(R)-2-[(1,1'-biphenyl)-2-yloxy]propanoic acid | 133775-02-7

• 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: (R)-2-[(1,1'-biphenyl)-2-yloxy]propanoic acid
• 英文别名: (R)-2-(2-phenylphenoxy)propionic acid；(2R)-2-(2-phenylphenoxy)propanoic acid
• CAS: 133775-02-7
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: LHACJRMZSJGCFY-LLVKDONJSA-N

物化性质

• 沸点：
  378.6±17.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-1,2-divinylocyclohexane 、 (R)-2-[(1,1'-biphenyl)-2-yloxy]propanoic acid 在 manganese(IV) oxide 、 palladium diacetate 、 对苯醌 作用下， 以 丙酮 为溶剂， 生成 (1R,6S,7S)-7-<<((R)-1-(2-phenylphenoxy)ethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane 、 (1S,6R,7R)-7-<<((R)-1-(2-phenylphenoxy)ethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane
  参考文献：
  名称：

  Molecular sieve controlled diastereoselectivity: effect in the palladium-catalyzed cyclization of cis-1,2-divinylcyclohexane with .alpha.-oxygen-substituted acids as chiral nucleophiles

  摘要：

  Molecular sieves have been shown to improve greatly the stereoselectivity in the palladium(II)-catalyzed reaction of cis-1,2-divinylcyclohexane with chiral acids. Reactions run with molecular sieves and derivatives of (R)-lactic acids as nucleophiles always yielded products with S configuration at the newly formed chiral center in contrast to reactions without molecular sieves that gave products with either S or R configuration at this chiral center. It appears that this effect has not been observed previously. Only water-containing molecular sieves increased the stereoselectivity. A chiral palladium complex was formed faster in the presence of molecular sieves, but use of this complex as catalyst in the cyclization did not result in increased selectivity. The best stereoselectivity was found for molecular sieves with a high sodium content (Lancaster 13X and 4-angstrom sieves).

  DOI：

  10.1021/jo00050a039
• 作为产物：
  描述：

  ethyl (2R)-2-(2-phenylphenoxy)propanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-2-[(1,1'-biphenyl)-2-yloxy]propanoic acid
  参考文献：
  名称：

  Molecular sieve controlled diastereoselectivity: effect in the palladium-catalyzed cyclization of cis-1,2-divinylcyclohexane with .alpha.-oxygen-substituted acids as chiral nucleophiles

  摘要：

  Molecular sieves have been shown to improve greatly the stereoselectivity in the palladium(II)-catalyzed reaction of cis-1,2-divinylcyclohexane with chiral acids. Reactions run with molecular sieves and derivatives of (R)-lactic acids as nucleophiles always yielded products with S configuration at the newly formed chiral center in contrast to reactions without molecular sieves that gave products with either S or R configuration at this chiral center. It appears that this effect has not been observed previously. Only water-containing molecular sieves increased the stereoselectivity. A chiral palladium complex was formed faster in the presence of molecular sieves, but use of this complex as catalyst in the cyclization did not result in increased selectivity. The best stereoselectivity was found for molecular sieves with a high sodium content (Lancaster 13X and 4-angstrom sieves).

  DOI：

  10.1021/jo00050a039

文献信息

• A New Method for Production of Chiral 2-Aryloxypropanoic Acids Using Effective Kinetic Resolution of Racemic 2-Aryloxycarboxylic Acids
  作者：Isamu Shiina、Atsushi Tengeiji、Kenya Nakata、Keisuke Ono

  DOI：10.3987/com-12-s(n)79

  日期：——

  We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv(2)O) as an activating agent, bis(alpha-naphthyl)methanol ((alpha-Np)(2)CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.
• Molecular sieve controlled diastereoselectivity: effect in the palladium-catalyzed cyclization of cis-1,2-divinylcyclohexane with .alpha.-oxygen-substituted acids as chiral nucleophiles
  作者：Louise Tottie、Peter Baeckstroem、Christina Moberg、Joergen Tegenfeldt、Andreas Heumann

  DOI：10.1021/jo00050a039

  日期：1992.11

  Molecular sieves have been shown to improve greatly the stereoselectivity in the palladium(II)-catalyzed reaction of cis-1,2-divinylcyclohexane with chiral acids. Reactions run with molecular sieves and derivatives of (R)-lactic acids as nucleophiles always yielded products with S configuration at the newly formed chiral center in contrast to reactions without molecular sieves that gave products with either S or R configuration at this chiral center. It appears that this effect has not been observed previously. Only water-containing molecular sieves increased the stereoselectivity. A chiral palladium complex was formed faster in the presence of molecular sieves, but use of this complex as catalyst in the cyclization did not result in increased selectivity. The best stereoselectivity was found for molecular sieves with a high sodium content (Lancaster 13X and 4-angstrom sieves).