1-(4-methoxyphenyl)-2-fluoroethyl alcohol | 40733-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenyl)-2-fluoroethyl alcohol
• 英文别名: (+/-)-2-fluoro-1-(4-methoxyphenyl)ethanol；2-Fluoro-1-(4-methoxyphenyl)ethan-1-ol；2-fluoro-1-(4-methoxyphenyl)ethanol
• CAS: 40733-98-0
• 化学式: C₉H₁₁FO₂
• 分子量: 170.184
• InChiKey: UHGXYHMFGJAKMX-UHFFFAOYSA-N

物化性质

• 沸点：
  285.0±35.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-2-fluoroethyl alcohol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以75%的产率得到1-(4-methoxyphenyl)-2-fluoroethyl chloride
  参考文献：
  名称：

  Richard, John P.; Amyes, Tina L.; Bei, Li, Journal of the American Chemical Society, 1990, vol. 112, # 26, p. 9513 - 9519

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氟-1-(4-甲氧基苯基)乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 1-(4-methoxyphenyl)-2-fluoroethyl alcohol
  参考文献：
  名称：

  Synthesis of Enantiopure Fluorohydrins Using Alcohol Dehydrogenases at High Substrate Concentrations

  摘要：

  The use of purified and overexpressed alcohol dehydrogenases to synthesize enantiopure fluorinated alcohols is shown. When the bioreductions were performed with ADH-A from Rhodococcus ruber overexpressed in E. coli, no external cofactor was necessary to obtain the enantiopure (R)-derivatives. Employing Lactobacillus brevis ADH, it was possible to achieve the synthesis of enantiopure (S)-fluorohydrins at a 0.5 M substrate concentration. Furthermore, due to the activated character of these substrates, a huge excess of the hydrogen donor was not necessary.

  DOI：

  10.1021/jo400962c

文献信息

• α-Fluoromethyl-n-methyl-phenylsulphoximine: a new fluoromethylenation reagent
  作者：Mark L. Boys、Eric W. Collington、Harry Finch、Stephen Swanson、John F. Whitehead

  DOI：10.1016/0040-4039(88)85163-3

  日期：1988.1

  Treatment of aldehydes or ketones with the anion derived from α-fluoromethyl--methyl-phenylsulphoximine produces adducts which afford fluoro-olefins on reductive elimination.

  用衍生自α-氟代甲基-甲基-苯基亚砜基亚胺的阴离子处理醛或酮产生加合物，该加合物在还原消除时提供氟代烯烃。
• Stavber, Stojan; Pecan, Tjasa Sotler; Zupan, Marko, Journal of the Chemical Society. Perkin transactions II, 2000, # 6, p. 1141 - 1146
  作者：Stavber, Stojan、Pecan, Tjasa Sotler、Zupan, Marko

  DOI：——

  日期：——
• Asymmetric reduction using (R)-MeCBS and determination of absolute configuration of para-substituted 2-fluoroarylethanols
  作者：Erik Fuglseth、Eirik Sundby、Per Bruheim、Bård Helge Hoff

  DOI：10.1016/j.tetasy.2008.07.019

  日期：2008.8

  The asymmetric reduction of eight alpha-fluoroacetophenones has been investigated using (R)-MeCBS as a catalyst in various media. Based on a solvent screen, 1,2-dimethoxyethane, diethyl ether and dichloromethane were used in reductions of the alpha-fluoroacetophenones. The enantiomeric excess of the products depended oil the solvent and the electronic character of the aromatic substituents. Higher enantioselectivity and less solvent dependency were observed in the reduction of substrates bearing electron donating substituents, whereas the opposite was the case for reduction of the substrates with electron withdrawing substituents. The (R)-2-fluoro-1-arylethanols were obtained with enantiomeric excesses in the range of 91-99% using 1,2-dimethoxyethane as a solvent. Six of the alcohols produced are new chemical entities. The absolute configurations of the (R)-2-fluoro-1-arylethanols were determined by circular dichroism using the exciton chirality method of tile (S)-benzoate esters of the alcohols. The (S)-benzoate esters were obtained by lipase-catalysed resolution using Novozym 435. (C) 2008 Elsevier Ltd. All Fights reserved.
• BOYS, MARK L.;COLLINGTON, ERIC W.;FINCH, HARRY;SWANSON, STEPHEN;WHITEHEAD+, TETRAHEDRON LETT., 29,(1988) N 27, 3365-3368
  作者：BOYS, MARK L.、COLLINGTON, ERIC W.、FINCH, HARRY、SWANSON, STEPHEN、WHITEHEAD+

  DOI：——

  日期：——
• Synthesis of Enantiopure Fluorohydrins Using Alcohol Dehydrogenases at High Substrate Concentrations
  作者：Wioleta Borzęcka、Iván Lavandera、Vicente Gotor

  DOI：10.1021/jo400962c

  日期：2013.7.19

  The use of purified and overexpressed alcohol dehydrogenases to synthesize enantiopure fluorinated alcohols is shown. When the bioreductions were performed with ADH-A from Rhodococcus ruber overexpressed in E. coli, no external cofactor was necessary to obtain the enantiopure (R)-derivatives. Employing Lactobacillus brevis ADH, it was possible to achieve the synthesis of enantiopure (S)-fluorohydrins at a 0.5 M substrate concentration. Furthermore, due to the activated character of these substrates, a huge excess of the hydrogen donor was not necessary.