6-(4-methoxyphenyl)hex-5-yn-1-ol | 128599-33-7

• 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: 6-(4-methoxyphenyl)hex-5-yn-1-ol
• CAS: 128599-33-7
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: UQAOKADDXZSSGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  6-(4-methoxyphenyl)hex-5-yn-1-ol 在 Lindlar's catalyst 氢氧化钾 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 1.5h， 生成 3-[3-(2-carboxyethyl)-4-[(Z)-6-(4-methoxyphenyl)hex-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：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 6-(4-methoxyphenyl)hex-5-yn-1-ol
  参考文献：
  名称：

  铂催化的分子内炔烃 OH 和 NH 加成中的区域选择性影响。

  摘要：

  阐明了铂催化的分子内加氢烷氧基化中区域选择性的空间和电子驱动因素。发现了一个分支点，该分支点将过程分为 5-exo 和 6-endo 选择性过程，并且对于两种氧杂环都可以以良好的产率获得烯醇醚。主要影响来自电子效应，其中炔烃取代基诱导炔烃极化，从而导致杂原子优先攻击更缺电子的碳。在其他情况下研究电子效应，包括加氢酰氧基化和加氢胺化，尽管没有统一观察到，但方向性的类似趋势占主导地位。

  DOI：

  10.1021/acs.orglett.9b03557

文献信息

• Catalytic Asymmetric Total Synthesis of (−)-Galanthamine and (−)-Lycoramine
  作者：Lei Li、Qiao Yang、Yuan Wang、Yanxing Jia

  DOI：10.1002/anie.201411338

  日期：2015.5.18

  conceptually new strategy featuring two metal‐catalyzed reactions as the key steps. A new method for the construction of 3,4‐fused benzofurans has been developed through a palladium‐catalyzed intramolecular Larock annulation reaction, which was successfully applied to the construction of the ABD tricyclic skeleton of 1 and 2. To achieve the asymmetric synthesis of 1 and 2, a ScIII/N,N′‐dioxide complex was used

  （-）-加兰他敏（1）和（-）-lycoramine（2）的催化不对称全合成反应已通过采用概念上新颖的策略来实现，该策略以两个金属催化的反应为关键步骤。通过钯催化的分子内Larock环化反应，开发了一种3,4-稠合苯并呋喃的构建新方法，该方法已成功应用于1和2的ABD三环骨架的构建。为了实现1和2的不对称合成，Sc III / N，N'-二氧化物络合物被用来催化3-烷基取代的苯并呋喃酮向甲基乙烯基酮的对映选择性共轭加成反应，以构建手性季碳中心。
• Intramolecular Larock Indole Synthesis: Preparation of 3,4-Fused Tricyclic Indoles and Total Synthesis of Fargesine
  作者：Dong Shan、Yan Gao、Yanxing Jia

  DOI：10.1002/anie.201300571

  日期：2013.4.26

  Core strength: A new and general strategy for the construction of 3,4‐fused tricyclic indoles, which are the core structure of numerous natural products and bioactive molecules, has been developed. The method involves a one‐step intramolecular Larock indolization and was successfully applied to the first total synthesis of fargesine.

  核心强度：已开发出一种新的通用策略，用于构建3,4-稠合的三环吲哚，这是众多天然产物和生物活性分子的核心结构。该方法涉及一步法分子内Larock吲哚化，并已成功地应用于Fargesine的第一个全合成。
• Investigation into the structure–activity relationship of novel concentration dependent, dual action T-type calcium channel agonists/antagonists
  作者：William F. McCalmont、Jaclyn R. Patterson、Michael A. Lindenmuth、Tiffany N. Heady、Doris M. Haverstick、Lloyd S. Gray、Timothy L. Macdonald

  DOI：10.1016/j.bmc.2005.03.004

  日期：2005.6

  This paper describes the synthesis and biological evaluation of a series of straight chain analogs of a compound (1) that was previously synthesized in our research program. These compounds, which are T-type calcium channel antagonists, exhibits potent anti-proliferative activity against a variety of cancer cells. A structure-activity relationship of these analogs against a variety of cancer cells

  本文描述了先前在我们的研究程序中合成的化合物（1）的一系列直链类似物的合成和生物学评估。这些化合物是T型钙通道拮抗剂，对多种癌细胞表现出有效的抗增殖活性。这些类似物与多种癌细胞的构效关系为深入研究该系列化合物的合理药效团提供了见解。此外，这一系列化合物已将自己呈现为一组针对T型钙通道的新型，浓度依赖性，双重作用的激动剂/拮抗剂。
• Ligand-, Copper-, and Amine-Free Sonogashira Reaction of Aryl Iodides and Bromides with Terminal Alkynes
  作者：Sameer Urgaonkar、John G. Verkade

  DOI：10.1021/jo049325e

  日期：2004.8.1

  and amine-free palladium-catalyzed Sonogashira reaction of aryl iodides and bromides with terminal alkynes have been developed. Critical to the success of this new protocol is the use of tetrabutylammonium acetate as the base. Noteworthy features of this method are room-temperature conditions and the tolerance of a broad range of functional groups in both reaction partners.

  已经开发出有效的无配体，无铜和无胺的钯催化的芳基碘化物和溴化物与末端炔烃的Sonogashira反应的条件。该新方案成功的关键是使用乙酸四丁铵作为碱。该方法的显着特征是室温条件和两个反应伙伴中多种官能团的耐受性。
• Step-Economical Synthesis of Taxol-like Tricycles through a Palladium-Catalyzed Domino Reaction
  作者：Julien Petrignet、Aicha Boudhar、Gaëlle Blond、Jean Suffert

  DOI：10.1002/anie.201007751

  日期：2011.3.28

  A quick and easy way to produce tricycles related to the core structure of taxanes has been achieved using a palladium‐catalyzed domino reaction (see scheme, Bz=benzoyl). These studies have been performed with function‐oriented synthesis in mind. An efficient route for the construction of new taxane scaffolds that could be decorated with various groups to achieve activities comparable or superior to

  使用钯催化的多米诺骨牌反应已经实现了一种快速，简便的方法来生产与紫杉烷类核心结构有关的三轮车（参见方案，Bz =苯甲酰基）。进行这些研究时要牢记面向功能的综合。已经提出了一种构建新的紫杉烷支架的有效途径，该新的紫杉烷支架可以用各种基团进行装饰，以实现与紫杉醇相当或更好的活性。