1-methylimidazol-4-yldiphenylphosphane | 1318212-66-6

• 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-methylimidazol-4-yldiphenylphosphane
• 英文别名: (1-methylimidazol-4-yl)diphenylphosphine；1-methylimidazole-4-yldiphenylphosphine；(1-Methylimidazol-4-yl)-diphenylphosphane；(1-methylimidazol-4-yl)-diphenylphosphane
• CAS: 1318212-66-6
• 化学式: C₁₆H₁₅N₂P
• 分子量: 266.282
• InChiKey: MHSIJYDAGRHPIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (tetrahydrothiophene)gold(I) chloride 、 乙醚 、 二氯甲烷 、 1-methylimidazol-4-yldiphenylphosphane 以 二氯甲烷 为溶剂， 以66%的产率得到[((1-methylimidazol-4-yl)diphenylphosphane)AuCl]*1/2CH2Cl2*1/4C4H10O
  参考文献：
  名称：

  Gold(I) Catalysts with Bifunctional P, N Ligands

  摘要：

  A series of phosphanes with imidazolyl substituents were prepared as hemilabile PN ligands. The corresponding gold(I) complexes were tested as bifunctional catalysts in the Markovnikov hydration of 1-octyne, as well as in the synthesis of propargylamines by the three component coupling reaction of piperidine, benzaldehyde, and phenylacetylene. While the activity in the hydration of 1-octyne was low, the complexes are potent catalysts for the three component coupling reaction. In homogeneous solution the conversions to the respective propargylamine were considerably higher than under aqueous biphasic conditions. The connectivity of the imidazolyl substituents to the phosphorus atom, their substitution pattern, as well as the number of heteroaromatic substituents have pronounced effects on the catalytic activity of the corresponding gold(I) complexes. Furthermore, formation of polymetallic species with Au-2, Au-3, and Au-4 units has been observed and the solid-state structures of the compounds [(5)(2)Au3Cl2]Cl and [(3c)(2)Au4Cl2]Cl-2 (3c = tris(2-isopropylimidazol-4(5)-yl phosphane, 5 = 2-tert-butylimidazol-4(5)-yldiphenyl phosphane) were determined. The gold(I) complexes of imidazol-2-yl phosphane ligands proved to be a novel source for bis(NHC)gold(I) complexes (NHC = N-heterocyclic carbene).

  DOI：

  10.1021/ic2011259
• 作为产物：
  描述：

  二苯基氯化膦 、 4-碘-1-甲基咪唑 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到1-methylimidazol-4-yldiphenylphosphane
  参考文献：
  名称：

  1JPSe耦合常数是膦碱度的可靠探针吗？A31P 核磁共振研究

  摘要：

  摘要 不同的杂芳基和官能化芳基取代基对杂芳基膦和二膦中磷原子的给电子能力和碱性的影响已通过使用相应硒化物的直接 1JPSe 偶联常数确定。讨论了使用 31P-77Se 自旋-自旋耦合常数作为膦碱度的探针的一般性以及该概念的范围和限制。图形概要

  DOI：

  10.1080/10426507.2010.547892

文献信息

• Is the¹<i>J</i>_PSeCoupling Constant a Reliable Probe for the Basicity of Phosphines? A³¹P NMR Study
  作者：Udo Beckmann、Diyana Süslüyan、Peter C. Kunz

  DOI：10.1080/10426507.2010.547892

  日期：2011.10

  functionalized aryl substituents on the electron-donating ability and basicity of the phosphorus atoms in heteroaryl phosphines and diphosphines has been determined by the use of the direct 1JPSe coupling constants of the corresponding selenides. The generality of the use of 31P–77Se spin–spin coupling constants as probe for the basicity of phosphines is discussed as well as the scope and limits of this concept

  摘要 不同的杂芳基和官能化芳基取代基对杂芳基膦和二膦中磷原子的给电子能力和碱性的影响已通过使用相应硒化物的直接 1JPSe 偶联常数确定。讨论了使用 31P-77Se 自旋-自旋耦合常数作为膦碱度的探针的一般性以及该概念的范围和限制。图形概要
• Gold(I) Catalysts with Bifunctional P, N Ligands
  作者：Corinna Wetzel、Peter C. Kunz、Indre Thiel、Bernhard Spingler

  DOI：10.1021/ic2011259

  日期：2011.8.15

  A series of phosphanes with imidazolyl substituents were prepared as hemilabile PN ligands. The corresponding gold(I) complexes were tested as bifunctional catalysts in the Markovnikov hydration of 1-octyne, as well as in the synthesis of propargylamines by the three component coupling reaction of piperidine, benzaldehyde, and phenylacetylene. While the activity in the hydration of 1-octyne was low, the complexes are potent catalysts for the three component coupling reaction. In homogeneous solution the conversions to the respective propargylamine were considerably higher than under aqueous biphasic conditions. The connectivity of the imidazolyl substituents to the phosphorus atom, their substitution pattern, as well as the number of heteroaromatic substituents have pronounced effects on the catalytic activity of the corresponding gold(I) complexes. Furthermore, formation of polymetallic species with Au-2, Au-3, and Au-4 units has been observed and the solid-state structures of the compounds [(5)(2)Au3Cl2]Cl and [(3c)(2)Au4Cl2]Cl-2 (3c = tris(2-isopropylimidazol-4(5)-yl phosphane, 5 = 2-tert-butylimidazol-4(5)-yldiphenyl phosphane) were determined. The gold(I) complexes of imidazol-2-yl phosphane ligands proved to be a novel source for bis(NHC)gold(I) complexes (NHC = N-heterocyclic carbene).
• Ruthenium piano-stool complexes bearing imidazole-based PN ligands
  作者：Peter C. Kunz、Indre Thiel、Anna Louisa Noffke、Guido J. Reiß、Fabian Mohr、Bernhard Spingler

  DOI：10.1016/j.jorganchem.2011.10.006

  日期：2012.1

  cyclopentadienyl ruthenium(II) with imidazole-based PN ligands have been synthesized starting from the precursor complexes [CpRu(C10H8)]PF6, [CpRu(NCMe)3]PF6 and [CpRu(PPh3)2Cl]. PN ligands used are imidazol-2-yl, -4-yl and -5-yl phosphines. Depending on the ligand and precursor different types of coordination modes were observed; in the case of polyimidazolyl PN ligands these were κ1P-monodentate, κ2P,N-, κ2N,N-

  从前体复合物[CpRu（C 10 H 8）] PF 6，[CpRu（NCMe）3 ] PF 6和[ CpRu（PPh 3）2 Cl]。所用的PN配体是咪唑-2-基，-4-基和-5-基膦。 取决于配体和前体，观察到不同类型的配位模式。在polyimidazolyl PN的情况下配体这些都是κ 1个P -monodentate，κ 2 P，N - ，κ 2 N，N- -和κ 3 N，N，N- -螯合剂和μ-κ P：κ 2 N，N-桥接。的固态结构[CPRU（1A）2 CL]·H 2 O（5 。 ħ 2 O）和[CPRU（μ-κ 2 -N，N- κ ' 1 -P -图2b）} 2 ] （C 6H 5 PO 3 H）2（C 6 H 5 PO 3 H 2）2也是确定的[CpRu（2b）} 2 ]（PF 6）2的水解产物。2CH 3 CN（7b中。 2CH 3 CN）进行了测定（1A  =咪唑-2-