1,3-di-[(2R,4S,5S)-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohex-5-yl]imidazolium perchlorate | 1351530-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,3-di-[(2R,4S,5S)-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohex-5-yl]imidazolium perchlorate
• CAS: 1351530-53-4
• 化学式: C₄₃H₃₇N₂O₄*ClO₄
• 分子量: 745.228
• InChiKey: WQNGPSJHDGXIJT-KSZFIFQQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  54.0
• 可旋转键数：
  6.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  137.97
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  二氯甲烷 、 1,3-di-[(2R,4S,5S)-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohex-5-yl]imidazolium perchlorate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 在 lithium tert-butanolate 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到chloro(η4-1,5-cyclooctadiene)(1,3-di-[(2R,4S,5S)-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohex-5-yl]imidazolin-2-ylidene)rhodium(I)*0.15CH2Cl2
  参考文献：
  名称：

  Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions

  摘要：

  Different chiral mono-substituted N-heterocyclic carbene complexes of rhodium were prepared, starting from [Rh(COD)Cl](2) (COD = cyclooctadiene) by addition of free N-heterocyclic carbenes (NHC), or an in-situ deprotonation of the corresponding iminium salt. All new complexes were characterized by spectroscopy methods. In addition, the structures of chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(1R,2R,3R,5S)-2,6,6- trimethylbicyclo[3.1.1]hept-3-yl] imidazolin-2-ylidene) rhodium(I) (5a), chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(1R,2S,5R)-2-isopropyl-5-menthylcyclohex-1-yl] imidazol-2-ylidene)rhodium(I) (5b) and chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(2R,4S,5S)-2-methyl-4-phenyl-1,3-dioxacyclohex-5-yl]imidazolin-2- ylidene)rhodium(I) (5i) were analyzed by DFT-calculations. The enantioselective hydrosilylation of acetophenone, ethylpyruvate and n-propylpyruvate with diphenylsilane and hydrolysis was carried out with chiral C-2-symmetrical mono-substituted N-heterocyclic carbene rhodium complexes giving for the first time an enantioselective excess of up to 74% ee in the case of the n-propylpyruvate. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.04.001
• 作为产物：
  描述：

  草酸醛 、 (2R,4S,5S)-5-amino-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohexane 在 聚合甲醛 、 高氯酸 作用下， 以 水 、 甲苯 为溶剂， 以39%的产率得到1,3-di-[(2R,4S,5S)-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohex-5-yl]imidazolium perchlorate
  参考文献：
  名称：

  Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions

  摘要：

  Different chiral mono-substituted N-heterocyclic carbene complexes of rhodium were prepared, starting from [Rh(COD)Cl](2) (COD = cyclooctadiene) by addition of free N-heterocyclic carbenes (NHC), or an in-situ deprotonation of the corresponding iminium salt. All new complexes were characterized by spectroscopy methods. In addition, the structures of chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(1R,2R,3R,5S)-2,6,6- trimethylbicyclo[3.1.1]hept-3-yl] imidazolin-2-ylidene) rhodium(I) (5a), chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(1R,2S,5R)-2-isopropyl-5-menthylcyclohex-1-yl] imidazol-2-ylidene)rhodium(I) (5b) and chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(2R,4S,5S)-2-methyl-4-phenyl-1,3-dioxacyclohex-5-yl]imidazolin-2- ylidene)rhodium(I) (5i) were analyzed by DFT-calculations. The enantioselective hydrosilylation of acetophenone, ethylpyruvate and n-propylpyruvate with diphenylsilane and hydrolysis was carried out with chiral C-2-symmetrical mono-substituted N-heterocyclic carbene rhodium complexes giving for the first time an enantioselective excess of up to 74% ee in the case of the n-propylpyruvate. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.04.001