(4R,5R)-1-benzyl-4,5-diphenyl-2-(2'-(diphenylphosphanyl)phenyl)-4,5-dihydro-1H-imidazole

• 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: (4R,5R)-1-benzyl-4,5-diphenyl-2-(2'-(diphenylphosphanyl)phenyl)-4,5-dihydro-1H-imidazole
• 英文别名: (4R,5R)-1-benzyl-2-(2-diphenylphosphanyl-phenyl)-4,5-diphenyl-4,5-dihydro-1H-imidazole；[2-[(4R,5R)-1-benzyl-4,5-diphenyl-4,5-dihydroimidazol-2-yl]phenyl]-diphenylphosphane
• 化学式: C₄₀H₃₃N₂P
• 分子量: 572.689
• InChiKey: BPMJUEJTGPGQAK-LJEWAXOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-fluoro-dithiobenzoic acid S-methyl ester 在 sodium hydride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (4R,5R)-1-benzyl-4,5-diphenyl-2-(2'-(diphenylphosphanyl)phenyl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  An efficient method for the synthesis of enantiopure phosphine–imidazoline ligands: application to the Ir-catalyzed hydrogenation of imines

  摘要：

  Phosphine-imidazoline ligands 8, and the derivatives 16 and 17, which have electron-withdrawing or electron-donating groups in the aminic nitrogen, were synthesized from 2-aryl-imidazo lines, which have previously been obtained from dithioesters. The coordination of ligand 8 to Ir(I) was studied and the molecular structure of the [Ir(eta(4) -COD)8]BF4 (COD = 1,5-cyclooctadiene) determined through X-ray diffraction. The in situ prepared Ir(I)/phosphine-imidazo line catalysts were tested in the asymmetric hydrogenation of ketimines in order to evaluate the influence of the electronic parameters of the ligand on the catalytic reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.013

文献信息

• Zwitterionic Iridium Complexes with P,N-Ligands as Catalysts for the Asymmetric Hydrogenation of Alkenes
  作者：Axel Franzke、Andreas Pfaltz

  DOI：10.1002/chem.201003314

  日期：2011.4.4

  Several zwitterionic iridium complexes based on chiral P,N‐ligands with imidazoline or oxazoline donors and anionic tetraarylborate or aryltrifluoroborate substituents have been synthesized. The corresponding cationic analogues have also been prepared, to evaluate the effect of the covalent linkage between the anion and the cationic metal complex in catalytic reactions. The respective pairs of structurally

  已经合成了几种基于手性P，N-配体与咪唑啉或恶唑啉供体以及阴离子四芳基硼酸酯或芳基三氟硼酸酯取代基的两性离子铱配合物。还制备了相应的阳离子类似物，以评估阴离子与阳离子金属络合物之间的共价键在催化反应中的作用。已经比较了各对结构类似的预催化剂在未官能化烯烃的不对称氢化中的功效。在大多数情况下，阴离子衍生化实际上对铱络合物的不对称诱导没有影响。这与X射线结构研究一致，该研究表明，阳离子金属中心的手性环境不受阴离子取代基的影响。
• Changing the Palladium Coordination to Phosphinoimidazolines with a Remote Triazole Substituent
  作者：Verónica de la Fuente、Rocío Marcos、Xacobe C. Cambeiro、Sergio Castillón、Carmen Claver、Miquel A. Pericàs

  DOI：10.1002/adsc.201100684

  日期：2011.12

  Phosphinoimidazoline (PHIM) ligands bearing a triazolylmethyl substituent at the sp3 nitrogen atom in the imidazoline ring lead to highly improved enantioselectivity (up to 99% ee) in allylic substitution reactions with respect to analogous ligands with substituents lacking the triazole unit. NMR and theoretical studies support a shift in the coordination mode of the PHIM ligand to palladium, triggered

  在咪唑啉环的sp 3氮原子上带有三唑基甲基取代基的膦亚咪唑啉（PHIM）配体，相对于具有缺少三唑单元的取代基的类似配体而言，在烯丙基取代反应中极大地提高了对映选择性（高达99％ee）。NMR和理论研究支持PHIM配体与钯的配位模式转变，这是由于与三唑单元发生非常有利的相互作用而引起的。