methyl 4-(pent-1-yn-1-yl)benzoate | 1409942-09-1

• 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: methyl 4-(pent-1-yn-1-yl)benzoate
• 英文别名: Methyl 4-pent-1-ynylbenzoate
• CAS: 1409942-09-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: YRQVRDUMUZSLKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-(pent-1-yn-1-yl)benzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 生成 4-戊基苯甲酸甲酯
  参考文献：
  名称：

  Role of the CAI-1 Fatty Acid Tail in the Vibrio cholerae Quorum Sensing Response

  摘要：

  Quorum sensing is a mechanism of chemical communication among bacteria that enables collective behaviors. In V. cholerae, the etiological agent of the disease cholera, quorum sensing controls group behaviors including virulence factor production and biofilm formation. The major V. cholerae quorum-sensing system consists of the extracellular signal molecule called CAI-1 and its cognate membrane bound receptor called CqsS. Here, the ligand binding activity of CqsS is probed with structural analogues of the natural signal. Enabled by our discovery of a structurally simplified analogue of CAI-1, we prepared and analyzed a focused library. The molecules were designed to probe the effects of conformational and structural changes along the length of the fatty acid tail of CAI-1. Our results, combined with pharmacophore modeling, suggest a molecular basis for signal molecule recognition and receptor fidelity with respect to the fatty acid tail portion of CAI-1. These efforts provide novel probes to enhance discovery of antivirulence agents for the treatment of V. cholerae.

  DOI：

  10.1021/jm300908t
• 作为产物：
  描述：

  1-戊炔 、 对溴苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 以95%的产率得到methyl 4-(pent-1-yn-1-yl)benzoate
  参考文献：
  名称：

  Role of the CAI-1 Fatty Acid Tail in the Vibrio cholerae Quorum Sensing Response

  摘要：

  Quorum sensing is a mechanism of chemical communication among bacteria that enables collective behaviors. In V. cholerae, the etiological agent of the disease cholera, quorum sensing controls group behaviors including virulence factor production and biofilm formation. The major V. cholerae quorum-sensing system consists of the extracellular signal molecule called CAI-1 and its cognate membrane bound receptor called CqsS. Here, the ligand binding activity of CqsS is probed with structural analogues of the natural signal. Enabled by our discovery of a structurally simplified analogue of CAI-1, we prepared and analyzed a focused library. The molecules were designed to probe the effects of conformational and structural changes along the length of the fatty acid tail of CAI-1. Our results, combined with pharmacophore modeling, suggest a molecular basis for signal molecule recognition and receptor fidelity with respect to the fatty acid tail portion of CAI-1. These efforts provide novel probes to enhance discovery of antivirulence agents for the treatment of V. cholerae.

  DOI：

  10.1021/jm300908t

文献信息

• Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp³ C–H Activation/Annulation
  作者：Jiuan Zheng、Panpan Li、Meng Gu、Aijun Lin、Hequan Yao

  DOI：10.1021/acs.orglett.7b00930

  日期：2017.6.2

  pyrazolones with alkynes has been developed. This reaction provides a convenient route to synthesize spiropentadiene pyrazolones in good to excellent yields at room temperature, exhibiting good functional group tolerance, gram scalability, and high regioselectivity. Of note, the α-arylidene pyrazolone was introduced as a novel C3 synthon in C–H activation/annulation.

  已经开发了用Rh催化烯醇定向的形式sp 3 C–H活化/环炔基的α-亚芳基吡唑啉酮。该反应提供了在室温下以良好至优异的产率合成螺戊二烯吡唑啉酮的便利途径，表现出良好的官能团耐受性，克可扩展性和高区域选择性。值得注意的是，α-亚芳基吡唑啉酮是在C–H活化/环化反应中作为新型C3合成子引入的。
• Visible‐Light‐Promoted Oxy‐difluoroalkylation of Aryl Alkynes for the Synthesis of <i>β</i> ‐Fluoroenones and <i>α</i> ‐Difluoroalkyl Ketones
  作者：Zhong Zhang、Xiangqian Li、Dayong Shi

  DOI：10.1002/adsc.202100289

  日期：2021.7

  synthesis of (E)-β-fluoroenones and α-difluoroalkyl ketones have been achieved. By employing water as oxygen source, potassium carbonate as base, tetrasubstituted β-fluoroenones could be regio- and stereoselectively synthesized by oxy-difluoroalkylation of alkynes under visible light irradiated with moderate to good yields. α-Difluoroalkyl ketones could be obtained while using phenylpyridine as base

  一种选择性合成( E ) -β-氟烯酮和α-二氟烷基酮的方法已经实现。以水为氧源，碳酸钾为碱，在可见光照射下，炔烃的氧二氟烷基化反应可以区域选择性和立体选择性地合成四取代的β-氟代烯酮，收率适中。以苯基吡啶为碱可制得α-二氟烷基酮。这种改造具有条件温和、功能耐受性广、步骤经济等特点。大规模转化和进一步衍生化显示了其在有机合成中的潜在应用。
• Functionalization of C sp 3H and C sp 2H Bonds: Synthesis of Spiroindenes by Enolate-Directed Ruthenium-Catalyzed Oxidative Annulation of Alkynes with 2-Aryl-1,3-dicarbonyl Compounds
  作者：Suresh Reddy Chidipudi、Imtiaz Khan、Hon Wai Lam

  DOI：10.1002/anie.201207170

  日期：2012.11.26

  Ru(de) awakening: The synthesis of carbocycles by the ruthenium‐catalyzed oxidative annulation of alkynes with 2‐aryl cyclic 1,3‐dicarbonyl substrates is described. Proceeding by the functionalization of CH and CH bonds, and the formation of an all‐carbon quaternary center, the reaction provides a diverse range of spiroindenes in good yields with high levels of regioselectivity.

  Ru（de）唤醒：描述了通过钌催化的炔烃与2-芳基环状1,3-二羰基底物的合成碳环。通过CH和CH键的功能化，以及全碳四元中心的形成，该反应以高收率和高区域选择性提供了多种螺环茚。
• BiCl₃-Mediated direct functionalization of unsaturated C–C bonds with an electrophilic SCF₂PO(OEt)₂ reagent
  作者：Jianjun Wang、Heng-Ying Xiong、Emilie Petit、Laëtitia Bailly、Xavier Pannecoucke、Thomas Poisson、Tatiana Besset

  DOI：10.1039/c9cc01851d

  日期：——

  A transition metal-free approach was developed for the direct difunctionalization of disubstituted alkynes and terminal alkenes with concomitant formation of C–SCF2PO(OEt)2 and C–Cl bonds. The BiCl3-mediated reaction offered access to high value-added functionalized scaffolds in a single operation under mild conditions. Extension to SCF2PO(OEt)2-containing alkynes was also studied.

  开发了一种无过渡金属的方法，用于双取代炔烃和末端烯烃的直接双官能化，并伴随形成C–SCF 2 PO（OEt）2和C–Cl键。BiCl 3介导的反应可在温和的条件下通过一次操作获得高附加值的功能化支架。还研究了向含SCF 2 PO（OEt）2的炔烃的扩展。
• Copper-Catalyzed Azidative Multifunctionalization of Alkynes
  作者：Guangfan Zheng、Jiaqiong Sun、Yang Liu、Shengbiao Yang、Yan Li、Haizhu Sun、Qian Zhang

  DOI：10.1021/acs.joc.7b02148

  日期：2017.12.1

  A facile and efficient copper-catalyzed azidative multifunctionalization of alkynes has been developed by using N-fluorobenzenesulfonimide (NFSI) as both nitrogen source and aryl source and trimethylsilyl azide (TMSN3) as azido source. This transformation proceeds under mild conditions, providing a series of α-azido-α-aryl imine in good yields by a single operation starting from a wide range of alkynes

  通过使用N-氟苯磺酰亚胺（NFSI）作为氮源和芳基源以及三甲基甲硅烷基叠氮化物（TMSN 3）作为叠氮源，已经开发了一种简便有效的炔烃铜催化的叠氮化多官能化方法。该转化在温和的条件下进行，通过从宽范围的炔烃开始的一次操作，以高收率提供了一系列α-叠氮基-α-芳基亚胺。制备的α-叠氮基-α-芳基亚胺可以很容易地转化为1，5-哌嗪稠合的1,2,3-三唑和叠氮基烯胺。