(E)-6-(3-methoxyphenyl)-5-hexen-1-ol | 128577-62-8

• 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)-6-(3-methoxyphenyl)-5-hexen-1-ol
• 英文别名: (E)-6-(3-methoxyphenyl)hex-5-en-1-ol
• CAS: 128577-62-8
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: OOBBWDKBJDAXEN-QPJJXVBHSA-N

物化性质

• 沸点：
  355.0±35.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-(3-methoxyphenyl)-5-hexen-1-ol 在 甲酸 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-{5-[4-(dimethylaminocarbonyl)butanoylamino]-2-[6-(3-methoxyphenyl)-(5E)-hexenyloxy]phenyl}propanoic acid
  参考文献：
  名称：

  三取代苯白三烯B4受体拮抗剂：合成与构效关系。

  摘要：

  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）。

  DOI：

  10.1016/s0968-0896(97)00089-8
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 lithium aluminium tetrahydride 、 硫酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 (E)-6-(3-methoxyphenyl)-5-hexen-1-ol
  参考文献：
  名称：

  三取代苯白三烯B4受体拮抗剂：合成与构效关系。

  摘要：

  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）。

  DOI：

  10.1016/s0968-0896(97)00089-8

文献信息

• Triethylborane-Mediated Hydrogallation and Hydroindation:  Novel Access to Organogalliums and Organoindiums
  作者：Kazuaki Takami、Satoshi Mikami、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/jo0344790

  日期：2003.8.1

  Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.
• 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.
• 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：——