(RS,RS)-1-氟-1-苯基丙烷-2-醇 | 3451-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (RS,RS)-1-氟-1-苯基丙烷-2-醇
• 英文名称: (RS,RS)-1-fluoro-1-phenylpropan-2-ol
• 英文别名: (1S,2S)-1-fluoro-1-phenylpropan-2-ol
• CAS: 3451-41-0；3451-42-1；90416-80-1；114181-12-3
• 化学式: C₉H₁₁FO
• 分子量: 154.184
• InChiKey: AAAFRBMMBSPWKX-IONNQARKSA-N

物化性质

• 沸点：
  236.3±20.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS,RS)-1-氟-1-苯基丙烷-2-醇 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  β-Fluoroamphetamines via the Stereoselective Synthesis of Benzylic Fluorides

  摘要：

  A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3 center dot OEt2 in CH2Cl2 at -20 degrees C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S(N)1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted beta-fluoroamphetamines.

  DOI：

  10.1021/ol100862s
• 作为产物：
  描述：

  1-苯基-1,2-环氧丙烷 在 三氟化硼乙醚 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以83%的产率得到(RS,RS)-1-氟-1-苯基丙烷-2-醇
  参考文献：
  名称：

  β-Fluoroamphetamines via the Stereoselective Synthesis of Benzylic Fluorides

  摘要：

  A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3 center dot OEt2 in CH2Cl2 at -20 degrees C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S(N)1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted beta-fluoroamphetamines.

  DOI：

  10.1021/ol100862s

文献信息

• Potassium dihydrogen trifluoride: a novel fluorinating reagent for ring-opening of epoxides
  作者：Masanori Tamura、Motonari Shibakami、Takashi Arimura、Shigeru Kurosawa、Akira Sekiya

  DOI：10.1016/0022-1139(94)03175-y

  日期：1995.1

  It has been found that potassium dihydrogen trifluoride is an efficient and easy-to-handle solid reagent for the ring-opening reaction of epoxides giving fluorohydrins regio- and stereo-selectively. The reaction proceeds via cis-addition of HF to the epoxide.

  已经发现，三氟化二氢钾是一种有效且易于处理的固体试剂，用于环氧化物和立体选择性地产生氟代醇的环氧化物的开环反应。该反应通过将HF顺式加成到环氧化物上而进行。
• Highly selective ring opening of epoxides with silicon tetrafluoride: Preparation of fluorohydrins
  作者：Makoto Shimizu、Hirosuke Yoshioka

  DOI：10.1016/s0040-4039(00)80427-x

  日期：1988.1

  Regio-, stereo-, and chemoselective transformation of epoxides into fluorohydrins with silicon tetrafluoride is described.

  描述了用四氟化硅将环氧的区域，立体和化学选择性转化为氟代醇。
• Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides
  作者：Alexander J. Cresswell、Stephen G. Davies、Aude L.A. Figuccia、Ai M. Fletcher、Dorus Heijnen、James A. Lee、Melloney J. Morris、Alice M.R. Kennett、Paul M. Roberts、James E. Thomson

  DOI：10.1016/j.tetlet.2014.12.044

  日期：2015.6

  The incorporation of alkoxy ligands within a range of alkoxyfluoroboranes and dialkoxyfluoroboranes results in fluoroborane reagents with attenuated Lewis acidity and increased ability to donate fluoride ion(s) when compared to boron trifluoride itself. Pinacolatoboron fluoride (pinBF), prepared in situ from BF3 center dot OEt2 and bis(O-trimethylsilyl)pinacol, has been identified as an efficient fluoride donor which allows highly stereoselective S(N)1-type epoxide ring-opening (with retention of configuration) of a range of trans-beta-methyl-substituted aryl epoxides to give the corresponding syn-fluorohydrins. The substrate scope of this transformation is more broad than the analogous protocol using boron trifluoride alone. (C) 2014 Elsevier Ltd. All rights reserved.
• Ring-opening fluorination of epoxides using hydrofluoric acid and additives
  作者：Makoto Shimizu、Yuko Nakahara

  DOI：10.1016/s0022-1139(99)00180-3

  日期：1999.11

  Epoxides underwent ring-opening fluorination reaction with hydrofluoric acid in the presence of silicon fluorides and additives to give fluorohydrines in good yields. (C) 1999 Elsevier Science S.A. All rights reserved.
• BRAVO, PIERFRANCESCO;PIOVOSI, ELENA;RESNATI, GUISEPPE, J. CHEM. RES. (S),(1989) N, C. 134-135
  作者：BRAVO, PIERFRANCESCO、PIOVOSI, ELENA、RESNATI, GUISEPPE

  DOI：——

  日期：——