(E)-6-(p-tolyl)hex-5-enoic acid | 128577-58-2

• 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-(p-tolyl)hex-5-enoic acid
• 英文别名: (E)-6-(4-methylphenyl)hex-5-enoic acid
• CAS: 128577-58-2
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: FGKXECNXBWHPGZ-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-(p-tolyl)hex-5-enoic acid 在 lithium aluminium tetrahydride 、 sodium hydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 ethyl 3-[3-(3-ethoxy-3-oxopropyl)-4-[(E)-6-(4-methylphenyl)hex-5-enoxy]benzoyl]benzoate
  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-(p-tolyl)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

• Trisubstituted benzene leukotriene B4 receptor antagonists: Synthesis and structure-activity relationships
  作者：Mitoshi Konno、Takahiko Nakae、Shigeru Sakuyama、Yoshihiko Odagaki、Hisao Nakai、Nobuyuki Hamanaka

  DOI：10.1016/s0968-0896(97)00089-8

  日期：1997.8

  A series of trisubstituted benzenes which demonstrate leukotriene B4 (LTB4, 1) receptor affinity was prepared. Previous trisubstituted benzenes from our laboratory showed high affinity to the LTB4 receptor but demonstrated agonist activity in functional assays. Compound 3a, the initial lead compound of this new series, showed only modest affinity (IC50 = 0.20 microM). However, 3a was a receptor antagonist

  制备了一系列显示白三烯B4（LTB4，1）受体亲和力的三取代苯。我们实验室以前的三取代苯对LTB4受体显示出高亲和力，但在功能测定中显示出激动剂活性。该新系列的初始前导化合物化合物3a仅表现出适度的亲和力（IC50 = 0.20 microM）。但是，3a是一种受体拮抗剂，在高达30 microM时没有明显的激动剂活性。脂质尾部和芳基头部区域的进一步修饰导致3b（ONO-4057）的发现。该化合物无激动剂活性，对LTB4受体具有高亲和力（Ki = 3.7 +/- 0.9 nM）。
• Hydrogen Atom Transfer (HAT)-Mediated Remote Desaturation Enabled by Fe/Cr–H Cooperative Catalysis
  作者：Yanjun Wan、Augustine K. Adda、Jin Qian、David A. Vaccaro、Peixian He、Gang Li、Jack R. Norton

  DOI：10.1021/jacs.3c13085

  日期：2024.2.21

  An iron/chromium system (Fe(OAc)2, CpCr(CO)3H) catalyzes the preparation of β,γ- or γ,δ-unsaturated amides from 1,4,2-dioxazol-5-ones. An acyl nitrenoid iron complex seems likely to be responsible for C–H activation. A cascade of three H• transfer steps appears to be involved: (i) the abstraction of H• from a remote C–H bond by the nitrenoid N, (ii) the transfer of H• from Cr to N, and (iii) the abstraction

  铁/铬体系（Fe(OAc) 2 、CpCr(CO) 3 H）催化从1,4,2-二恶唑-5-酮制备β,γ-或γ,δ-不饱和酰胺。酰基氮烯类铁络合物似乎可能负责 C-H 激活。似乎涉及三个 H• 转移步骤的级联：(i) 通过氮素 N 从远程 C-H 键中提取 H•，(ii) H• 从 Cr 转移到 N，以及 (iii)由Cr•从自由基取代基中抽象出H•。如果氮烯类化合物的形成是速率决定步骤，则观察到的动力学同位素效应与所提出的机制一致。 Fe/Cr 催化剂还可以将取代的 1,4,2-二恶唑-5-酮去饱和为 3,5-二烯酰胺。
• 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。