(2R,4S,5S)-5-amino-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohexane | 1351530-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,4S,5S)-5-amino-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohexane
• 英文别名: (2R,4S,5S)-2-naphthalen-1-yl-4-phenyl-1,3-dioxan-5-amine
• CAS: 1351530-48-7
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: XUWSMODRXWTOEQ-SLFFLAALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-萘甲醛 、 (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propandiol-hydrobromid 在 四磷十氧化物 作用下， 以5.3 g的产率得到(2R,4S,5S)-5-amino-2-(1-naphthyl)-4-phenyl-1,3-dioxacyclohexane
  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

文献信息

• Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions
  作者：Martin Steinbeck、Guido D. Frey、Wolfgang W. Schoeller、Wolfgang A. Herrmann

  DOI：10.1016/j.jorganchem.2011.04.001

  日期：2011.12

  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.