(2Z)-2-fluoro-3-(4-fluorophenyl)-2-propen-1-ol | 1221508-34-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2Z)-2-fluoro-3-(4-fluorophenyl)-2-propen-1-ol
• 英文别名: (Z)-2-fluoro-3-(4-fluorophenyl)-2-propan-1-ol；(Z)-2-fluoro-3-(4-fluorophenyl)prop-2-en-1-ol
• CAS: 1221508-34-4
• 化学式: C₉H₈F₂O
• 分子量: 170.159
• InChiKey: AGRFHVYZLCAGTM-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z)-2-fluoro-3-(4-fluorophenyl)-2-propen-1-ol 在 正丁醇 作用下， 反应 48.0h， 生成 (S)-2-fluoro-3-(4-fluorophenyl)-propanol 、 (R)-2-fluoro-3-(4-fluorophenyl)-propanol
  参考文献：
  名称：

  Highly enantioselective bioreduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae

  摘要：

  Biocatalytic reduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae was investigated in phosphate buffer solutions. Product analysis clearly showed that (S)-2-fluoro-3-arylpropanols were afforded in high yields with up to 92% ee Value. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.01.073
• 作为产物：
  描述：

  对氟肉桂醛 在 甲醇 、 sodium tetrahydroborate 、 sodium acetate 、 Selectfluor 、 L-脯氨酸 作用下， 以 硝基甲烷 为溶剂， 反应 21.5h， 生成 (2Z)-2-fluoro-3-(4-fluorophenyl)-2-propen-1-ol
  参考文献：
  名称：

  一锅 l -脯氨酸介导的立体选择性 α-C(sp2 )-H 通过甲氧基氟化消除 α,β-不饱和醛的氟化

  摘要：

  已经开发出一锅两步 L-脯氨酸介导的立体选择性 α-C(sp2)-H 将 α,β-不饱和醛氟化为其相应的 (Z)-α-氟-α,β-不饱和醛. 第一步使用 Selectfluor 作为 CH3NO2/MeOH 中的氟化剂，通过甲氧基氟化消除形成 (Z)-α-氟-α,β-不饱和醛及其相应的二甲基缩醛。在第二步中，加入水以促进二甲基缩醛的水解裂解。所得(Z)-α-氟-α,β-不饱和醛被NaBH4平滑还原为相应的醇。

  DOI：

  10.1002/ejoc.201700622

文献信息

• An efficient access to (Z)-β-fluoroallyl alcohols based on the two carbon homologation of aromatic aldehydes by Horner–Wadsworth–Emmons reaction with 2-(diethoxyphosphinyl)-2-fluoro-ethanethioic acid, S-ethyl ester followed by reduction with sodium borohydride
  作者：Mohammed Kajjout、Rajae Zemmouri、Said Eddarir、Christian Rolando

  DOI：10.1016/j.tet.2012.02.039

  日期：2012.4

  approach to (Z)-β-fluoroallyl alcohols based on the two carbon homologation of aromatic aldehydes to α-fluorocinnamic thioesters by Horner–Wadsworth–Emmons reaction with 2-(diethoxyphosphinyl)-2-fluoro-ethanethioic acid, S-ethyl ester, followed by reduction with sodium borohydride in mild conditions. The α-fluorothioesters were obtained in a good yield by condensing the aldehydes with the lithium anion of

  我们描述了一种仿生方法（Z）-β-氟代烯丙醇，其基于霍纳-沃兹沃思-埃蒙斯与2-（二乙氧基膦基）-2-氟代-乙硫基酸S的芳香醛到α-氟代肉桂酸酯的两个碳同系物-乙基酯，然后在温和条件下用硼氢化钠还原。通过将醛与2-（二乙氧基膦基）-2-氟-乙硫酸锂，S-乙酯的锂阴离子在-78°C的THF中缩合，可以以高收率获得α-氟代硫酯。然后将（E，Z）-α-氟肉桂酸硫代酯混合物通过双键异构化通过NaBH 4干净地还原为相应的（Z）-β-氟烯丙基醇在室温下。该方法可以应用于高度官能化的醛，例如可以直接获得（Z）-β-氟松柏油，这是一种从O-糖基化香兰素木质素聚合的强抑制剂。
• Palladium-Catalyzed Stereoconvergent Formylation of (<i>E</i>/<i>Z</i>)-β-Bromo-β-fluorostyrenes: Straightforward Access to (<i>Z</i>)-α-Fluorocinnamic Aldehydes and (<i>Z</i>)-β-Fluorocinnamic Alcohols
  作者：Rajae Zemmouri、Mohammed Kajjout、Yves Castanet、Said Eddarir、Christian Rolando

  DOI：10.1021/jo200798h

  日期：2011.10.7

  We report here the stereoconvergent formylation of (E/Z)-beta-bromo-beta-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-alpha-fluorocinnamaldehydes in good yields. The reaction was extended to styrenes bearing electro-attracting or electro-donating groups. The obtained alpha-fluoroaldehydes were smoothly reduced to the corresponding (Z)-beta-fluorocinnamic alcohol by NaBH4. The reaction could be performed on functionalized substrates as demonstrated by the access to the glucoside of beta-fluoroconiferyl alcohol, (Z)-beta-fluoroconiferin, a strong inhibitor of lignin polymerization.
• One-Pot <scp>l</scp> -Proline-Mediated Stereoselective α-C(sp² )-H Fluorination of α,β-Unsaturated Aldehydes through Methoxyfluorination-Elimination
  作者：Jiadi Zhou、Xinpeng Jiang、Can Jin、Zhicheng Guo、Bin Su、Weike Su

  DOI：10.1002/ejoc.201700622

  日期：2017.7.7

  of α,β-unsaturated aldehydes to their corresponding (Z)-α-fluoro-α,β-unsaturated aldehydes has been developed. The first step utilises Selectfluor as a fluorinating agent in CH3NO2/MeOH forming (Z)-α-fluoro-α,β-unsaturated aldehydes and their corresponding dimethyl acetals via methoxyfluorination-elimination. In the second step, water is added to promote the hydrolytic cleavage of the dimethyl acetals

  已经开发出一锅两步 L-脯氨酸介导的立体选择性 α-C(sp2)-H 将 α,β-不饱和醛氟化为其相应的 (Z)-α-氟-α,β-不饱和醛. 第一步使用 Selectfluor 作为 CH3NO2/MeOH 中的氟化剂，通过甲氧基氟化消除形成 (Z)-α-氟-α,β-不饱和醛及其相应的二甲基缩醛。在第二步中，加入水以促进二甲基缩醛的水解裂解。所得(Z)-α-氟-α,β-不饱和醛被NaBH4平滑还原为相应的醇。
• Highly enantioselective bioreduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae
  作者：Fan Luo、Ping Wang、Yuefa Gong

  DOI：10.1016/j.tetlet.2010.01.073

  日期：2010.3

  Biocatalytic reduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae was investigated in phosphate buffer solutions. Product analysis clearly showed that (S)-2-fluoro-3-arylpropanols were afforded in high yields with up to 92% ee Value. (C) 2010 Published by Elsevier Ltd.