2-(2-chlorophenyl)pent-4-enoic acid | 619323-31-8

• 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: 2-(2-chlorophenyl)pent-4-enoic acid
• 英文别名: 2-(2-Chlorophenyl)pent-4-enoic acid
• CAS: 619323-31-8
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: XJVKXYASEMVCJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-(2-chlorophenyl)pent-4-enoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 2: structure–activity relationships for substituted 2-aryl-1-[ N -(methyl)- N -(phenylsulfonyl)amino]-4-(piperidin-1-yl)butanes

  摘要：

  (2S)-2-(3,4-二氯苯基)-1-[N-(甲基)-N-(苯基亚砜)氨基]-4-[螺(2,3-二氢苯并噻吩-3,4'-哌啶-1'-基)]丁烷 S-氧化物 (3) 已被鉴定为一种具有强效 CCR5 拮抗活性的先导结构化合物，其 IC50 值为 35 nM。本文中，我们描述了针对 C-2 苯基片段的需求和优化的结构-活性关系研究。研究发现，苯基对于 CCR5 拮抗活性至关重要，取代基仅限于在 3 位引入小型基团（如 13 和 16，当 X=H、3-F、3-Cl、3-Me 时）。(C) 2001 Elsevier Science Ltd. 出版。

  DOI：

  10.1016/s0960-894x(00)00639-9
• 作为产物：
  描述：

  2-氯苯乙酸甲酯 在 lithium hydroxide 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 22.0h， 生成 2-(2-chlorophenyl)pent-4-enoic acid
  参考文献：
  名称：

  Synthesis and structure–antifungal activity Relationships of 3-Aryl-5-alkyl-2,5-dihydrofuran-2-ones and Their Carbanalogues: further refinement of tentative pharmacophore group

  摘要：

  Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00220-7

文献信息

• Oxidative oxygen-nucleophilic bromo-cyclization of alkenyl carbonyl compounds without organic wastes using alkali metal reagents in green solvent
  作者：Katsuhiko Moriyama、Chihiro Nishinohara、Toru Sugiue、Hideo Togo

  DOI：10.1039/c5ra19851h

  日期：——

  developed via the oxidative umpolung of bromide using alkali metal bromide and inorganic oxidant to provide the corresponding cyclization products in high yields. In particular, the use of AcOEt, the solvent of choice for green sustainable reactions, led to the high reactivities of the present reactions. This methodology is highly recommended for green sustainable chemistry because it uses stable and non-hazardous

  通过使用碱金属溴化物和无机氧化剂，通过溴化物的氧化反应，开发了烯基羧酸的溴内酯化和作为氧亲核性溴环化反应的N-烯丙基酰胺的溴环化反应，从而高收率地提供了相应的环化产物。特别地，使用AcOEt，绿色可持续反应的首选溶剂，导致了本反应的高反应性。强烈建议将此方法用于绿色可持续化学，因为它使用稳定且无害的试剂代替其他溴试剂和氧化剂，并且不会产生污染环境的有机废物。
• Synthesis and structure–antifungal activity Relationships of 3-Aryl-5-alkyl-2,5-dihydrofuran-2-ones and Their Carbanalogues: further refinement of tentative pharmacophore group
  作者：Milan Pour、Marcel Špulák、Vojtěch Balšánek、Jiřı́ Kuneš、Petra Kubanová、Vladimı́r Buchta

  DOI：10.1016/s0968-0896(03)00220-7

  日期：2003.7

  Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 2: structure–activity relationships for substituted 2-aryl-1-[ N -(methyl)- N -(phenylsulfonyl)amino]-4-(piperidin-1-yl)butanes
  作者：Paul E Finke、Laura C Meurer、Bryan Oates、Sander G Mills、Malcolm MacCoss、Lorraine Malkowitz、Martin S Springer、Bruce L Daugherty、Sandra L Gould、Julie A DeMartino、Salvatore J Siciliano、Anthony Carella、Gwen Carver、Karen Holmes、Renee Danzeisen、Daria Hazuda、Joseph Kessler、Janet Lineberger、Michael Miller、William A Schleif、Emilio A Emini

  DOI：10.1016/s0960-894x(00)00639-9

  日期：2001.1

  (2S)-2-(3,4-Dichlorophenyl)-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-[spiro(2,3-dihydrobenzthiophene-3,4'-piperidin-1'-yl)]butane S-oxide (3) has been identified as a potent CCR5 antagonist lead structure having an IC50 = 35 nM. Herein, we describe the structure-activity relationship studies directed toward the requirement for and optimization of the C-2 phenyl fragment. The phenyl was found to be important for CCR5 antagonism and substitution was limited to small moieties at the 3-position (13 and 16. X=H, 3-F, 3-Cl, 3-Me). (C) 2001 Published by Elsevier Science Ltd.

  (2S)-2-(3,4-二氯苯基)-1-[N-(甲基)-N-(苯基亚砜)氨基]-4-[螺(2,3-二氢苯并噻吩-3,4'-哌啶-1'-基)]丁烷 S-氧化物 (3) 已被鉴定为一种具有强效 CCR5 拮抗活性的先导结构化合物，其 IC50 值为 35 nM。本文中，我们描述了针对 C-2 苯基片段的需求和优化的结构-活性关系研究。研究发现，苯基对于 CCR5 拮抗活性至关重要，取代基仅限于在 3 位引入小型基团（如 13 和 16，当 X=H、3-F、3-Cl、3-Me 时）。(C) 2001 Elsevier Science Ltd. 出版。