(2R,3R)-2,3-O-Bis(diphenylphosphinoxy)weinsaeurediethylester | 102139-89-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R)-2,3-O-Bis(diphenylphosphinoxy)weinsaeurediethylester
• 英文别名: diethyl (2R,3R)-2,3-bis[(diphenylphosphino)oxy]succinate；diethyl (2R,3R)-2,3-bis(diphenylphosphanyloxy)butanedioate
• CAS: 102139-89-9
• 化学式: C₃₂H₃₂O₆P₂
• 分子量: 574.55
• InChiKey: AVYFMWSAUCWMCA-LOYHVIPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  L-(+)-酒石酸二乙酯 以94%的产率得到
  参考文献：
  名称：

  BRUNNER, H.;ZETTLMEIER, W., BULL. SOC. CHIM. BELG., 100,(1991) N, C. 247-257

  摘要：

  DOI：

文献信息

• Brunner, H.; Zettlmeier, W., Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 3, p. 247 - 257
  作者：Brunner, H.、Zettlmeier, W.

  DOI：——

  日期：——
• Substituent Effects of Ligands on Asymmetric Induction in a Prototypical Palladium-Catalyzed Allylation Reaction:  Making Both Enantiomers of a Product in High Optical Purity Using the Same Source of Chirality
  作者：Dean S. Clyne、Yvan C. Mermet-Bouvier、Nobuyoshi Nomura、T. V. RajanBabu

  DOI：10.1021/jo9911387

  日期：1999.10.1

  The substituent effects of the ligands 1 through 8 play a crucial role in determining the enantioselectivity in the palladium-catalyzed asymmetric allylation reaction between 1,3-diphenylprop-2-en-1-yl acetate and the sodium salt of diethyl malonate. For a given chirality of the backbone, electron-deficient and electron-rich ligands generally gave opposite enantiomers, while sterically hindered ligands bad the same enantioselectivity as electron-rich ligands. In the case of flexible backbones with ligands of comparable size, a variation of the enantioselectivity with the electronic properties of the ligand is predictable. In Ligands with rigid backbones, the steric effects of the substituents appear; to play a more decisive role, and caution should be exercised in interpreting the role of electronic effects in such cases. Examples are provided for maximizing both the chemical yield and the enantioselectivity of the allylation reaction through the tuning of the electronic properties of the ligands. In selected cases, the major sense of the asymmetric induction could be reversed solely by changing the electronic properties of the ligands. Bisphosphinites from (R)-(+)-1,1'-bi-2-naphthol (BINOL) can be tuned to produce both (R)- and (S)-products in 80 and 87% ee, respectively. Stoichiometric reaction of complexes 10e* and 10j* with the sodium salt of diethyl malonate gave malonate adducts with enantiomeric excesses in agreement with those obtained under the catalytic conditions. Also reported are the details of an NMR study of the Pd-(eta(3)-1,3-diphenylallyl)bis-diphenylphosphinite and the corresponding bis-dicyclohexylphosphinite complexes 10e* and 10j*.