(S)-(1-(2,6-diisopropylphenyl)-3-(1-hydroxy-3-phenylpropan-2-yl)imidazolidin-2-ylidene)gold(I) chloride | 1358742-85-4

• 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: (S)-(1-(2,6-diisopropylphenyl)-3-(1-hydroxy-3-phenylpropan-2-yl)imidazolidin-2-ylidene)gold(I) chloride
• CAS: 1358742-85-4
• 化学式: C₂₄H₃₂AuClN₂O
• 分子量: 596.95
• InChiKey: GFFUFDRRSIIIAL-FGJQBABTSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.71
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-2-(2-(2,6-diisopropylphenylamino)ethylamino)-3-phenylpropan-1-ol 在 potassium carbonate 、 氯化铵 作用下， 以 丙酮 为溶剂， 生成 (S)-(1-(2,6-diisopropylphenyl)-3-(1-hydroxy-3-phenylpropan-2-yl)imidazolidin-2-ylidene)gold(I) chloride
  参考文献：
  名称：

  金(I)-卡宾配合物催化的对映选择性环丙烷化

  摘要：

  在金 (I) 催化的烯烃和炔丙基酯的反应中形成多取代的环丙烷衍生物是产生多样性的潜在有用的转化，因此任何可以控制其立体选择性的方法都具有重要意义。我们制备并测试了一系列手性金 (I)-卡宾配合物作为该转化的催化剂。通过对反应条件的系统优化，我们能够在测试反应中实现高对映选择性，而顺式：反式转化的选择性与催化剂无关。使用优化的条件，我们对一系列不同的烯烃和乙炔衍生物进行了反应，发现虽然反应进行得很顺利，并且产物通常以良好的收率和良好的顺式选择性分离，但观察到的对映选择性变化很大，有时是适中的最好。我们无法建立任何结构-性质关系，这表明对于任何给定的试剂组合，必须单独确定最佳催化剂。

  DOI：

  10.3390/molecules27185805
• 作为试剂：
  描述：

  乙酸异丙烯酯 、 1,1-二甲基丙-2-炔基乙酸酯 在 (S)-(1-(2,6-diisopropylphenyl)-3-(1-hydroxy-3-phenylpropan-2-yl)imidazolidin-2-ylidene)gold(I) chloride 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [1-[(1R,2R)-2-acetyloxy-2-methylcyclopropyl]-2-methylprop-1-enyl] acetate 、 1-(2-acetoxy-2-methylcyclopropyl)-2-methylprop-1-en-1-yl acetate 、 [1-[(1S,2R)-2-acetyloxy-2-methylcyclopropyl]-2-methylprop-1-enyl] acetate 、 [1-[(1S,2S)-2-acetyloxy-2-methylcyclopropyl]-2-methylprop-1-enyl] acetate
  参考文献：
  名称：

  Synthesis of amino acid derived imidazolidinium salts as new NHC precatalysts

  摘要：

  The preparation of new chiral symmetrically and unsymmetrically N,N'-disubstituted imidazolium based NHC salts Ib, IIb, IIIa-c and IVc-h from the amino acids L-proline and L-phenylalanine, is reported. Some preliminary tests have been carried out, demonstrating that the chiral NHCs give chiral induction in organometallic catalysis and can be used as organocatalysts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.015

文献信息

• Chiral NHC Ligands for Enantioselective Gold(I) Catalysis Under Aerobic Conditions: the Importance of Conformational Flexibility and Steric Hindrance of NHC Ligand on Reactivity
  作者：Michał Michalak、Paweł Czerwiński、Katarzyna Śniady‐Maciążek、Szymon Musioł、Oksana Danylyuk、Michał Wierzbicki、Michele Tomasini、Albert Poater

  DOI：10.1002/chem.202303241

  日期：2024.3

  of chiral NHC−Au−Cl complexes, bearing sterically encumbered NHC ligands, has been accessed by merging anilines with commercially available chiral aminoalcohols and amines. Evaluation of the catalytic activity in enantioselective allenol cyclization has pointed out the importance of the steric hindrance and conformational flexibility of the NHC core for reactivity. Ion metathesis between NHC−Au−Cl

  位阻但活跃：通过将苯胺与市售手性氨基醇和胺合并，获得了一个新的手性 NHC−Au−Cl 配合物家族，带有位阻 NHC 配体。对映选择性二烯醇环化催化活性的评估指出了 NHC 核心的空间位阻和构象灵活性对于反应活性的重要性。与 DCM 相比，金络合物活化所需的 NHC−Au−Cl 和 AgOT 之间的离子复分解在常用的 MeNO 2中似乎非常缓慢。
• Asymmetric induction afforded by chiral azolylidene N-heterocyclic carbenes (NHC) catalysts
  作者：Ragnhild B. Strand、Trygve Helgerud、Tina Solvang、Amund Dolva、Christian A. Sperger、Anne Fiksdahl

  DOI：10.1016/j.tetasy.2012.09.004

  日期：2012.10

  Screening studies of new chiral imidazolium and triazolium based NHC salts I-VIII as ligands in asymmetric organometallic catalysis and as organocatalysts showed that these catalysts efficiently promoted the reactions. Moderate enantioselectivities (55-57% ee) were obtained in the asymmetric Cu-NHC catalysed conjugate additions of diethylzinc to cyclohexenone, in accordance with most previous studies. The chiral induction afforded in the gold(I)-NHC catalysed cyclopropanation reactions was low (< 28% ee). However, these results represent the first reported chiral gold(I)-NHC catalysed olefin cyclopropanation. The NHC-organocatalysed asymmetric cross-annulation of cinnamaldehyde and trifluoroacetophenone gave lower enantioselectivity (< 50% ee) but higher yields of the gamma-lactone product relative to previous reports. The enantioselectivities obtained varied considerably, even within a group of structurally closely related NHCs. This study demonstrates the challenge of designing NHCs with a general ability to induce asymmetry in a broader range of reactions. (C) 2012 Elsevier Ltd. All rights reserved.