(2-imidazol-1-ylphenyl)diphenylphosphine | 953429-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-imidazol-1-ylphenyl)diphenylphosphine
• 英文别名: 1-(2-diphenylphosphino)-1H-imidazole
• CAS: 953429-65-7
• 化学式: C₂₁H₁₇N₂P
• 分子量: 328.353
• InChiKey: LLJBRIABSOMTPF-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C(Solv: tetrahydrofuran (109-99-9); pentane (109-66-0))
• 沸点：
  482.6±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2-imidazol-1-ylphenyl)diphenylphosphine 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 12.0h， 以95%的产率得到
  参考文献：
  名称：

  二氨基卡宾-叶立德phosph：直接获得C，C螯合配体。

  摘要：

  DOI：

  10.1002/anie.200701490
• 作为产物：
  描述：

  1-苯基咪唑 、 二苯基氯化膦 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以65%的产率得到(2-imidazol-1-ylphenyl)diphenylphosphine
  参考文献：
  名称：

  二氨基卡宾-叶立德phosph：直接获得C，C螯合配体。

  摘要：

  DOI：

  10.1002/anie.200701490

文献信息

• On the P-Coordinating Limit of NHC-Phosphenium Cations toward Rh^ICenters
  作者：Carine Maaliki、Christine Lepetit、Yves Canac、Christian Bijani、Carine Duhayon、Remi Chauvin

  DOI：10.1002/chem.201104046

  日期：2012.6.18

  P‐coordinating ability toward a RhCl(cod)} (cod=cycloocta‐1,5‐diene) center, thus competing with the cleavage of the labile CP bond. Derivatives of N,N′‐phenylene‐bridged diimidazolylphenylphosphane were isolated in good yield. Whereas the dicationic phosphane proved to be inert in the presence of [RhCl(cod)}2], the monocationic counterpart was shown to retain the P‐coordinating ability toward a RhCl(cod)}

  通过实验描述并从理论上研究了两种类型的带有额外吸电子取代基的咪唑并二膦基化合物，例如烷氧基或咪唑并基团。二Ñ，Ñ '-2,4,6-甲基（苯基）imidazoliophosphonite被示出为保留向P-协调能力的的RhCl（COD）}（COD =环辛-1,5-二烯）中心，从而与竞争不稳定的CP键的裂解。以高收率分离出N，N'-亚苯基桥连的二咪唑基苯基膦的衍生物。事实证明，在[RhCl（cod）} 2的存在下，磷化膦是惰性的]，单阳离子对应物显示出对RhCl（cod）}中心的P配位能力，因此与未甲基化的咪唑基取代基的N配位能力竞争。还表征了该指示剂的乙基次膦酸酯版本，因此具有极低的P III中心。根据计算出的均相和异相解离能之间的差异，N 2咪唑并膦在P原子上具有芳基，氨基或烷氧基取代基的C⋅⋅⋅P键被证明具有定性性质。通过比较相应的HOMO和LUMO，分析了P原子上具有苯基或乙氧基
• Diaminocarbene and Phosphonium Ylide Ligands: A Systematic Comparison of their Donor Character
  作者：Yves Canac、Christine Lepetit、Mohammed Abdalilah、Carine Duhayon、Remi Chauvin

  DOI：10.1021/ja801159v

  日期：2008.7.1

  The coordinating properties of the diaminocarbene (A) and phosphonium ylide (B) ligand types have been investigated systematically through a test family of C,C-chelating ligands containing two moieties of either kind. The overall character of o-C(6)H(4)A(a)B(b) ligands (a + b = 2) has been analyzed from the IR CO stretching frequencies of isostructural complexes [(eta(2)-C(6)H(4)A(a)B(b))Rh(CO)(2)][TfO]. The test moieties A = NC2H2N+(Me)C- and B = Ph2P+CH2- were first considered. While the ligands bearing at least one diaminocarbene end (AA, a = 2 and AB, a = 1) could be generated (and trapped by complexation), the bis-ylide case BB (a = 0) proved to be awkward: treatment of the dication C6H4(P+Ph2Me)(2) with n-BuLi indeed lead to the Schmidbaur's carbodiphosphorane Ph3P=C=PPh2Me, through an unprecendented ylido-pentacoordinated phosphorane which could be fully characterized by NMR techniques. The bis-ylide ligand type C6H4B2 could however be generated by bridging the phosphonium methyl groups by a methylene link (B-2 = (P+Ph2CH-)(2)CH2), preventing the formation of the analogous highly strained carbodiphosphorane. The three complexes [(eta(2)-C(6)H(4)A(a)B(b))Rh(CO)(2)][TfO] were fully characterized, including by X-ray diffraction analysis and Rh-103 NMR spectroscopy. Comparison of their IR spectra indicated that the A(2) type bis-NHC ligand is less donating than the hybrid AB type, which is itself less donating than the B-2 type bis-ylide ligand. The excellent linear variation of the nu(CO) frequencies vs a (= 0, 1, 2) shows that the coordinating moieties act in a pseudoindependent way. This was confirmed by DFT calculations at the B3PW91/6-31G(star star)/LANL2DZ(star)(Rh) level. It is therefore demonstrated that a phosphonium ylide ligand is a stronger donor than a diaminocarbene ligand.