tetrabutylammonium imidazolide | 67035-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tetrabutylammonium imidazolide
• 英文别名: tetrabutylammonium 1H-imidazolide；tetra-n-butylammonium imidazolate；[TBA]Im；Imidazol-3-ide;tetrabutylazanium；imidazol-3-ide;tetrabutylazanium
• CAS: 67035-78-3
• 化学式: C₃H₃N₂*C₁₆H₃₆N
• 分子量: 309.539
• InChiKey: QKYLNTUDAQZTHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  13.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrabutylammonium imidazolide 、 Alpha-(氯甲基)-2,4-二氯苯甲醇 以 乙腈 为溶剂， 以68%的产率得到alpha-(2,4-二氯苯基)-1H-咪唑-1-乙醇
  参考文献：
  名称：

  New copper(II) complexes with isoconazole: Synthesis, structures and biological properties

  摘要：

  There is an increasing demand for novel metal-based complexes with biologically relevant molecules in technology and medicine. Three new Cu(II) coordination compounds with antifungal agent isoconazole (L), namely mononuclear complexes [CuCl2(L)(2)] (1), and [Cu(O2CMe)(2)(L)(2)]center dot 2H(2)O (2) and coordination polymer [Cu(pht)(L)(2)](n) (3) (where H(2)pht - o-phthalic acid) were synthesized and characterized by IR spectroscopy, thermogravimetric analysis and X-ray crystallography. X-ray analysis showed that in all complexes, the isoconazole is coordinated to Cu(II) centres by a N atom of the imidazole fragment. In complex I, the square-planar environment of Cu(II) atoms is completed by two N atoms of isoconazole and two chloride ligands, whereas the Cu(II) atoms are coordinated by two N atoms from two isoconazole ligands and two O atoms from the different carboxylate residues: acetate in 2 and phthalate in 3. The formation of an infinite chain through the bridging phthalate ligand is observed in 3. The biosynthetic ability of micromycetes Aspergillus niger CNMN FD 10 in the presence of the prepared complexes 1-3 as well as the antifungal drug isoconazole were studied. Complexes 2 and 3 accelerate the biosynthesis of enzymes (beta-glucosidase, xylanase and endoglucanase) by this fungus. Moreover, a simplified and improved method for the preparation of isoconazole nitrate was developed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.10.040
• 作为产物：
  描述：

  咪唑 、 四丁基溴化铵 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 以98%的产率得到tetrabutylammonium imidazolide
  参考文献：
  名称：

  New copper(II) complexes with isoconazole: Synthesis, structures and biological properties

  摘要：

  There is an increasing demand for novel metal-based complexes with biologically relevant molecules in technology and medicine. Three new Cu(II) coordination compounds with antifungal agent isoconazole (L), namely mononuclear complexes [CuCl2(L)(2)] (1), and [Cu(O2CMe)(2)(L)(2)]center dot 2H(2)O (2) and coordination polymer [Cu(pht)(L)(2)](n) (3) (where H(2)pht - o-phthalic acid) were synthesized and characterized by IR spectroscopy, thermogravimetric analysis and X-ray crystallography. X-ray analysis showed that in all complexes, the isoconazole is coordinated to Cu(II) centres by a N atom of the imidazole fragment. In complex I, the square-planar environment of Cu(II) atoms is completed by two N atoms of isoconazole and two chloride ligands, whereas the Cu(II) atoms are coordinated by two N atoms from two isoconazole ligands and two O atoms from the different carboxylate residues: acetate in 2 and phthalate in 3. The formation of an infinite chain through the bridging phthalate ligand is observed in 3. The biosynthetic ability of micromycetes Aspergillus niger CNMN FD 10 in the presence of the prepared complexes 1-3 as well as the antifungal drug isoconazole were studied. Complexes 2 and 3 accelerate the biosynthesis of enzymes (beta-glucosidase, xylanase and endoglucanase) by this fungus. Moreover, a simplified and improved method for the preparation of isoconazole nitrate was developed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.10.040
• 作为试剂：
  描述：

  二氧化碳 、 2-甲基-3-丁炔-2-醇 在 tetrabutylammonium imidazolide 作用下， 以 neat (no solvent) 为溶剂， 80.0 ℃ 、5.0 MPa 条件下， 反应 6.0h， 生成 4,4-二甲基-5-亚甲基-1,3-二氧戊环-2-酮 、 (1,1-dimethyl-2-oxopropyl)(1',1'-dimethyl-2'-propynyl)carbonate
  参考文献：
  名称：

  提高有机盐催化二氧化碳和丙醇快速选择性合成α-亚烷基环状碳酸酯的性能

  摘要：

  通过CO 2与炔丙醇的羧化偶联合成α-亚烷基环状碳酸酯（αCCs）受到越来越多的关注，但需要使用最常大量添加和/或缺乏选择性的催化剂。在此，我们将对铵型有机催化剂的结构进行微调，从而使我们能够确定决定其催化性能的重要结构参数。草酸四丁铵被证明是最有吸引力的有机催化剂之一，在无溶剂条件下以低催化剂负载量（2.5 mol％），能快速，完全和选择性地生产αCC。这项研究为从CO 2方便而选择性地合成αCCs文库开辟了新途径。 通过使用简单的有机催化剂和炔丙醇。

  DOI：

  10.1002/cctc.201800063

文献信息

• Protic ionic liquid-promoted synthesis of dimethyl carbonate from ethylene carbonate and methanol
  作者：Yu Song、Xing He、Bing Yu、Hong-Ru Li、Liang-Nian He

  DOI：10.1016/j.cclet.2019.07.053

  日期：2020.3

  the protic ionic liquid [DBUH][Im] (1,8-diazabicyclo[5.4.0]-7-undeceniumimidazolide) was developed as an efficient catalyst for the transesterification of ethylene carbonate with methanol to produce dimethyl carbonate. At 70 °C, up to 97% conversion of ethylene carbonate and 91% yield of dimethyl carbonate were obtained with 1 mol% [DBUH][Im] (relative to ethylene carbonate) as catalyst in 2 h. Even at

  摘要在这项工作中，质子离子液体[DBUH] [Im]（1,8-二氮杂双环[5.4.0] -7-十一碳铝咪唑化物）被开发为一种有效的催化剂，用于碳酸亚乙酯与甲醇的酯交换反应以生产碳酸二甲酯。在70°C下，用1 mol％[DBUH] [Im]（相对于碳酸亚乙酯）作为催化剂，在2小时内可获得高达97％的碳酸亚乙酯转化率和91％的碳酸二甲酯产率。即使在室温下，碳酸亚乙酯的转化率也可以达到94％，碳酸二甲酯的产率在6小时内可以达到81％。催化机理研究表明，这种离子液体的高催化效率是由协同活化作用引起的，其中阳离子可以活化碳酸亚乙酯，而阴离子可以通过氢键形成来活化甲醇。
• Imidazolate complexes of iron and manganese tetraphenylporphyrins
  作者：John T. Landrum、K. Hatano、W. Robert Scheidt、Christopher A. Reed

  DOI：10.1021/ja00542a011

  日期：1980.10
• Imidazolate- and oxo-bridged metalloporphyrins
  作者：John T. Landrum、David Grimmett、Kenneth J. Haller、W. Robert Scheidt、Christopher A. Reed

  DOI：10.1021/ja00400a027

  日期：1981.5
• Proton NMR study of the deprotonation of axial imidazole ligands in low-spin ferric porphyrin complexes
  作者：V. P. Chacko、Gerd N. La Mar

  DOI：10.1021/ja00389a019

  日期：1982.12
• New copper(II) complexes with isoconazole: Synthesis, structures and biological properties
  作者：Galina M. Dulcevscaia、Victor Ch. Kravtsov、Fliur Z. Macaev、Gheorghe G. Duca、Eugenia P. Stingachi、Serghei I. Pogrebnoi、Veaceslav V. Boldescu、Steliana F. Clapco、Janeta P. Tiurina、Alexandra A. Deseatnic-Ciloci、Janusz Lipkowski、Shi-Xia Liu、Silvio Decurtins、Svetlana G. Baca

  DOI：10.1016/j.poly.2012.10.040

  日期：2013.3

  There is an increasing demand for novel metal-based complexes with biologically relevant molecules in technology and medicine. Three new Cu(II) coordination compounds with antifungal agent isoconazole (L), namely mononuclear complexes [CuCl2(L)(2)] (1), and [Cu(O2CMe)(2)(L)(2)]center dot 2H(2)O (2) and coordination polymer [Cu(pht)(L)(2)](n) (3) (where H(2)pht - o-phthalic acid) were synthesized and characterized by IR spectroscopy, thermogravimetric analysis and X-ray crystallography. X-ray analysis showed that in all complexes, the isoconazole is coordinated to Cu(II) centres by a N atom of the imidazole fragment. In complex I, the square-planar environment of Cu(II) atoms is completed by two N atoms of isoconazole and two chloride ligands, whereas the Cu(II) atoms are coordinated by two N atoms from two isoconazole ligands and two O atoms from the different carboxylate residues: acetate in 2 and phthalate in 3. The formation of an infinite chain through the bridging phthalate ligand is observed in 3. The biosynthetic ability of micromycetes Aspergillus niger CNMN FD 10 in the presence of the prepared complexes 1-3 as well as the antifungal drug isoconazole were studied. Complexes 2 and 3 accelerate the biosynthesis of enzymes (beta-glucosidase, xylanase and endoglucanase) by this fungus. Moreover, a simplified and improved method for the preparation of isoconazole nitrate was developed. (C) 2012 Elsevier Ltd. All rights reserved.