1-(4-(6-hydroxyhexyl)phenyl)ethan-1-one | 128577-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(6-hydroxyhexyl)phenyl)ethan-1-one
• 英文别名: 6-(4-Acetylphenyl)hexanol；1-[4-(6-hydroxyhexyl)phenyl]ethanone
• CAS: 128577-67-3
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: UDWQAJJVQVVXQO-UHFFFAOYSA-N

物化性质

• 熔点：
  45-46 °C
• 沸点：
  369.4±35.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-(4-(6-hydroxyhexyl)phenyl)ethan-1-one 在 氢氧化钾 、 sodium hydride 、 三乙胺 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 1.5h， 生成 3-[4-[6-(4-Acetylphenyl)hexoxy]-3-(2-carboxyethyl)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 palladium on activated charcoal lithium aluminium tetrahydride 、 三氯化铝 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 8.0h， 生成 1-(4-(6-hydroxyhexyl)phenyl)ethan-1-one
  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

文献信息

• Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides
  作者：Bing-Zhi Chen、Man-Ling Zhi、Chuang-Xin Wang、Xue-Qiang Chu、Zhi-Liang Shen、Teck-Peng Loh

  DOI：10.1021/acs.orglett.8b00441

  日期：2018.4.6

  An efficient method for the preparation of alkyl indium reagents by using unactivated and cheap alkyl chlorides as substrates in the presence of indium and LiI was developed. The thus-formed alkyl indium species effectively underwent palladium-catalyzed cross-coupling reactions with aryl halides with wide functional group tolerance.

  开发了一种通过在铟和LiI存在下使用未活化廉价的烷基氯化物作为底物来制备烷基铟试剂的有效方法。如此形成的烷基铟物种与具有宽泛的官能团耐受性的芳基卤化物有效地经历了钯催化的交叉偶联反应。
• Catalyst-Controlled Diastereoselective Synthesis of Cyclic Amines via C-H Functionalization
  作者：Sailu Munnuri、Adeniyi Michael Adebesin、Mahesh P Paudyal、Muhammed Yousufuddin、Alfonso Dalipe、John R. Falck

  DOI：10.1021/jacs.7b09901

  日期：——

  restrictions, especially in complex molecule synthesis. This report describes a catalyst-controlled regio- and diastereoselective synthesis of N-unprotected pyrrolidines via dirhodium catalyzed intramolecular nitrene insertion into sp3 C-H bonds. The reaction proceeds at rt without external oxidants, nitrene stabilizing groups, or directing functionality. The insights that emerged from the conforma

  由于区分多个相对强的 sp3 CH 键的挑战，这些键的化学行为通常只有细微的差别，因此适用于非活化脂肪族系统的可靠区域和立体化学技术在很大程度上仍然难以捉摸。然而，使用导向基团和/或助剂的方法已经出现，但施加了实际限制，特别是在复杂分子合成中。本报告描述了一种催化剂控制的区域选择性和非对映选择性合成 N-未保护的吡咯烷，通过 dirhodium 催化分子内氮烯插入 sp3 CH 键。反应在室温下进行，无需外部氧化剂、氮烯稳定基团或导向官能团。
• Leukotriene antagonists
  申请人：Eli Lilly and Company

  公开号：US05171882A1

  公开（公告）日：1992-12-15

  This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, intermediates for preparing the derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.

  该发明提供了苯衍生物，它们是白三烯拮抗剂，这些衍生物的配方，用于制备这些衍生物的中间体，以及使用这些衍生物治疗白三烯过度释放引起的疾病的方法。
• Intermediates for leukotriene antagonists
  申请人：Eli Lilly and Company

  公开号：US04992576A1

  公开（公告）日：1991-02-12

  This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, intermediates for preparing the derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.

  本发明提供了苯基衍生物，其为白三烯拮抗剂，这些衍生物的配方，用于制备这些衍生物的中间体，以及使用这些衍生物治疗白三烯过度释放所引起的疾病的方法。
• 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：——