(R)-(-)-4'-methoxy-3-phenylbutyric acid | 4974-05-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-(-)-4'-methoxy-3-phenylbutyric acid
• 英文别名: (3R)-3-(4-methoxyphenyl)butanoic acid；(R)-3-(4-methoxyphenyl)butanoic acid；3-(4-methoxyphenyl)butanoic acid；(-)-(3R)-3-(4-Methoxy-phenyl)-buttersaeure
• CAS: 4974-05-4
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: GTUSGMFEBAENPL-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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)-(-)-4'-methoxy-3-phenylbutyric acid 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟甲磺酸二丁硼 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.42h， 生成 (R)-3-[(2S,3S)-2-Bromo-3-(4-methoxy-phenyl)-butyryl]-4-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  Efficient method for the total asymmetric synthesis of the isomers of .beta.-methyltyrosine

  摘要：

  Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale asymmetric syntheses of the isomers are needed. A method for the stereoselective large-scale synthesis of an four stereoisomers of beta-methyltyrosine is described in this paper. The stereochemistry of both the alpha- and beta-stereocenters was set using 4-phenyl-2-oxazolidinone as a chiral auxiliary. The key reactions were an asymmetric Michael-like addition of an organocuprate to a chiral alpha,beta-unsaturated acyloxazolidinone (beta center) and subsequent stereoselective electrophilic bromination of the resulting product (alpha center). Conversion of the bromide to the azide, catalyzed hydrolysis to the azido acid with simultaneous recovery of the chiral auxiliary, reduction of the azide, and final deprotection of the phenol group afforded the desired amino acids. In general, the reactions were performed in yields over 80 %, and the isomers were obtained in enantiomeric purities of 98:2 to 99:1.

  DOI：

  10.1021/jo00078a042
• 作为产物：
  描述：

  (3(3R),4S)-3-<3-(4'-Methoxyphenyl)butanoyl>-4-phenyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以90%的产率得到(R)-(-)-4'-methoxy-3-phenylbutyric acid
  参考文献：
  名称：

  Asymmetric 1,4-addition of organocuprates to chiral .alpha.,.beta.-unsaturated N-acyl-4-phenyl-2-oxazolidinones: a new approach to the synthesis of chiral .beta.-branched carboxylic acids

  摘要：

  DOI：

  10.1021/jo00055a039

文献信息

• Asymmetric synthesis of unusual amino acids: Synthesis of optically pure isomers of β-methyltyrosine
  作者：Ernesto Nicolas、Ramalinga Dharanipragada、Geza Toth、Victor J Hruby

  DOI：10.1016/s0040-4039(01)93367-2

  日期：1989.1

  Synthesis of optically pure isomers of β-methyltyrosine has been accomplished.

  β-甲基酪氨酸的光学纯异构体的合成已经完成。
• Stereoselective Carbon−Carbon Bond Formation via the Mitsunobu Displacement of Chiral Secondary Benzylic Alcohols
  作者：Michael C. Hillier、Jean-Nicolas Desrosiers、Jean-François Marcoux、Edward J. J. Grabowski

  DOI：10.1021/ol036380l

  日期：2004.2.1

  [reaction: see text] The stereoselective displacement of a variety of chiral benzylic alcohols with triethylmethanetricarboxylate (TEMT) under Mitsunobu conditions (DEAD, PMe(3)) has been demonstrated to proceed in good yield (70-94%) and with a high degree of inversion. Subsequent saponification and decarboxylation of the products thus obtained provide chiral 3-aryl-3-substituted propanoic acids without

  [反应：见正文]在Mitsunobu条件下（DEAD，PMe（3））用三乙基三羧酸三乙酯（TEMT）立体选择性置换各种手性苄醇已证明收率高（70-94％），且收率高。反转程度。由此获得的产物的随后的皂化和脱羧提供了手性的3-芳基-3-取代的丙酸而没有外消旋化。
• Determination of the enantiomeric excesses of chiral acids by 19F NMR studies of their esters deriving from (R)-(+)-2-(trifluoromethyl)benzhydrol
  作者：Eric Brown、Christelle Chevalier、François Huet、Christelle Le Grumelec、Antoine Lézé、Joël Touet

  DOI：10.1016/0957-4166(94)80154-1

  日期：1994.7

  15 Chiral acids were esterified with optically pure (R)-(+)-2-(trifluoromethyl)benzhydrol (R)-(+)-1, a readily available reagent. With respect to the carboxy group, the stereogenic centre is in the beta position in the case of the acids 5a-10a and 12a-16a, and in the alpha position in the case of the acids 17a-20a. The diastereomeric excesses of the corresponding esters 5b-10b and 12b-20b, respectively, were easily determined by means of F-19 NMR. These d.e. values were in very good agreement with the e.e. values of the corresponding acids when the latter were known compounds.
• Lipase catalysed kinetic resolutions of 3-aryl alkanoic acids
  作者：Rebecca E. Deasy、Maude Brossat、Thomas S. Moody、Anita R. Maguire

  DOI：10.1016/j.tetasy.2010.12.019

  日期：2011.1

  Hydrolase catalysed kinetic resolutions leading to a series of 3-aryl alkanoic acids (>= 94% ee) are described. Hydrolysis of the ethyl esters with a series of hydrolases was undertaken to identify biocatalysts that yield the corresponding acids with excellent enantiopurity in each case. Steric and electronic effects on the efficiency and enantioselectivity of the biocatalytic transformation were also explored. (C) 2011 Elsevier Ltd. All rights reserved.
• Rh-Catalyzed Highly Enantioselective Synthesis of 3-Arylbutanoic Acids
  作者：Xianfeng Sun、Le Zhou、Chun-Jiang Wang、Xumu Zhang

  DOI：10.1002/anie.200604810

  日期：2007.4.2