(R)-2-(β-naphthyloxy)propionic acid | 25153-08-6

• 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-(β-naphthyloxy)propionic acid
• 英文别名: (R)-2-(2-naphthoxy)propanoic acid；2-(2-naphthyloxy)propanoic acid；(R)-O-(2-naphthyl)lactic acid；(R)-2-[2]naphthyloxy-propionic acid；(R)-2-[2]Naphthyloxy-propionsaeure；(R)-2-(Naphthalen-2-yloxy)propanoic acid；(2R)-2-naphthalen-2-yloxypropanoic acid
• CAS: 25153-08-6
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: HMIVVAPMRQMNAK-SECBINFHSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  389.7±15.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  (R)-2-(β-naphthyloxy)propionic acid 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 3.5h， 生成 (R)-ipsdienyl (R)-2-(β-naphthyloxy)propionate
  参考文献：
  名称：

  Tottie, Louise; Moberg, Christina; Heumann, Andreas, Acta Chemica Scandinavica, 1993, vol. 47, # 5, p. 492 - 499

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 辛可宁 作用下， 生成 (R)-2-(β-naphthyloxy)propionic acid
  参考文献：
  名称：

  Fourneau; Balaceano, Bulletin de la Societe Chimique de France, 1925, vol. <4> 37, p. 1607

  摘要：

  DOI：

文献信息

• Determination of the Absolute Configuration of Amines and α-Amino Acids by ¹H NMR of (<i>R</i>)-<i>O</i>-Aryllactic Acid Amides
  作者：Rafael Chinchilla、Larry R. Falvello、Carmen Nájera

  DOI：10.1021/jo9604191

  日期：1996.1.1

  (R)-O-Aryllactic acid (ROAL) amides derived from alpha-chiral primary amines and alpha-amino acid esters show different chemical shifts in (1)H NMR spectroscopy (300 MHz) depending on their configuration. Molecular mechanics, semiempirical calculations, and (1)H NMR studies suggest that, in solution, these amides prefer an ap-Z conformation with the C(alpha)OAr and C=O groups close to anti-periplanar

  衍生自α-手性伯胺和α-氨基酸酯的（R）-O-丙烯酸（ROAL）酰胺根据其构型在（1）H NMR光谱（300 MHz）中显示不同的化学位移。分子力学，半经验计算和（1）H NMR研究表明，在溶液中，这些酰胺更喜欢ap-Z构象，其中CαOOAr和C = O基团与反平面相似，类似于扁桃体。酰胺。所提出的构象偏好不同于ROAL酯的构象偏好（在顺周构象中为CαH和C ＝ O基团）。ROAL酰胺的构象模型允许根据芳基和胺部分上的取代基的相对位置以及它们的对映体组成，对伯胺和α-氨基酸酯进行绝对构型分配。
• Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates
  作者：Surrinder Koul、Jawahir Lal Koul、Budh Singh、Munish Kapoor、Rajinder Parshad、Kuldeep S. Manhas、Subhash C. Taneja、Ghulam N. Qazi

  DOI：10.1016/j.tetasy.2005.07.009

  日期：2005.8

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.
• Fredga; Matell, Arkiv foer Kemi, 1952, vol. 3, p. 429,431
  作者：Fredga、Matell

  DOI：——

  日期：——
• 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).