methanesulfonate of 6-phenyl-(5E)-hexenol | 197707-45-2

• 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: methanesulfonate of 6-phenyl-(5E)-hexenol
• 英文别名: 6-phenylhex-5-en-1-yl methanesulfonate；[(E)-6-phenylhex-5-enyl] methanesulfonate
• CAS: 197707-45-2
• 化学式: C₁₃H₁₈O₃S
• 分子量: 254.35
• InChiKey: CQYAZKACBPGRFS-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methanesulfonate of 6-phenyl-(5E)-hexenol 在 氢氧化钾 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 3-[3-(2-carboxyethyl)-4-[(E)-6-phenylhex-5-enoxy]benzoyl]benzoic 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：

  4-羧丁基三苯基溴化膦 在 lithium aluminium tetrahydride 、 硫酸 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 methanesulfonate of 6-phenyl-(5E)-hexenol
  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

• Aminolithiation–arylation consecutive cyclization of N-(2-fluorophenyl)methylaminoalkylstyryls giving aryl-substituted pyrido[1,2-b]isoquinolines
  作者：Yasutomo Yamamoto、Yasue Nakanishi、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2018.05.085

  日期：2018.9

  Aminolithiation-arylation tandem cyclization of N-(2-fluorophenyl)methylaminoalkylstyryls proceeded smoothly to give hexahydro-2H-pyrido[1,2-b]isoquinoline using a stoichiometric amount of n-BuLi with high trans selectivity. The arylation reaction was highly accelerated by the addition of HMPA. Both pyrido- and pyrrolo-[1,2-b]isoquinoline were successfully constructed by this tandem reaction. (C) 2018 Elsevier Ltd. All rights reserved.
• 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：——