tert-butyl 3,3,3-trifluoro-2-(hydroxy(phenyl)methyl)propanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: tert-butyl 3,3,3-trifluoro-2-(hydroxy(phenyl)methyl)propanoate
• 英文别名: tert-butyl (2S)-3,3,3-trifluoro-2-[(R)-hydroxy(phenyl)methyl]propanoate
• 化学式: C₁₄H₁₇F₃O₃
• 分子量: 290.282
• InChiKey: GSEDJZBOMDNOKH-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl 3,3,3-trifluoropropanoate 、 苯甲醛 在 C₁₅H₂₂BF₃O₃S 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以87%的产率得到tert-butyl 3,3,3-trifluoro-2-(hydroxy(phenyl)methyl)propanoate
  参考文献：
  名称：

  Bis-exo-2-norbornylboron Triflate for Stereospecific Enolization of 3,3,3-Trifluoropropionates

  摘要：

  The first boron-mediated enolization-aldolization of 3.3,3-Influoropropionates has been reported The preparation and application of bis-exobicyclo[221]heptan-2-ylboron Inflate as a superior reagent for diastereospecific enolization has also been described.

  DOI：

  10.1021/ol1016178

文献信息

• Preparation and application of 2-(arylmethoxy)isopinocampheols for the asymmetric aldol reaction of 3,3,3-trifluoropropionates
  作者：P. Veeraraghavan Ramachandran、Gowrisankar Parthasarathy、Pravin D. Gagare

  DOI：10.1016/j.tetlet.2011.08.034

  日期：2011.10

  The preparation of 2-(arylmethoxy)isopinocampheols from pinanediol via the DIABL-H reduction of the corresponding aryl aldehyde acetals has been described. A systematic examination of the asymmetric aldol reaction of 3,3,3-trifluoropropionates led to the double diastereoselective aldol reaction of 2-(arylmethoxy)isopinocampheyl 3,3,3-trifluoropropionates providing anti-α-trifluoromethyl-β-hydroxy esters

  已经描述了通过DIABL-H还原相应的芳基醛缩醛由pin烷二醇制备2-（芳基甲氧基）异opinocampheols。导致的2-双非对映选择性醛醇缩合反应的3,3,3- trifluoropropionates不对称醛醇缩合反应的系统的检查（芳基甲氧）isopinocampheyl 3,3,3- trifluoropropionates提供抗在63-α三氟甲基β羟基酯–85％的产率、, 99％的抗选择性和80–96％的抗异构体de 。
• B-Chlorodialkylboranes for the enolboration of 3,3,3-trifluoropropionates
  作者：P. Veeraraghavan Ramachandran、Pravin D. Gagare、Gowrisankar Parthasarathy

  DOI：10.1016/j.tetlet.2011.08.159

  日期：2011.11

  The increased acidity of the alpha-protons of 3,3,3-trifluoropropionates was exploited to achieve the enolboration of these esters using dialkylchloroboranes. (C) 2011 Elsevier Ltd. All rights reserved.