4-十六烷基-1,2,4-三唑 | 188113-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-十六烷基-1,2,4-三唑
• 英文名称: 4-hexadecyl-1,2,4-triazole
• 英文别名: 4-Hexadecyl-4H-1,2,4-triazole
• CAS: 188113-56-6
• 化学式: C₁₈H₃₅N₃
• 分子量: 293.496
• InChiKey: FISOZNHIGUOENB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-十六烷基-1,2,4-三唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以31%的产率得到3,5-dibromo-4-hexadecyl-1,2,4-triazole
  参考文献：
  名称：

  新型以噻吩为基础的交替π-共轭共聚物的合成，固体结构和光学性质，该共聚物包含4-烷基-1,2,4-三唑或1,3,4-噻二唑单元作为伙伴单元

  摘要：

  DOI：

  10.1021/ma0488820
• 作为产物：
  描述：

  十六胺 、 N,N-dimethylformamide azine dihydrochloride 以 吡啶 为溶剂， 以70%的产率得到4-十六烷基-1,2,4-三唑
  参考文献：
  名称：

  Effect of N⁴-Substituent Choice on Spin Crossover in Dinuclear Iron(II) Complexes of Bis-Terdentate 1,2,4-Triazole-Based Ligands

  摘要：

  Seven new dinuclear iron(II) complexes of the general formula [Fe-2(II)(PMKT)(2)] (BF4)(4)center dot solvent, where PMRT is a 4-substituted-3,5-bis{[(2-pyridylmethyl)-amino]methyl}-4H-1,2,4-triazole, have been prepared in order to investigate the substituent effect on the spin crossover event. Variable temperature magnetic susceptibility and Fe-57 Mossbauer spectroscopy studies show that two of the complexes, [Fe-2(II)(PMPT)(2)](BF4)(4)center dot H2O (N-4 substituent is pyrrolyl) and [Fe-2(II)(PM(Ph)AT)(2)](BF4)(4) (N-4 is N,N-diphenylamine), are stabilized in the [HS-HS] state between 300 and 2 K with weak antiferromagnetic interactions between the iron(II) centers. Five of the complexes showed gradual half spin crossover, from [HS-HS] to [HS-LS], with the following, T-1/2 (K) values: 234 for [Fe-2(II)(PMibT)(2)](BF4)(4)center dot 3H(2)O (N-4 is isobutyl), 147 for [Fe-2(II)(PMBzT)(2)](BF4)(4) (N-4 is benzyl), 133 for [Fe-2(II)((PMPhT)-Ph-CF3)(2)](BF4)(4)center dot DMF center dot H2O (N-4 is 3,5-bis(trifluoromethyl)phenyl), 187 for [Fe-2(II)(PMPhT)(2)](BF4)(4) (N-4 is phenyl), and 224 for [Fe-2(II)(PMC16T)(2)](BF4)(4) (N-4 is hexadecyl). Structure, determinations carried out for three complexes, [Fe-2(II)(PMPT)2](BF4)(4)center dot 4DMF, [Fe-2(II)(PMBzT)(2)](BF4)(4)center dot CH3CN, and [Fe-2(II)(PM(Ph)AT)(2)](BF4)(4)center dot solvent, revealed that in all three complexes both iron(II) centers are stabilized in the high spin state at 90 K. A general and reliable 4-step route to PMRT ligands is also detailed.

  DOI：

  10.1021/ic4014416

文献信息

• Spin-transition behaviour in chains of FeII bridged by 4-substituted 1,2,4-triazoles carrying alkyl tails
  作者：Olivier Roubeau、Jose´ M. Alcazar Gomez、Emily Balskus、Jeroen J. A. Kolnaar、Jaap G. Haasnoot、Jan Reedijk

  DOI：10.1039/b007094g

  日期：——

  A family of polymeric 1-dimensional chains of iron(II) species showing the spin-crossover phenomenon has been synthesized using 4-n-alkyl-1,2,4-triazoles as bridging ligands. The influence of the length of the alkyl tails on the triazole ligands on characteristic features of the spin transition was studied, showing degrading of steepness with increasing length. A set of four counter ions has been used to access a wider range of transition temperatures. Large hysteresis loops are detected with small tails, mainly for the methyl and ethyl substituted products. In most cases longer tails weaken co-operativity and hysteresis gradually decreases to zero. However it is shown that with certain anions hysteresis remains, even with very long tails on the triazoles. Weakening of the co-operativity mainly arises from a diminution of the length of the polymeric chains with increasing alkyl tails on the triazole. This effect is anion dependent. A strong interaction along the polymeric chains is confirmed.

  合成了一种聚合物一维链的铁(II)物种，表现出自旋跨越现象，采用4-n-烷基-1,2,4-三唑作为桥联配体。研究了烷基尾巴长度对三唑配体自旋跃迁特征的影响，发现随着烷基尾巴长度的增加，自旋跃迁的陡峭度降低。使用了一组四种对离子，以获取更广泛的跃迁温度范围。检测到小尾巴的样品存在较大的滞回环，主要是甲基和乙基取代的产物。在大多数情况下，较长的尾巴削弱了协同作用，滞回现象逐渐减小至零。然而，研究表明，对于某些阴离子，即使在三唑上有很长的尾巴，滞回现象仍然存在。协同作用的减弱主要源于随着三唑上的烷基尾巴增大，聚合物链的长度减少。这个效应依赖于阴离子。确认了聚合物链之间存在强相互作用。
• Tetranuclear Silver(I) Clusters Showing High Ionic Conductivity in a Bicontinuous Cubic Mesophase
  作者：Padi Y. S. Su、Jing C. W. Tseng、Kwang-Ming Lee、Ju-Chun Wang、Ivan J. B. Lin

  DOI：10.1021/ic500627d

  日期：2014.6.16

  CnH2n+1 with n = 12, 14, 16, and 18), are reported. Upon heating, a phase transition sequence of Cr → SmC → Cub → SmA → isotropic liquid is observed for all of these compounds. Depending on the alkyl chain length, two types of cubic phases are found in this series of compounds. Those with shorter alkyl chains (n = 12 and 14) exhibit a micellar cubic phase, whereas long alkyl chains (n =16 and 18) show

  四核三唑银金属致孔菌，[Ag 4（L 4 -C n）6 ] [BF 4 ] 4（L 4 -C n = 4-烷基-1,2,4-三唑，其中C n代表据报道C n H 2 n +1，其中n＝ 12、14、16和18。加热后，观察到所有这些化合物的Cr→SmC→Cub→SmA→各向同性液体的相变顺序。根据烷基链的长度，在这一系列化合物中发现了两种类型的立方相。那些具有较短的烷基链（Ñ= 12和14）呈现胶束立方相，而长烷基链（n = 16和18）显示双连续立方相。由于存在三维离子传输通道，在[Ag 4（L 4 -C 16）6 ] [BF 4 ] 4的双连续立方中间相上观察到了优异的离子电导率。掺杂少量的AgBF 4可能会通过促进通道中Ag I离子的迁移而显着增强离子传导。
• Heat-Set Gel-like Networks of Lipophilic Co(II) Triazole Complexes in Organic Media and Their Thermochromic Structural Transitions
  作者：Keita Kuroiwa、Tomoko Shibata、Akihiko Takada、Norio Nemoto、Nobuo Kimizuka

  DOI：10.1021/ja037847q

  日期：2004.2.1

  These observations indicate that T(d) complexes are present as low-molecular weight species around at 25-27 degrees C. They are self-assembled to polymeric T(d) complexes by heating and form gel-like networks. Upon cooling the solution below 25 degrees C, T(d) complexes are converted to O(h) complexes and they also self-assemble into oligomeric or polymeric species at lower temperatures. The observed

  一类新型的热响应超分子组装体由 4-烷基化 1,2,4-三唑的亲脂性钴 (II) 配合物形成。当在烷基链部分中引入醚键时，即使在非常低的浓度（室温下约 0.01 重量％）中，也会在氯仿中形成蓝色凝胶状相。蓝色伴随着 580-730 nm 附近的结构化吸收，这是四面体 (T(d)) 配位中钴 (II) 的特征。凝胶状相的原子力显微镜 (AFM) 和透射电子显微镜 (TEM) 证实了宽度为 5-30 nm 的纤维纳米组件网络的形成。观察到的宽度大于三唑配体的分子长度 (ca. 2.2 nm)，它们由 T(d) 配位聚合物的聚集体组成。非常有趣的是，蓝色凝胶状相通过冷却到 25 摄氏度以下变成溶液。在 0 摄氏度时获得淡粉色溶液，表明形成了八面体 (O(h)) 配合物。观察到的热致变色转变是完全可逆的。通过加热形成凝胶状网络与加热时溶解的常规有机凝胶相反。存储和损耗模量（G' 和 G"）的温度依赖性在
• Abenhaim, David; Diez-Barra, Enrique; Hoz, Antonio de la, Heterocycles, 1994, vol. 38, # 4, p. 793 - 802
  作者：Abenhaim, David、Diez-Barra, Enrique、Hoz, Antonio de la、Loupy, Andre、Sanchez-Migallon, Ana

  DOI：——

  日期：——
• Liquid-Crystalline Zinc(II) and Iron(II) Alkyltriazoles One-Dimensional Coordination Polymers
  作者：Pauline Grondin、Diana Siretanu、Olivier Roubeau、Marie-France Achard、Rodolphe Clérac

  DOI：10.1021/ic300404r

  日期：2012.5.7

  Several series of unidimensional coordination polymers of formula [Zn(C(5)H(2n+1)trz)(3)](Cl)(2)center dot xH(2)O (n = 18, 16, 13, 11, 10, trz = 4-substituted-1,2,4-triazole), [Zn(C(18)H(37)trz)(3)](ptol)(2)center dot xH(2)O, [Fe(C(n)H(2n+1)trz)(3)](X)(2)center dot xH(2)O (n = 18, 16, 13, 10; X = Cl- or ptol(-), where ptol(-) = p-tolylsulfonate anion), and [Fe(C(18)H(37)trz)(3)](X)(2)center dot xH(2)O (X = C8H17PhSO3- and C8H17SO3-) are reported with their thermal, structural, and magnetic properties. Most of these materials exhibit thermotropic lamellar mesophases at temperatures as low as 410 K, as confirmed by textures observed by polarized optical microscopy. The corresponding phase diagrams deduced by differential scanning calorimetry are also reported. All iron-containing materials present a spin crossover phenomenon that occurs at temperatures ranging from 242 to 360 K, only slightly below the mesophase temperature domain, and remains complete and cooperative, even for the longer alkyl substituents. The use of stable diamagnetic Zn(II) analogues proves to be very useful to characterize the comparatively less stable and less crystalline Fe(II) analogues.