2-fluoro-but-3-en-1-ol | 151021-54-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2-fluoro-but-3-en-1-ol
• 英文别名: 2-fluoro-3-buten-1-ol；2-fluorobut-3-en-1-ol
• CAS: 151021-54-4
• 化学式: C₄H₇FO
• 分子量: 90.0974
• InChiKey: BVGFHDJXKIXOAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  129.3±25.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  联苯乙醛 、 2-fluoro-but-3-en-1-ol 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到
  参考文献：
  名称：

  Monofluorinated di- and tetrahydropyrans via Prins-type cyclisations

  摘要：

  通过路易斯酸介导的 Prins 型环化描述了一系列氟化杂环的合成。

  DOI：

  10.1039/b606121d
• 作为产物：
  描述：

  环氧丁烯 在 triethylamine trihydrogen fluoride 作用下， 反应 8.0h， 以58%的产率得到2-fluoro-but-3-en-1-ol
  参考文献：
  名称：

  乙烯基水合物三氟乙胺三氟乙酰胺

  摘要：

  在温和的条件下，三乙胺三氟化氢对乙烯基环氧乙烷的作用导致相应的氟化均烯丙基醇。这些醇中的一些是不稳定的，因此已经转化为相应的更稳定的甲苯磺酸酯。

  DOI：

  10.1016/0022-1139(94)03104-8

文献信息

• Rhodium-catalyzed regioselective opening of vinyl epoxides with Et₃N·3HF reagent – formation of allylic fluorohydrins
  作者：Qi Zhang、Hien M. Nguyen

  DOI：10.1039/c3sc51949j

  日期：——

  A highly regioselective rhodium-catalyzed ring-opening of vinyl epoxides with Et3N·3HF reagent to form branched allylic fluorohydrins is described. The reaction occurs at room temperature under ambient air and relies on RhCOD2BF4 as an effective catalyst, providing the desired 1,2-addition allylic fluorohydrins in moderate to good yields with excellent levels of regioselectivity. Mechanistic studies

  描述了具有高区域选择性的铑催化的乙烯基环氧化物与Et 3 N·3HF试剂的开环反应，以形成支链烯丙基氟代醇。该反应在室温下在环境空气下进行，并且依赖于RhCOD 2 BF 4作为有效催化剂，以中等至良好的产率提供所需的1,2-加成的烯丙基氟代醇，并具有极好的区域选择性。机理研究表明，对映体纯乙烯基环氧化物的区域选择性开环是随着立体化学的反转而发生的。
• On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
  作者：Freda K. Chio、Julie Warne、Damien Gough、Mark Penny、Sasa Green (née Martinović)、Simon J. Coles、Mike B. Hursthouse、Peter Jones、Lorraine Hassall、Thomas M. McGuire、Adrian P. Dobbs

  DOI：10.1016/j.tet.2011.05.019

  日期：2011.7

  While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reaction of homoallylic alcohols, and two new modifications of the reaction: the triflate-trapped Prins adduct and the Mukaiyama-Aldol-silyl-Prins reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (+/-)-Civet. (C) 2011 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of an All-<i>syn</i> Four Vicinal Fluorine Motif
  作者：Luke Hunter、David O'Hagan、Alexandra M. Z. Slawin

  DOI：10.1021/ja066188p

  日期：2006.12.1

  Alkanes bearing multiple vicinal fluorine atoms at adjacent stereocenters may be considered intermediate between alkanes and perfluoroalkanes, and as a class, their chemistry and behavior remain to be explored. We report here a stereoselective synthesis of an all-syn four vicinal fluorine motif as a single enantiomer. The four vicinal fluorine compound was amenable to single-crystal X-ray analysis, and the resulting structure displays gauche relationships between all four fluorines, consistent with the fluorine gauche effect, and CF...HC hydrogen bonding between adjacent fluoroalkyl chains.
• Synthesis of 2-fluoro-3-buten-1-ol
  作者：C.Y. Robinson、V. John

  DOI：10.1016/s0022-1139(00)80101-3

  日期：1993.6

  The synthesis of the previously unreported alcohol, 2-fluoro-3-buten-1-ol (1), was accomplished by the reaction of butadiene monoxide with pyridinium poly(hydrogen fluoride). Alcohol 1 was obtained as a mixture with pyridine after distillation. Direct use of the pyridine/fluoroalcohol mixture for reaction with t-butyldiphenylsilyl (TBDPS) chloride gave the silyl ether which was readily purified by silica gel chromatography. Ozonolysis of the silyl ether gave the corresponding fluoroaldehyde. The procedure described offers a useful route to 1 and its derivatives.
• Ouverture des vinyloxiranes par le fluorhydrate de triéthylamine triacide
  作者：A. Hedhli、A. Baklouti

  DOI：10.1016/0022-1139(94)03104-8

  日期：1995.1

  The action of triethylamine trihydrogen fluoride on vinyloxiranes leads, under mild conditions, to the corresponding fluorinated homoallylic alcohols. Some of these alcohols are unstable and accordingly have been converted into the corresponding more stable tosylates.

  在温和的条件下，三乙胺三氟化氢对乙烯基环氧乙烷的作用导致相应的氟化均烯丙基醇。这些醇中的一些是不稳定的，因此已经转化为相应的更稳定的甲苯磺酸酯。