1H-咪唑-2-基(二苯基)膦 | 289884-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1H-咪唑-2-基(二苯基)膦
• 英文名称: (imidazol-2-yl)diphenylphosphane
• 英文别名: 2-(diphenylphosphino)imidazole；imidazol-2-yldiphenylphosphine；1H-Imidazole, 2-(diphenylphosphino)-；1H-imidazol-2-yl(diphenyl)phosphane
• CAS: 289884-71-5
• 化学式: C₁₅H₁₃N₂P
• 分子量: 252.255
• InChiKey: QHLCEDRGWVXPMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.5±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1H-咪唑-2-基(二苯基)膦 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 50.0h， 生成 2-diphenylphosphoryl-1H-imidazole
  参考文献：
  名称：

  “无痕”施陶丁格连接，用于酰胺键的化学选择性合成。

  摘要：

  [反应：见正文]在这里，我们报告了对我们先前报道的“斯托丁格连接”的一种新颖修饰，该修饰从叠氮化物和经过特殊功能化的膦生成酰胺键。不需要远端官能团的正交保护的这种选择性形成酰胺键的方法应该在合成和生物化学中找到通用的用途。

  DOI：

  10.1021/ol006054v
• 作为产物：
  描述：

  2-(diphenylphosphino)-1-(diethoxymethyl)imidazole 在 甲醇 、 三甲基氯硅烷 作用下， 以 正戊烷 为溶剂， 以8.66 g的产率得到1H-咪唑-2-基(二苯基)膦
  参考文献：
  名称：

  带有NH基团的咪唑基膦的Cp*Ir配合物中二次相互作用的多模态研究

  摘要：

  使用 X 射线衍射、核磁共振和红外光谱以及 DFT 计算的组合来探索氢键现象。三种咪唑基膦 R(2)PImH（ImH = 咪唑-2-基，R = 叔丁基、异丙基、苯基、1a-1c）和缺乏咪唑的对照膦 (i-Pr)(2)PhP (1d)用于制备一系列 Cp*Ir(L(1))(L(2))(膦) 形式的配合物。此外，为了抑制与任一咪唑氮 1e 的分子间相互作用，制备了 1b 的二（异丙基）咪唑基类似物及其双 (15)N 标记的同位素异构体，以探索每个咪唑氮上的键合相互作用。当使用咪唑基膦配体 1b 时，可以看到转移氢化速率的适度提高。二氯配合物 (L(1) = L(2) = Cl, 2a-2c, 2e) 显示了分子内氢键，如四个 X 射线结构和各种 NMR 和 IR 数据所揭示的。值得注意的是，氢化物氯化物复合物 [L(1) = H, L(2) = Cl, 3a-3c 和 3e-((15)N)(2)]

  DOI：

  10.1021/ja906712g

文献信息

• 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-
• Compositions and methods for hydration of terminal alkynes
  申请人：San Diego State University Foundation

  公开号：US20020115860A1

  公开（公告）日：2002-08-22

  Compositions and methods are described for hydrating terminal alkynes catalytically in anti-Markovnikov fashion. The compositions comprise a transition metal complex including at least one organic ligand having at least two heteroatoms, wherein the heteroatoms are directly bonded or located one atom away. Preferably, at least one of the heteroatoms is nitrogen, which is typically provided as part of a heterocyclic ring. Other preferred heteroatoms include S, P, N, As or Se. A particularly preferred catalyst employs a P-linked imidazole ligand bound to Ru. Such complexes have a controlled adaptable proton transfer ability and/or a hydrogen bonding ability making them particularly useful as chemical reaction facilitators.

  描述了一种以反马可夫尼科夫方式催化水合末端炔烃的组合物和方法。这些组合物包括至少一个有至少两个杂原子的有机配体的过渡金属配合物，其中这些杂原子直接键合或位于一个原子之外。最好的情况是，这些杂原子中至少有一个是氮，通常作为杂环的一部分提供。其他首选的杂原子包括硫、磷、氮、砷或硒。一种特别首选的催化剂使用与钌结合的P-链咪唑配体。这种复合物具有可控的适应性质子转移能力和/或氢键能力，使它们特别适用于化学反应促进剂。
• CHEMOSELECTIVE LIGATION
  申请人：Saxon Eliana

  公开号：US20080214801A1

  公开（公告）日：2008-09-04

  The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

  本发明涉及一种可在生理条件下进行的化学选择性连接反应。一般而言，该发明涉及特别设计的膦化合物的缩合反应，该膦化合物可以提供在两个反应物之间形成酰胺键的反应，从而产生包含膦基团的最终产物，或者可以被设计成包含可切断的连接剂，以便将膦的取代基转移到偶氮化物上，释放氧化的膦副产物并在最终产物中产生天然的酰胺键。该反应的选择性及其与水环境的兼容性使其适用于体内应用（例如，在细胞表面或细胞内）和体外应用（例如，合成肽和其他聚合物，生产修饰（例如，标记）的氨基酸）。
• CHEMOSELECTIVE LIGATION
  申请人：SAXON Eliana

  公开号：US20070037964A1

  公开（公告）日：2007-02-15

  The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

  本发明涉及一种可以在生理条件下进行的化学选择性连接反应。一般来说，该发明涉及特定设计的膦化合物的缩合作用，该膦化合物可以提供两个反应物之间的酰胺键形成，从而产生一个包含膦基团的最终产物，或者可以被设计成包含可裂解的连接剂，使膦的取代基转移到叠氮化合物上，释放出一个氧化膦副产物，并在最终产物中产生一个天然的酰胺键。该反应的选择性及其与水性环境的兼容性使其可以应用于体内（例如在细胞表面或细胞内）和体外（例如合成肽和其他聚合物，生产改性（例如标记）氨基酸）。
• 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).