methyl 2-(1-naphthyl)-4-pentenoate | 93434-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-(1-naphthyl)-4-pentenoate
• 英文别名: methyl 2-(1-naphthyl)pent-4-enoate；(+/-)-2--penten-(4)-saeure-(1)-methylester；(+/-)-2-(Naphthyl-(1))-penten-(4)-saeure-(1)-methylester
• CAS: 93434-05-0
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: ZZQRCWGFJYYJJO-UHFFFAOYSA-N

物化性质

• 沸点：
  338.2±11.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(1-naphthyl)-4-pentenoate 在 lithium hydroxide 、 正丁基锂 、 苯基氯化硒 、 硫酸 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.33h， 生成 2-methyl-4-(1-naphthyl)-2H-furan-5-one
  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
• 作为产物：
  描述：

  1-萘乙酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 methyl 2-(1-naphthyl)-4-pentenoate
  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

• Copper(I)-Catalyzed Borylative <i>exo</i>-Cyclization of Alkenyl Halides Containing Unactivated Double Bond
  作者：Koji Kubota、Eiji Yamamoto、Hajime Ito

  DOI：10.1021/ja3104582

  日期：2013.2.20

  A borylative exo-cyclization of alkenyl halides has been reported. The reaction includes the regioselective addition of a borylcopper(I) intermediate to unactivated terminal alkenes, followed by the intramolecular substitution of the resulting alkylcopper(I) moiety for the halide leaving groups. Experimental and theoretical investigations of the reaction mechanism have also been described. This reaction

  已经报道了烯基卤化物的硼酸化外环化。该反应包括将硼基铜 (I) 中间体区域选择性加成到未活化的末端烯烃，然后将所得烷基铜 (I) 部分分子内取代为卤化物离去基团。还描述了反应机理的实验和理论研究。该反应为从简单的原料合成含有应变环烷基结构的烷基硼酸酯提供了一种新方法。
• Tandem Pd-Catalyzed Carbonylation and Intramolecular Vinyl Allene Diels−Alder Reaction toward Galiellalactone Analogues
  作者：Ritha Gidlöf、Martin Johansson、Olov Sterner

  DOI：10.1021/ol101989m

  日期：2010.11.19

  A novel route toward new galiellalactone analogues via a tandem palladium-catalyzed carbonylation and intramolecular Diels−Alder reaction of a dienyne carbonate is presented.

  通过串联钯催化的羰基化反应和碳酸二烯炔的分子内Diels-Alder反应，提出了一种新的新的galiellalactone类似物的途径。
• Szarvasi; Bayssat; Fontaine, Bulletin de la Societe Chimique de France, 1966, vol. 6, p. 1838 - 1846
  作者：Szarvasi、Bayssat、Fontaine、Grand

  DOI：——

  日期：——