiferling, Bernhard, Liebigs Annalen der Chemie, 1986, # 11, p. 1891 - 1899

  摘要：

  DOI：
• 作为产物：
  描述：

  新戊基碘 在 sodium azide 作用下， 以 various solvent(s) 为溶剂， 反应 120.0h， 以67%的产率得到Neopentyl azide
  参考文献：
  名称：

  Quast, Helmut; Meichsner, Georg; Seiferling, Bernhard, Liebigs Annalen der Chemie, 1986, # 11, p. 1891 - 1899

  摘要：

  DOI：

文献信息

• Exploring the Border between Concerted and Two-Step Pathways of 1,3-Dipolar Cycloadditions of Organic Azides to Cyclic Ketene N,X-Acetals. - Synthesis and15N-NMR Spectra of Zwitterions and Spirocyclic Cycloadducts
  作者：Helmut Quast、Manfred Ach、Jürgen Balthasar、Thomas Hergenröther、Dieter Regnat、Jens Lehmann、Klaus Banert

  DOI：10.1002/hlca.200590126

  日期：2005.6

  Cyclic ketene N,X-acetals 1 are electron-rich dipolarophiles that undergo 1,3-dipolar cycloaddition reactions with organic azides 2 ranging from alkyl to strongly electron-deficient azides, e.g., picryl azide (2L; R1=2,4,6-(NO2)3C6H2) and sulfonyl azides 2M–O (R1=XSO2; cf. Scheme 1). Reactions of the latter with the most-nucleophilic ketene N,N-acetals 1A provided the first examples for two-step H

  环烯酮N，X-乙缩醛1是富含电子的双亲亲子，与有机叠氮化物2发生1,3-偶极环加成反应，有机叠氮化物2的烷基化程度强至电子缺乏性叠氮化物，例如吡啶甲基叠氮化物（2L ; R 1 = 2,4， 6-（NO 2）3 C 6 H 2）和磺酰叠氮化物2M – O（R 1 = XSO 2；参见方案1）。后者与亲核性最强的乙烯酮N，N-缩醛1A的反应提供了一种用于两步骤HOMO（亲偶极）-LUMO（1,3-偶极子）的第一实施例-controlled 1,3-偶极环加成经由中间两性离子3。为了为探索这种类型的协同步骤和两步式1,3-偶极环加成之间的边界奠定基础，我们首先描述了2到1的协同环加成的范围和局限性，并描述了两性离子3。烷基叠氮化物2A – C仅添加到由1 H-四唑（参见1A）和1 H-咪唑（参见1B，C）衍生的乙烯酮N，N-缩醛中），而几乎所有的芳基叠氮化物都使用烯酮N，X-乙缩醛（X = NR，O，S）生成环加合物4，但1
• The effects of ionic liquids on azide-alkyne cycloaddition reactions
  作者：Stephen R. D. George、Gavin L. Edwards、Jason B. Harper

  DOI：10.1039/c0ob00306a

  日期：——

  The effect of a series of ionic liquids on the regioselectivity of the azide-alkyne cycloaddition process was investigated, demonstrating an increased selectivity for the least hindered triazole. The effects of an ionic liquid on the activation parameters for the process were determined and found to be intermediate between coordinating and non-coordinating salts. The importance of knowing the water content of the system is demonstrated by marked changes in the activation parameters in the presence of small concentrations of water.

  研究了一系列离子液体对叠氮-炔环化反应过程的区域选择性的影响，结果表明受阻最小的三唑的选择性增加。测定了离子液体对该过程活化参数的影响，发现其介于配位盐和非配位盐之间。在存在小浓度水的情况下，活化参数会发生明显变化，这表明了解体系中水含量的重要性。
• Synthesis and biological evaluation of triazole analogues of antillatoxin
  作者：Ryosuke Goto、Ken Okura、Hayato Sakazaki、Tatsuya Sugawara、Shigeru Matsuoka、Masayuki Inoue

  DOI：10.1016/j.tet.2011.05.012

  日期：2011.9

  Antillatoxin 1, a cyclic lipopeptide, is known as an activator of voltage-gated sodium channels and exhibits potent neurotoxicity toward Neuro 2a mouse neuroblastoma cells. To investigate the biological effects of the side-chain structures at C5 and C5' in detail, we planned SAR studies of C5- and C5'-modified antillatoxin analogues. To diversify the structures at the last step of the synthesis, two key intermediates 4 and 6 possessing terminal alkynes at the C5- and C5'-positions were designed and synthesized using two distinct strategies. Sixteen side-chain derivatives were then prepared from 4 and 6 by coupling with a wide variety of azides via click chemistry, and subjected to the cytotoxicity assay. Although almost all of the C5-substituted analogues exhibited no cytotoxicity, the C5'-substituted analogues showed modest cytotoxicity. These results showed that C5' is more tolerant than C5 to structural modifications. The present SAR study will provide valuable information for designing new antillatoxin-based molecular probes for neuroscience research. (C) 2011 Elsevier Ltd. All rights reserved.
• Quast, Helmut; Bieber, Lothar; Meichsner, Georg, Liebigs Annalen der Chemie, 1987, p. 469 - 476
  作者：Quast, Helmut、Bieber, Lothar、Meichsner, Georg

  DOI：——

  日期：——
• Ponomarchuk, M. P.; Sologub, L. S.; Kasukhin, L. F., Journal of general chemistry of the USSR, 1985, vol. 55, # 8, p. 1532 - 1536
  作者：Ponomarchuk, M. P.、Sologub, L. S.、Kasukhin, L. F.、Kukhar', V. P.

  DOI：——

  日期：——