(E)-Ethyl 3-hexyl-2-fluoropropenate | 32814-15-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-Ethyl 3-hexyl-2-fluoropropenate
• 英文别名: (E)-ethyl 2-fluoro-2-nonenoate；ethyl (E)-2-fluoronon-2-enoate
• CAS: 32814-15-6
• 化学式: C₁₁H₁₉FO₂
• 分子量: 202.269
• InChiKey: OCTKFGWMCQSSLZ-MDZDMXLPSA-N

物化性质

• 沸点：
  243.9±15.0 °C(predicted)
• 密度：
  0.952±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-Ethyl 3-hexyl-2-fluoropropenate 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.83h， 生成 (E)-diethyl 2-fluoro-2-nonen-1-ylphosphate
  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：

  庚醛 、 2-氟-2-磷酰基乙酸三乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (E)-Ethyl 3-hexyl-2-fluoropropenate
  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

文献信息

• Stereoselective formation of (Z)-2-fluoroalkenoates via Julia–Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones
  作者：Florent Larnaud、Emmanuel Pfund、Bruno Linclau、Thierry Lequeux

  DOI：10.1016/j.tet.2014.06.081

  日期：2014.9

  This sulfone allowed the preparation of Z-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle on the course of the Julia–Kocienski reaction is discussed.

  从嘧啶基氟砜报道了氟代链烯酸酯的选择性合成。该砜允许由芳族和脂族醛两者制备具有非常高的立体选择性的Z-氟代链烯酸酯。讨论了Julia-Kocienski反应过程中杂环的性质。
• Preparation of fluorinated alkenes in ionic liquids
  作者：Tomoya Kitazume、Genji Tanaka

  DOI：10.1016/s0022-1139(00)00331-6

  日期：2000.12

  The utility of ionic liquids (8-ethyl-1,8-diazabicyclo[5,4,0]-7-undecene trifluoromethanesulfonate and 8-methyl-1,8-diazabicydo[5,4,0]7-undecene trifluoromethanesulfonate) as a safe: recyclable reaction medium for the synthesis of alpha -fluoro-alpha,beta -unsaturated esters by the Horner-Wadsworth-Emmons reaction with aldehydes in the presence of base, is described. (C) 2000 Elsevier Science S.A. All rights reserved.
• 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.