(E)-2-fluoro-3-(4-methoxyphenyl)-2-propen-1-ol | 830-02-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-2-fluoro-3-(4-methoxyphenyl)-2-propen-1-ol
• 英文别名: (E)-2-fluoro-3-(4-methoxyphenyl)prop-2-en-1-ol
• CAS: 830-02-4
• 化学式: C₁₀H₁₁FO₂
• 分子量: 182.195
• InChiKey: DWYWKQKDWNNSDO-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (E)-2-fluoro-3-(4-methoxyphenyl)-2-propen-1-ol 在 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.66h， 生成 2-fluoro-3-(4-methoxyphenyl)-1-heptene
  参考文献：
  名称：

  Highly regioselective SN2′ reaction of β-fluoroallylic phosphates with organocopper reagents and its application to the synthesis of fluorine-containing carbocycles

  摘要：

  Treatment of beta-fluoroallyl phosphates with 2.2 equiv. of organocuprates, prepared readily from 2.2 equiv. each of CuCN and organometallics (organolithium reagents, Grignard reagents, and organozinc reagents), in THF at -40 to 0 degrees C for 0.25 to 24 h gave gamma-products in a highly regioselective manner. Thus obtained gamma-adducts were subjected to the ring-closing metathesis, the corresponding cyclic fluoroalkenes being afforded in good yields. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.06.012
• 作为产物：
  描述：

  2-fluoro-3-(4-methoxyphenyl)acrylic acid ethyl ester 在 二异丁基氢化铝 、 Rochelle salt 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以80%的产率得到(E)-2-fluoro-3-(4-methoxyphenyl)-2-propen-1-ol
  参考文献：
  名称：

  Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae

  摘要：

  Biocatalytic reduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae underwent smoothly and yielded (S)-2-fluorinated alkanols with high enantioselectivities. The conversion rate was markedly depending on the configuration of alkene moiety of the substrate, the chain length of alkyl group at beta position of C=C bond, as well as the reaction conditions. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.02.011

文献信息

• A New Route for the Synthesis of Mono-fluorinated Allyl Alcohols Using the Stereoselective Wittig Olefination via Reaction of (α-flurovinyl)triphenylphosphonium Triflate
  作者：Takeshi Hanamoto、Kazusa Nishiyama、Hiroki Tateishi、Michio Kondo

  DOI：10.1055/s-2001-16070

  日期：——

  The three-component coupling reaction of (α-fluorovinyl)triphenylphosphonium triflate, cesium allylate, and aldehydes in trimethyl orthoformate gave the corresponding mono-fluorinated allyl ethers with good stereoselectivity; the resulting ethers were readily transformed into the corresponding mono-fluorinated allyl alcohols using the Cp2Zr-mediated reaction.

  在原甲酸三甲酯中，(δ-氟乙烯基)三苯基鏻、烯丙基铯和醛的三组分偶联反应具有良好的立体选择性，可得到相应的单氟化烯丙基醚；利用 Cp2Zr 介导的反应，很容易将得到的醚转化为相应的单氟化烯丙基醇。
• Highly regioselective SN2′ reaction of β-fluoroallylic phosphates with organocopper reagents and its application to the synthesis of fluorine-containing carbocycles
  作者：Takashi Nihei、Yusuke Kubo、Takashi Ishihara、Tsutomu Konno

  DOI：10.1016/j.jfluchem.2014.06.012

  日期：2014.11

  Treatment of beta-fluoroallyl phosphates with 2.2 equiv. of organocuprates, prepared readily from 2.2 equiv. each of CuCN and organometallics (organolithium reagents, Grignard reagents, and organozinc reagents), in THF at -40 to 0 degrees C for 0.25 to 24 h gave gamma-products in a highly regioselective manner. Thus obtained gamma-adducts were subjected to the ring-closing metathesis, the corresponding cyclic fluoroalkenes being afforded in good yields. (C) 2014 Elsevier B.V. All rights reserved.
• Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae
  作者：Fan Luo、Dengfu Lu、Yuefa Gong

  DOI：10.1016/j.molcatb.2011.02.011

  日期：2011.7

  Biocatalytic reduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae underwent smoothly and yielded (S)-2-fluorinated alkanols with high enantioselectivities. The conversion rate was markedly depending on the configuration of alkene moiety of the substrate, the chain length of alkyl group at beta position of C=C bond, as well as the reaction conditions. (C) 2011 Elsevier B.V. All rights reserved.