(E)-6-(4-fluorophenyl)hex-5-enoic acid | 128577-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-6-(4-fluorophenyl)hex-5-enoic acid
• 英文别名: 6-(4-Fluorophenyl)hex-5-enoic acid
• CAS: 128577-57-1
• 化学式: C₁₂H₁₃FO₂
• 分子量: 208.232
• InChiKey: OJRASBZJVPSDHV-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-(4-fluorophenyl)hex-5-enoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 1.0h， 以79%的产率得到6-(4-fluorophenyl)hexanoic acid
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotaxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils. Activity at the LTB4 receptor was determined by using a [3H]LTB4-binding assay. The structure-activity relationship for the lipophilic side chain was systematically investigated. Compounds with n-alkyl side chains of varying lengths were prepared and tested. Best inhibition of [3H]LTB4 binding was observed with the n-decyl derivative. Analogues with alkyl chains terminated with an aromatic ring showed improved activity. The 6-phenylhexyl side chain was optimal. Substitution on the terminal aromatic ring was also evaluated. Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound. For a given substituent, the para isomer had the best activity. Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils. The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with an affinity approaching that of the agonist.

  DOI：

  10.1021/jm00172a020
• 作为产物：
  描述：

  环戊酮 在 三氟甲磺酸 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 环己烷 为溶剂， 反应 1.5h， 生成 (E)-6-(4-fluorophenyl)hex-5-enoic acid
  参考文献：
  名称：

  通过环烷酮缩酮的位点特异性活化实现芳香羰基的烯化**

  摘要：

  简单的底物设计允许环酮的位点特异性活化，用于芳香族羰基化合物的烯化反应。

  DOI：

  10.1002/anie.202317003

文献信息

• Lewis base-catalyzed asymmetric sulfenylation of alkenes: construction of sulfenylated lactones and application to the formal syntheses of (−)-nicotlactone B and (−)-galbacin
  作者：Hui-Yun Luo、Yu-Yang Xie、Xu-Feng Song、Jia-Wei Dong、Deng Zhu、Zhi-Min Chen

  DOI：10.1039/c9cc04758a

  日期：——

  5-endo and 6-exo thiolactonizations of alkenes. Two types of lactones were obtained with up to 95% ee and 99% yield. Additionally, this methodology has been applied in the formal syntheses of bioactive natural products (−)-nicotlactone B and (−)-galbacin.

  基于不饱和羧酸的路易斯碱催化的对映选择性亚磺酰基化，已经描述了制备手性亚磺酰基化内酯的有效方法。该方法的范围包括两个对映选择性环化反应：烯烃的5-内硫基和6-外硫醇内酯化。获得了两种类型的内酯，它们的ee高达95％，产率高达99％。此外，该方法已应用于生物活性天然产物（-）-烟酰胺内酯B和（-）-半乳糖苷的正式合成中。
• GAPINSKI, D. MARK;MALLETT, BARBARA E.;FROELICH, LARRY L.;JACKSON, WILLIAM+, J. MED. CHEM., 33,(1990) N0, C. 2807-2813
  作者：GAPINSKI, D. MARK、MALLETT, BARBARA E.、FROELICH, LARRY L.、JACKSON, WILLIAM+

  DOI：——

  日期：——
• Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain
  作者：D. Mark Gapinski、Barbara E. Mallett、Larry L. Froelich、William T. Jackson

  DOI：10.1021/jm00172a020

  日期：1990.10

  A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotaxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils. Activity at the LTB4 receptor was determined by using a [3H]LTB4-binding assay. The structure-activity relationship for the lipophilic side chain was systematically investigated. Compounds with n-alkyl side chains of varying lengths were prepared and tested. Best inhibition of [3H]LTB4 binding was observed with the n-decyl derivative. Analogues with alkyl chains terminated with an aromatic ring showed improved activity. The 6-phenylhexyl side chain was optimal. Substitution on the terminal aromatic ring was also evaluated. Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound. For a given substituent, the para isomer had the best activity. Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils. The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with an affinity approaching that of the agonist.
• Olefination of Aromatic Carbonyls via Site‐Specific Activation of Cycloalkanone Ketals**
  作者：Tuong Anh To、Thanh Vinh Nguyen

  DOI：10.1002/anie.202317003

  日期：2024.1.2

  A simple substrate design allows site-specific activation of cyclic ketones for olefination reaction of aromatic carbonyl compounds.

  简单的底物设计允许环酮的位点特异性活化，用于芳香族羰基化合物的烯化反应。