(3R)-3-phenyl-3-hydroxybutanoic acid | 36567-70-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (3R)-3-phenyl-3-hydroxybutanoic acid
• 英文别名: (R)-3-hydroxy-3-phenylbutanoic acid；(-)-3-Hydroxy-3-phenyl-buttersaeure；(R)-3-hydroxy-3-phenyl-butyric acid；(R)-3-Hydroxy-3-phenyl-buttersaeure；(3R)-3-hydroxy-3-phenylbutanoic acid
• CAS: 36567-70-1
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: ZCLPSJAOEAKMPO-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-3-phenyl-3-hydroxybutanoic acid 在 Rh on carbon 氢气 作用下， 生成 (R)-3-cyclohexyl-3-hydroxybutyric acid methyl ester
  参考文献：
  名称：

  Asymmetric synthesis of 3-hydroxyacids from aldehyde or dialkyl ketone

  摘要：

  DOI：

  10.1016/s0040-4039(01)84784-5
• 作为产物：
  描述：

  3-hydroxy-3-phenylbutanoic acid 在 吗啡 作用下， 生成 (3R)-3-phenyl-3-hydroxybutanoic acid
  参考文献：
  名称：

  Reid; Turner, Journal of the Chemical Society, 1950, p. 3694

  摘要：

  DOI：

文献信息

• Cu(I)-Catalyzed Hetero-Diels−Alder Reaction between Danishefsky-Type Siloxy Dienes and Ketones
  作者：I-Hon Chen、Kounosuke Oisaki、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ol802134a

  日期：2008.11.20

  A general catalytic method for the hetero-Diels-Alder reaction between Danishefsky-type siloxy dienes and ketones was developed. Optimum results were produced with a catalyst generated from CuOTf x (C6H6)1/2 and TBAT with Ph 3PO as the catalytic additive. This reaction was extended to an asymmetric variant, using a Cu(I)-Walphos catalyst.

  提出了丹尼舍夫斯基型甲硅烷氧基二烯与酮的杂Diels-Alder反应的一般催化方法。使用由CuOTf x（C6H6）1/2和TBAT（Ph 3PO作为催化添加剂）生成的催化剂可获得最佳结果。使用Cu（I）-Walphos催化剂，该反应扩展为不对称变体。
• Enantioselective Synthesis of Boron-Substituted Quaternary Carbon Stereogenic Centers through NHC-Catalyzed Conjugate Additions of (Pinacolato)boron Units to Enones
  作者：Suttipol Radomkit、Amir H. Hoveyda

  DOI：10.1002/anie.201309982

  日期：2014.3.24

  base catalyzed enantioselective boryl conjugate additions (BCAs) that generate products containing boron‐substituted quaternary carbon stereogenic centers are disclosed. Reactions are performed in the presence of 1.0–5.0 mol % of a readily accessible chiral accessible N‐heterocyclic carbene (NHC) and commercially available bis(pinacolato)diboron; cyclic or linear α,β‐unsaturated ketones can be used and

  公开了路易斯碱催化的对映选择性硼基共轭加成 (BCA) 的第一个例子，其产生包含硼取代的季碳立体中心的产物。反应在 1.0–5.0 mol% 的易于获得的手性可接近的 N-杂环卡宾 (NHC) 和市售的双（频哪醇）二硼存在下进行；可以使用环状或线性 α,β-不饱和酮，并且不需要严格排除空气或水分。以 63–95% 的产率和 91:9 至 >99:1 的对映体比率 (er) 获得所需产物。NHC 催化方法的特殊效用在天然产物抗真菌 (-)-crassinervic 酸的对映选择性合成的背景下得到证明。
• Enantioselective synthesis of α- and β-hydroxy acids using -2-phenylcyclohexan-1-ol-as chiral auxiliary
  作者：D. Basavaiah、T.K. Bharathi

  DOI：10.1016/s0040-4039(00)92724-2

  日期：1991.7

  -2-Phenylcyclohexanol has been used as a chiral auxiliary for the preparation of α- and β-hydroxy acids in 85–100% and 11–89% enantiomeric purities respectively.

  -2-苯基环己醇已被用作手性助剂，分别以85-100％和11-89％的对映体纯度制备α-和β-羟基酸。
• The benzene ring as an optically active chromophore—II
  作者：L. Verbit、S. Mitsui、Y. Senda

  DOI：10.1016/0040-4020(66)80046-7

  日期：1966.1

  The optical rotatory dispersion (ORD) of several open chain compounds contaning the benzene chromophore at the asymmetric center has been measured in the UV spectral region. The Cotton effects in the aromatic absorption regions of (−)-methyl 3-hydroxy-3-phenyl-butyrate, (+)-methyl 4-hydroxyl-4-phenylvalerate, (−)-methyl 3-phenylvalerate, and (+)-methyl 3-hydroxy-3-phenylvalerate were too weak to be

  在紫外光谱区中已经测量了几种在不对称中心含有苯生色团的开链化合物的旋光色散（ORD）。棉花在（-）-3-羟基-3-苯基丁酸甲酯，（+）-4-羟基-4-苯基戊酸甲酯，（-）-3-苯基戊酸甲酯和（+）芳香吸收区中的作用3-羟基-3-苯基戊酸-甲酯太弱而不能在操作条件下观察到。但是，（-）-4-苯基戊烷-1,4-二醇和（-）-γ-苯基-γ-戊内酯在260mμ区域均表现出较强的棉花效应。这项工作的结果以及文献中的其他示例表明，开链系统中的芳香棉效应是构象依赖性的。
• New conditions for reactions mediated by yeast
  申请人：Trewhella Arthur Maurice

  公开号：US20050084943A1

  公开（公告）日：2005-04-21

  Organic compounds, such as precursors for aryl ethylamines such as ephedrine, aryl propylamines such as fluoxetine and propionic acid derivatives such as ibuprofen, naproxen and fenoprofen, are subjected to a yeast mediated reduction conducted in the absence of a solvent. The yeast is moistened with water and contacted with the organic compound. The yeast may then be contacted with an organic solvent to dissolve the product of the reaction into the solvent, and a solid/liquid separation used to separate the product from the yeast.

  有机化合物，例如芳基乙胺的前体，如麻黄素，芳基丙胺，如氟西汀和丙酸衍生物，例如布洛芬，萘普生和芬普尼，经过在无溶剂条件下进行的酵母介导还原。酵母被水浸湿并与有机化合物接触。然后可以将有机溶剂与酵母接触，以将反应产物溶解到溶剂中，并使用固液分离将产物与酵母分离。