(R)-benzoyl-(1,1'-binaphthyl-2,2'-diyl)phosphite

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-benzoyl-(1,1'-binaphthyl-2,2'-diyl)phosphite
• 英文别名: 12,14-Dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl benzoate
• 化学式: C₂₇H₁₇O₄P
• 分子量: 436.403
• InChiKey: NCWPPWJCVJKOGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium benzoate 、 (R)-(1,1′-联萘-2,2′-二氧)氯膦 以 四氢呋喃 为溶剂， 反应 4.0h， 以87%的产率得到(R)-benzoyl-(1,1'-binaphthyl-2,2'-diyl)phosphite
  参考文献：
  名称：

  BINOL derived monodentate acylphosphite ligands for homogeneously catalyzed enantioselective hydrogenation

  摘要：

  Enantiopure acylphosphites have been prepared based upon chiral nonsubstituted and 3,3'-disubstituted binaphthols in order to elucidate steric and electronic effects on the Rh(I)-catalyzed asymmetric hydrogenation of functionalized olefins. With these new types of ligands, up to 80% ee was obtained. Rate as well as enantio selectivity of the hydrogenation were strongly dependent on the precatalyst preparation and substitution pattern of the ligand. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.012
• 作为试剂：
  描述：

  衣康酸二甲酯 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 、 (R)-benzoyl-(1,1'-binaphthyl-2,2'-diyl)phosphite 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 1.67h， 生成 R-2-甲基琥珀酸甲酯 、 (S)-dimethyl 2-methylsuccinate
  参考文献：
  名称：

  BINOL derived monodentate acylphosphite ligands for homogeneously catalyzed enantioselective hydrogenation

  摘要：

  Enantiopure acylphosphites have been prepared based upon chiral nonsubstituted and 3,3'-disubstituted binaphthols in order to elucidate steric and electronic effects on the Rh(I)-catalyzed asymmetric hydrogenation of functionalized olefins. With these new types of ligands, up to 80% ee was obtained. Rate as well as enantio selectivity of the hydrogenation were strongly dependent on the precatalyst preparation and substitution pattern of the ligand. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.012

文献信息

• BINOL derived monodentate acylphosphite ligands for homogeneously catalyzed enantioselective hydrogenation
  作者：Andrei Korostylev、Axel Monsees、Christine Fischer、Armin Börner

  DOI：10.1016/j.tetasy.2004.01.012

  日期：2004.3

  Enantiopure acylphosphites have been prepared based upon chiral nonsubstituted and 3,3'-disubstituted binaphthols in order to elucidate steric and electronic effects on the Rh(I)-catalyzed asymmetric hydrogenation of functionalized olefins. With these new types of ligands, up to 80% ee was obtained. Rate as well as enantio selectivity of the hydrogenation were strongly dependent on the precatalyst preparation and substitution pattern of the ligand. (C) 2004 Elsevier Ltd. All rights reserved.