2-fluoro-2-phenylpropanol | 120400-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-fluoro-2-phenylpropanol
• 英文别名: 2-fluoro-2-phenyl-propan-1-ol；2-Fluoro-2-phenylpropan-1-ol
• CAS: 120400-88-6
• 化学式: C₉H₁₁FO
• 分子量: 154.184
• InChiKey: SNILNSRRYODOMT-UHFFFAOYSA-N

物化性质

• 沸点：
  241.5±20.0 °C(predicted)
• 密度：
  1.081±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：

  2-fluoro-2-phenylpropanol 在 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 ethyl (E)-4-fluoro-4-phenylpent-2-enoate
  参考文献：
  名称：

  Synthesis of γ-Fluoro-α, β-unsaturated Carboxylic Esters from Saturated α-Fluoro Aldehydes

  摘要：

  gamma-Fluoro-alpha,beta-unsaturated carboxylic esters 7a, 7b and 7d and 4-fluoro-4-phenylbut-3-enoic ester (8) are obtained by two alternative pathways from 2-fluoro aldehydes 5a-d, either by Horner-Wadsworth-Emmons reaction or by Wittig reaction. The aldehydes 5a-d are prepared by Swern oxidation of the corresponding fluorohydrins 4a-d. These are available from alpha-olefins by bromofluorination, bromine-by-acetate replacement and subsequent hydrolysis.

  DOI：

  10.1002/(sici)1521-3897(200001)342:1<52::aid-prac52>3.0.co;2-h
• 作为产物：
  描述：

  (1-溴-2-氟-2-丙基)苯 在 氢氧化钾 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.25h， 生成 2-fluoro-2-phenylpropanol
  参考文献：
  名称：

  Synthesis of γ-Fluoro-α, β-unsaturated Carboxylic Esters from Saturated α-Fluoro Aldehydes

  摘要：

  gamma-Fluoro-alpha,beta-unsaturated carboxylic esters 7a, 7b and 7d and 4-fluoro-4-phenylbut-3-enoic ester (8) are obtained by two alternative pathways from 2-fluoro aldehydes 5a-d, either by Horner-Wadsworth-Emmons reaction or by Wittig reaction. The aldehydes 5a-d are prepared by Swern oxidation of the corresponding fluorohydrins 4a-d. These are available from alpha-olefins by bromofluorination, bromine-by-acetate replacement and subsequent hydrolysis.

  DOI：

  10.1002/(sici)1521-3897(200001)342:1<52::aid-prac52>3.0.co;2-h

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。
• Fluorination with ionic liquid EMIMF(HF)2.3 as mild HF source
  作者：Hideaki Yoshino、Kazuhiko Matsumoto、Rika Hagiwara、Yasuhiko Ito、Koichiro Oshima、Seijiro Matsubara

  DOI：10.1016/j.jfluchem.2005.09.016

  日期：2006.1

  Hydrogen fluoride is a basic fluorinating reagent, but handling it is difficult. For this reason, some modified fluorinating reagents such as HF-pyridine, Et3N-HF, and poly(hydrogen fluoride) complex have been developed. Those reagents, however, still require aqueous work-up procedures which generate hydrogen fluoride. Recently, ionic liquids have received much attention because of the ease in handling

  氟化氢是一种基本的氟化试剂，但是处理起来很困难。为此，已经开发了一些改性的氟化试剂，例如HF-吡啶，Et 3 N-HF和聚（氟化氢）络合物。但是，这些试剂仍需要进行水溶液后处理程序，以产生氟化氢。近来，由于易于处理和非水后处理的可能性，离子液体受到了广泛的关注。在空气和湿气中稳定的离子液体3-乙基-1-甲基咪唑鎓低聚氟化氢（EMIMF（HF）2.3）可以用作某些氟化反应的氟化氢当量；它不需要水后处理。
• Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage
  作者：Kazutaka Shibatomi、Kazumasa Kitahara、Takuya Okimi、Yoshiyuki Abe、Seiji Iwasa

  DOI：10.1039/c5sc03486h

  日期：——

  The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst.

  高度对映选择性氟化α-支链醛利用新开发的手性初级胺催化剂实现。
• (Salen)chromium Complex Mediated Asymmetric Ring Opening of meso- and Racemic Epoxides with Different Fluoride Sources
  作者：Günter Haufe、Stefan Bruns

  DOI：10.1002/1615-4169(200202)344:2<165::aid-adsc165>3.0.co;2-1

  日期：2002.2

  as cyclopentene oxide and cycloheptene oxide the corresponding fluorohydrins were isolated in 80% and 82% yield with 65% and 62% ee, respectively. In case of ring opening under similar conditions of the racemic styrene oxide or phenyl glycidyl ether 83% and 75% of the fluorohydrins with fluorine in the primary position were isolated with 74% ee and 65% ee, respectively. Tetrahydronaphthalene oxide yielded

  在化学计量或化学计量稍低的雅各布森对映纯（salen）氯化铬络合物A存在下，用不同的氟化试剂对五个内消旋和三个外消旋环氧化物进行不对称开环，得到了相应的旋光性邻位氟代醇。氟化银被用作氟化物来源之一无论是在卜存在4 Ñ + ħ 2 ˚F 3 -在乙醚或乙腈。从氧化环己烯（起始后者反应1）显示出在所形成的最大fluorohydrin 72％ee的2以90％的产率分离。从其他介观-环氧化合物，例如环戊烯氧化物和环庚烯氧化物，分离相应的氟代醇，产率分别为80％和82％，ee分别为65％和62％。在外消旋的苯乙烯氧化物或苯基缩水甘油醚的类似条件下开环的情况下，分别以74％ee和65％ee分离出83％和75％的氟醇，其中氟位于主要位置。四氢萘氧化物产生反式-（23％ee）和顺式-2-氟-3,4-苯并环己烯醇（2％ee）的2：1混合物，表明存在竞争的S N 2和S N 1型开环。其他环氧化物，例如环辛烯