1-heptyl-1,2,4-triazole | 490024-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-heptyl-1,2,4-triazole
• 英文别名: 1-heptyl-1H-[1,2,4]triazole；n-Hexyl-1-triazol-1,2,4
• CAS: 490024-64-1
• 化学式: C₉H₁₇N₃
• 分子量: 167.254
• InChiKey: XZNJLMMVBHGQGS-UHFFFAOYSA-N

物化性质

• 沸点：
  272.6±23.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  1-heptyl-1,2,4-triazole 以 水 为溶剂， 反应 52.0h， 生成 1-heptyl-4-(1-fluoroethyl)-1,2,4-triazolium bis(trifluoromethanesulfonyl)amide
  参考文献：
  名称：

  Syntheses of 1-Alkyl-1,2,4-triazoles and the Formation of Quaternary 1-Alkyl-4-polyfluoroalkyl-1,2,4-triazolium Salts Leading to Ionic Liquids

  摘要：

  1,2,4-Triazole was alkylated (alkyl = methyl, butyl, heptyl, decyl) at N-1 in > 90% isolated yields. The resulting 1-alkyl triazoles were quaternized at N-4 in > 98% isolated yields using fluorinated alkyl halides with > 98% isolated yields, under neat reaction conditions at 100-120 degreesC to form N1-CH2-N4-(CH2)(2)CmF2m (divided by 1)-triazolium (Taz) iodide (m = 1, 6), N1-C4H9-N4-(CH2)(2)CmF2m (+ 1)-Taz iodide (m = 1, 4, 6), N1-C7H15-N4-(CH2)(2)CmF2m + 1-Taz iodide (m = 1, 4, 6), NI-C10H21-N4-(CH2)(2)CmF2m (+ 1)-Taz iodide (m = 1, 4), and N1-CnH2n (divided by 1)-N4-(CH2)(2)F-Taz bromide (n = 4, 7, 10). Single-crystal X-ray analyses confirmed the structure of [1-CH3-4-CH2CH2CF3-Taz]I-+(-). It crystallized in the orthorhombic space group Pccn, and the unit cell dimensions were a = 13.8289(9) Angstrom, b = 17.3603-(11) Angstrom, c = 9.0587(6) Angstrom (alpha = beta = gamma = 90degrees). Metathesis of these polyfluoroalkyl-substituted triazolium halides with other salts led to the formation of quaternary compounds, some of which comprise ionic liquids, namely, [R(R-f)-Taz]Y-divided by(-) (Y = NTf2, BF4, PF6, and OTf), in good isolated yields without the need for further purification: N1-CH3-N4-(CH2)(2)CmF2m (+) (1)-Taz Y (m = 1, 6; Y = NTf2), N1-C4H9-N4-(CH2)(2)CmF2m (divided by) (1)-Taz Y (m = 1, 4, 6; Y = NTf2), N1-C7H15-N4-(CH2)(2)CmF2m (+ 1)-Taz Y (m = 1, 4, 6; Y = NTf2), N1-C10H21-N4-(CH2)(2)CmF2m (+ 1)-Taz Y (n = 1, 4; Y = NTf2), N1-CnH2n (+ 1)-N4-(CH2)(2)F-Taz Y (n = 7, 10; Y = NTf2), N1-C10H21-N4-(CH2)(2)F-TazY (Y = OTf), N1-C7H15-N4-(CH2)(2)F-TazY (Y = BF4), N1-C4H9-N4-(CH2)(2)C(m)F2(m) (+ 1)-Taz Y (m 4, 6; Y PF6) N1-C7H15-N4-(CH2)(2)C4F9-Taz Y (Y = PF6) N1-C4H9-N4-(CH2)(2)C(m)F2(m) (+ 1)-Taz Y (m 4, 6; Y = OTf). All new compounds were characterized by H-1, F-19, and C-13 NMR and MS spectra and elemental analyses. T(g)s and T(m)s of ionic liquids were determined by DSC.

  DOI：

  10.1021/jo026350g
• 作为产物：
  描述：

  1H-1,2,4-三唑 、 1-碘庚烷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 1-heptyl-1,2,4-triazole
  参考文献：
  名称：

  Syntheses of 1-Alkyl-1,2,4-triazoles and the Formation of Quaternary 1-Alkyl-4-polyfluoroalkyl-1,2,4-triazolium Salts Leading to Ionic Liquids

  摘要：

  1,2,4-Triazole was alkylated (alkyl = methyl, butyl, heptyl, decyl) at N-1 in > 90% isolated yields. The resulting 1-alkyl triazoles were quaternized at N-4 in > 98% isolated yields using fluorinated alkyl halides with > 98% isolated yields, under neat reaction conditions at 100-120 degreesC to form N1-CH2-N4-(CH2)(2)CmF2m (divided by 1)-triazolium (Taz) iodide (m = 1, 6), N1-C4H9-N4-(CH2)(2)CmF2m (+ 1)-Taz iodide (m = 1, 4, 6), N1-C7H15-N4-(CH2)(2)CmF2m + 1-Taz iodide (m = 1, 4, 6), NI-C10H21-N4-(CH2)(2)CmF2m (+ 1)-Taz iodide (m = 1, 4), and N1-CnH2n (divided by 1)-N4-(CH2)(2)F-Taz bromide (n = 4, 7, 10). Single-crystal X-ray analyses confirmed the structure of [1-CH3-4-CH2CH2CF3-Taz]I-+(-). It crystallized in the orthorhombic space group Pccn, and the unit cell dimensions were a = 13.8289(9) Angstrom, b = 17.3603-(11) Angstrom, c = 9.0587(6) Angstrom (alpha = beta = gamma = 90degrees). Metathesis of these polyfluoroalkyl-substituted triazolium halides with other salts led to the formation of quaternary compounds, some of which comprise ionic liquids, namely, [R(R-f)-Taz]Y-divided by(-) (Y = NTf2, BF4, PF6, and OTf), in good isolated yields without the need for further purification: N1-CH3-N4-(CH2)(2)CmF2m (+) (1)-Taz Y (m = 1, 6; Y = NTf2), N1-C4H9-N4-(CH2)(2)CmF2m (divided by) (1)-Taz Y (m = 1, 4, 6; Y = NTf2), N1-C7H15-N4-(CH2)(2)CmF2m (+ 1)-Taz Y (m = 1, 4, 6; Y = NTf2), N1-C10H21-N4-(CH2)(2)CmF2m (+ 1)-Taz Y (n = 1, 4; Y = NTf2), N1-CnH2n (+ 1)-N4-(CH2)(2)F-Taz Y (n = 7, 10; Y = NTf2), N1-C10H21-N4-(CH2)(2)F-TazY (Y = OTf), N1-C7H15-N4-(CH2)(2)F-TazY (Y = BF4), N1-C4H9-N4-(CH2)(2)C(m)F2(m) (+ 1)-Taz Y (m 4, 6; Y PF6) N1-C7H15-N4-(CH2)(2)C4F9-Taz Y (Y = PF6) N1-C4H9-N4-(CH2)(2)C(m)F2(m) (+ 1)-Taz Y (m 4, 6; Y = OTf). All new compounds were characterized by H-1, F-19, and C-13 NMR and MS spectra and elemental analyses. T(g)s and T(m)s of ionic liquids were determined by DSC.

  DOI：

  10.1021/jo026350g

文献信息

• Anti-hypercholesterolemic biaryl azetidinone compounds
  申请人：Morriello Gregori J.

  公开号：US20080280836A1

  公开（公告）日：2008-11-13

  This invention provides cholesterol absorption inhibitors of Formula I: and the pharmaceutically acceptable salts thereof, wherein R 12 is an alkyl, alkeny or alkynyl group mono- or poly-substituted with —OH, —COOH or a combination of —OH and —COOH, and R 9 contains an alkyl, alkeny or alkynyl group substituted with a heterocyclic ring, amino or sulfonyl. The compounds are useful for lowering plasma cholesterol levels, particularly LDL cholesterol, and for treating atherosclerosis and preventing atherosclerotic disease events.

  这项发明提供了化学式I的胆固醇吸收抑制剂及其药用盐，其中R12是一个烷基、烯烃或炔烃基，单取代或多取代于—OH、—COOH或—OH和—COOH的组合，而R9含有一个被杂环环、氨基或磺酰基取代的烷基、烯烃或炔烃基。这些化合物对降低血浆胆固醇水平，特别是LDL胆固醇，以及治疗动脉粥样硬化和预防动脉粥样硬化疾病事件具有用处。
• Synthesis and Sorption Analysis of Task-specific Fluorous Ionic Liquids
  作者：Verena Adamer、Gerhard Laus、Ulrich J. Griesser、Herwig Schottenberger

  DOI：10.5560/znb.2013-3142

  日期：2013.10.1

  Six 1-alkyl-4-tridecafluorooctyl-1,2,4-triazolium triflimides 2a-f and 4-amino-1-tridecafluorooctyl- 1,2,4-triazolium triflimide (4) were prepared from the respective iodides 1a-f (1a, 2a: n-propyl; 1b, 2b: n-butyl; 1c, 2c: n-hexyl; 1d, 2d: n-heptyl; 1e, 2e: n-octyl; 1f, 2f: n-decyl) and iodide 3 by ion metathesis. Compounds 2a and 4 are liquid at room temperature. Two liquid fluorous imidazolium salts bearing functionalized polar substituents were synthesized in an analogous manner, namely 1-(2- (diethylamino)ethyl)-3-(heptadecafluorodecyl)imidazolium triflimide (5b) and 1-(2-hydroxyethyl)- 3-(heptadecafluorodecyl)imidazolium triflimide (6b) from the respective bromides 5a and 6a. The bis(triflimide) 5c has a melting point slightly above room temperature. Three fluorous ionic liquids (ILs; 2a, 5b, and 6b) were subjected to vapor sorption analysis at 25 °C and exhibited dual affinity to water and, even much more pronounced, to methoxynonafluorobutane (hydrofluoroether HFE-7100). Thus, IL 6b absorbed 3:2% (by weight) water and 200% HFE, whereas ILs 2a and 5b absorbed 0.4 and 0:5% water, but 300 and 1200% HFE, respectively. Commercial 1-butyl-2,3- dimethyl-imidazolium triflimide and 1-ethyl-3-methyl-imidazolium triflimide were used as reference compounds and absorbed 0.9 and 2:2% water, respectively, but only 17% HFE.

  由各自的碘化物 1a-f 制备了六种 1-烷基-4-十三氟辛基-1,2,4-三唑三亚胺 2a-f 和 4-氨基-1-十三氟辛基-1,2,4-三唑三亚胺（4）（1a, 2a：1a，2a：正丙基；1b，2b：正丁基；1c，2c：正己基；1d，2d：正庚基；1e，2e：正辛基；1f，2f：正癸基）和碘化物 3 通过离子复分解反应制备而成。化合物 2a 和 4 在室温下呈液态。以类似的方法合成了两种带有官能化极性取代基的液态氟咪唑鎓盐，即 1-(2-(二乙基氨基)乙基)-3-(十七氟癸基)咪唑鎓三氟化物 (5b) 和 1-(2-羟乙基)-3-(十七氟癸基)咪唑鎓三氟化物 (6b)，它们分别来自各自的溴化物 5a 和 6a。双三亚胺 5c 的熔点略高于室温。对三种氟离子液体（ILs；2a、5b 和 6b）在 25 °C 下进行了蒸汽吸附分析，结果表明它们对水具有双重亲和力，对甲氧基壬基氟丁烷（氢氟醚 HFE-7100）的亲和力更为明显。因此，IL 6b 可吸收 3:2%（重量比）的水和 200% 的氢氟醚，而 IL 2a 和 5b 则分别可吸收 0.4% 和 0:5% 的水，但氢氟醚的吸收率分别为 300% 和 1200%。商用 1-丁基-2,3-二甲基-咪唑三氟利昂和 1-乙基-3-甲基-咪唑三氟利昂被用作参考化合物，它们分别吸收了 0.9% 和 2:2% 的水，但只吸收了 17% 的 HFE。
• New Quaternary Polyfluoroalkyl-1,2,4-Triazolium Salts Leading to Ionic Liquids
  作者：Jean’ne M. Shreeve、Yousef R. Mirzaei

  DOI：10.1055/s-2003-36254

  日期：——

  1-Alkyl-1,2,4-triazoles were quaternized at N-4 in >98% isolated yields using polyfluoroalkyl halides under neat reaction conditions at 100-120 °C to form 1-R-4-Rf-triazolium (Taz) halides. Metathesis of these polyfluoroalkylated triazolium halides with fluorine-containing anions led to the formation of new ionic liquids, [R(Rf)Taz]+Y-.

  在 100-120 °C 的纯净反应条件下，使用多氟烷基卤化物在 N-4 处对 1-烷基-1,2,4-三唑进行季铵化反应，生成 1-R-4-Rf 三唑（Taz）卤化物，分离收率大于 98%。这些多氟烷基化的三唑鎓卤化物与含氟阴离子发生 Metathesis 反应，生成了新的离子液体 [R(Rf)Taz]+Y-。
• Verfahren zur Herstellung von 1-(2-(2,4-Dichlorphenyl)pentyl)-1H-1,2,4-triazol und neue Hydrazon- oder Hydrazinderivate
  申请人：CIBA-GEIGY AG

  公开号：EP0097617A1

  公开（公告）日：1984-01-04

  1-[2-(2,4-Dichlorphenyl)pentyl]-1H-7,2,4-triazol kann nach einem neuen einfachen und wirtschaftlichen Verfahren in isomerenfreier Form hergestellt werden, indem man 2-(2,4-Dichlorphenyl)-valero-nitril in Gegenwart von Wasserstoff, einer Säure und eines Hydrierungskatalysators mit einer Verbindung H2N-NH-R zu einer Verbindung der Formel umsetzt, die Verbindung (III) katalytisch zu einer Verbindung hydriert, Verbindungen (IV) mit R ungleich H hydrolysiert und die Verbindungen (IV) mit R=H oder Salze davon mit Formamid und/oder [3-(Dimethylamino)-2-azaprop-2-en-1-yliden]-dimethylammoniumchlorid in das 1-[2-(2,4-Dichlorphenyl)pentyl]-1H-1,2,4-triazol überführt, oder Verbindungen (IV) mit R = -COR' mit wässriger Ameisensäure in die entsprechenden N,N'-Bisformylderivate überführt und diese mit Formamid, gegebenenfalls in Gegenwart von NH3, zum 1-[2-(2,4-Dichlorphenyl)pentyl)-1H-1,2,4-triazol umsetzt. Dabei ist R Wasserstoff, -CHO, -COR', -COOR' oder -CONH2 und R' bedeutet C1-4-Alkyl, Benzyl oder Phenyl. Das 1-[2-(2,4-Dichlorphenyl)-pentyl)-1H-1,2,4-triazol besitzt funizide Wirkung und kann zur Bekämpfung phytopathogener Pilze verwendet werden.

  1-[2-(2,4-二氯苯基)戊基]-1H-7,2,4-三唑可以通过一种简单而经济的新工艺制备，其方法是在氢、酸和氢化催化剂存在下，使 2-(2,4-二氯苯基)戊腈与化合物 H2N-NH-R 反应，得到式如下的化合物 将化合物 (III) 催化氢化成一种化合物 水解 R 不等于 H 的化合物 (IV)，并将 R=H 的化合物 (IV) 或其盐与甲酰胺和/或 [3-（二甲基氨基）-2-氮丙-2-烯-1-亚基]-二甲基氯化铵一起转化为 1-[2-（2,4-二氯苯基）戊基]-1H-1,2、4-三唑，或 R = -COR' 的化合物 (IV) 与甲酸水溶液反应生成相应的 N,N'-双甲酰基衍生物，再与甲酰胺反应（可选择在 NH3 存在的情况下），生成 1-[2-(2,4-二氯苯基)戊基]-1H-1,2,4-三唑。其中 R 是氢、-CHO、-COR'、-COOR'或-CONH2，R'是 C1-4 烷基、苄基或苯基。1-[2-(2,4- 二氯苯基)-戊基)-1H-1,2,4-三唑具有杀菌作用，可用于防治植物病原真菌。
• Azole derivatives of spiroheterocycles
  申请人：UNIROYAL CHEMICAL COMPANY, Inc.

  公开号：EP0341846A2

  公开（公告）日：1989-11-15

  A compound having the structural formula where R is C₂-C₈ alkylene having 2 to 4 carbon atoms linking X and Y; R¹ is C₁-C₈ linear or branched alkylene, C₁-C₆ oxyalkylene, C₁-C₆ thioalkylene or C₁-C₆ aminoalkylene; R² and R³ are the same or different and are hydrogen, halogen, C₁-C₈ alkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆ alkylsulfonyl, phenyl, substituted phenyl, phenoxy, substituted phenoxy, cyano, nitro, -OCOR⁴, -COOR⁵, -CHmQ3-m or -OCHmQ3-m; R⁴ is C₁-C₄ alkyl; R⁵ is hydrogen or C₁-C₄ alkyl; Q is halogen; X and Y are the same or different and are oxygen, sulfur, sulfinyl, sulfonyl or if one is NH, the other is sulfur; Z is nitrogen or CH; and m is 1, 2 or 3; and physiologically acceptable salts thereof, is disclosed. A process for synthesizing the compound of this invention is also set forth. This process involves reacting a compound having the structural formula where R¹, R², R³ and Z have the meanings given for the compound of this invention with a compound having the structural formula HX-R-YH where R, X and Y have the meanings given for the compound of the present invention. The compounds of this invention find utility as fungicides and plant growth regulants. Thus, the instant invention is also directed to processes for controlling fungi and regulating plant growth by utilizing effective amounts of the compound of the present invention to effectuate these goals. Finally, fungicidal and plant growth regulant compositions comprising effective amounts of the compound of this invention and carriers therefor is within the contemplation of the present invention.

  结构式如下的化合物 其中 R 是连接 X 和 Y 的具有 2 至 4 个碳原子的 C₂-C₈ 亚烷基； R¹ 是 C₁-C₈ 直链或支链亚烷基、C₁-C₆ 氧亚烷基、C₁-C₆ 硫亚烷基或 C₁-C₆ 氨基亚烷基； R² 和 R³ 相同或不同，并且是氢、卤素、C₁-C₈ 烷基、C₁-C₆ 烷氧基、C₁-C₆ 烷硫基、C₁-C₆烷基磺酰基、苯基、取代苯基、苯氧基、取代苯氧基、氰基、硝基、-OCOR⁴、-COOR⁵、-CHmQ3-m 或 -OCHmQ3-m； R⁴ 是 C₁-C₄ 烷基； R⁵ 是氢或 C₁-C₄ 烷基； Q 是卤素； X 和 Y 相同或不同，并且是氧、硫、亚砜基、磺酰基，或者如果一个是 NH，另一个是硫； Z 是氮或 CH；以及 m 为 1、2 或 3； 及其生理上可接受的盐类、 以及生理上可接受的盐。本发明还提出了一种合成本发明化合物的工艺。该工艺包括使结构式如下的化合物发生反应 其中 R¹、R²、R³ 和 Z 的含义与本发明化合物的含义相同。 HX-R-YH 其中 R、X 和 Y 的含义与本发明化合物相同。本发明的化合物可用作杀菌剂和植物生长调节剂。因此，本发明也适用于利用有效量的本发明化合物来达到控制真菌和调节植物生长的目的。最后，包含有效量的本发明化合物及其载体的杀真菌剂和植物生长调节剂组合物也在本发明的考虑范围之内。