(E)-ethyl 2-fluoro-5-methyl-2-hexenoate | 79695-43-5

• 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 2-fluoro-5-methyl-2-hexenoate
• 英文别名: ethyl (Z)-2-fluoro-5-methylhex-2-enoate
• CAS: 79695-43-5
• 化学式: C₉H₁₅FO₂
• 分子量: 174.215
• InChiKey: NGPUHUOUTLGPJF-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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 2-fluoro-5-methyl-2-hexenoate 在 氢氧化钾 、 水 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以71%的产率得到(E)-2-fluoro-5-methyl-2-hexenoic acid
  参考文献：
  名称：

  Anionic versus photochemical diastereoselective deconjugation of diacetone d-glucose α,β-unsaturated esters

  摘要：

  Deconjugation of diacetone D-glucose alpha, beta-unsaturated esters has been conducted by deprotonation using NaHMDS with HMPA as co-solvent followed by stereoselective protonation at low temperature. High selectivities (>95%) were obtained with oc-methyl linear compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00365-3
• 作为产物：
  描述：

  氯代丙二酸二乙酯 以63%的产率得到
  参考文献：
  名称：

  KITAZUME TOMOYA; ISHIKAWA NOBUO, CHEM. LETT., 1981, NO 9, 1259-1260

  摘要：

  DOI：

文献信息

• Efficient Synthesis of Fluoroalkenes via Diethylzinc-Promoted Wittig Reaction
  作者：Philippe Jubault、Xavier Pannecoucke、Ludivine Zoute、Guillaume Dutheuil、Jean-Charles Quirion

  DOI：10.1055/s-2006-950208

  日期：2006.10

  The synthesis of α-fluoroacrylates and α-bromo-α-fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in the addition sequence was critical in order to obtain exclusively α-fluoroacrylates in good yields.

  α-氟丙烯酸酯和α-溴-α-氟烯烃的合成得到了非常好的产率，使用了醛和酮、三苯基磷、二乙基锌作为促进剂，以及乙基二溴氟乙酸酯或二溴氟甲烷。改变添加顺序对独占性获得α-氟丙烯酸酯的高产率至关重要。
• Diethylzinc-Mediated One-Step Stereoselective Synthesis of α-Fluoroacrylates from Aldehydes and Ketones. Two Different Pathways Depending on the Carbonyl Partner
  作者：G. Lemonnier、L. Zoute、G. Dupas、J.-C. Quirion、P. Jubault

  DOI：10.1021/jo900422m

  日期：2009.6.5

  A efficient methodology allowing the one-pot stereoselective synthesis of alpha-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is described. Two different pathways have been identified depending on the involved carbonyl partner. In the case of aldehydes, an E2-type mechanism has been identified, whereas ketones go through an E1cb-type mechanism.
• Anionic versus photochemical diastereoselective deconjugation of diacetone d-glucose α,β-unsaturated esters
  作者：Frédéric Bargiggia、Olivier Piva

  DOI：10.1016/s0957-4166(03)00365-3

  日期：2003.7

  Deconjugation of diacetone D-glucose alpha, beta-unsaturated esters has been conducted by deprotonation using NaHMDS with HMPA as co-solvent followed by stereoselective protonation at low temperature. High selectivities (>95%) were obtained with oc-methyl linear compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.
• KITAZUME TOMOYA; ISHIKAWA NOBUO, CHEM. LETT., 1981, NO 9, 1259-1260
  作者：KITAZUME TOMOYA、 ISHIKAWA NOBUO

  DOI：——

  日期：——