2-(4-Carboxyphenyl)-vinyl-1-ethylcyclopropylketon | 56359-01-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(4-Carboxyphenyl)-vinyl-1-ethylcyclopropylketon
• 英文别名: 2-(4-Carboxyphenyl)vinyl 1-ethylcyclopropyl ketone；4-[3-(1-ethylcyclopropyl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 56359-01-4
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: JBNMFTZMQPBHPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Carboxyphenyl)-vinyl-1-ethylcyclopropylketon 在 lithium aluminium tetrahydride 作用下， 生成 2-(4-Carboxyphenyl)-ethyl-1-ethylcyclopropylcarbinol
  参考文献：
  名称：

  Antiviral activity of some .beta.-diketones. 1. Aryl alkyl diketones. In vitro activity against both RNA and DNA viruses

  摘要：

  The discovery that 4-[3-ethyl-6-[(3,4-methylenedioxy)phenyl]-3-hexenyl]-3,5-heptanedione (40) exhibited an in vitro inhibitory effect against equine rhinovirus led to a structure--activity study to establish the criteria for optimum activity. Modification of the bridge included removal of the ethyl group and reduction of the double bond. The heptanedione was replaced with hexanedione and pentanedione with a minimal effect. The effect of replacing the heptanedione with beta-keto esters and monoketones was also investigated. Maintaining the hexamethylene bridge and heptanedione, the methylenedioxy group was replaced with various substitutents. In general, most substituents did not adversely affect activity particularly against equine rhinovirus although there was some variation in activity against herpesvirus. Strongly hydrophilic groups significantly reduced activity. Finally, the effect of varying the length of the alkyl bridge was examined in the 4-hydroxyphenyl series, where peak activity was attained with n = 8.

  DOI：

  10.1021/jm00216a003
• 作为产物：
  描述：

  1-(1-乙基环丙基)乙酮 、 对醛基苯甲酸 在 sodium hydroxide 作用下， 生成 2-(4-Carboxyphenyl)-vinyl-1-ethylcyclopropylketon
  参考文献：
  名称：

  Antiviral activity of some .beta.-diketones. 1. Aryl alkyl diketones. In vitro activity against both RNA and DNA viruses

  摘要：

  The discovery that 4-[3-ethyl-6-[(3,4-methylenedioxy)phenyl]-3-hexenyl]-3,5-heptanedione (40) exhibited an in vitro inhibitory effect against equine rhinovirus led to a structure--activity study to establish the criteria for optimum activity. Modification of the bridge included removal of the ethyl group and reduction of the double bond. The heptanedione was replaced with hexanedione and pentanedione with a minimal effect. The effect of replacing the heptanedione with beta-keto esters and monoketones was also investigated. Maintaining the hexamethylene bridge and heptanedione, the methylenedioxy group was replaced with various substitutents. In general, most substituents did not adversely affect activity particularly against equine rhinovirus although there was some variation in activity against herpesvirus. Strongly hydrophilic groups significantly reduced activity. Finally, the effect of varying the length of the alkyl bridge was examined in the 4-hydroxyphenyl series, where peak activity was attained with n = 8.

  DOI：

  10.1021/jm00216a003

文献信息

• Dialkylaminophenylethyl (or vinyl) cyclopropyl carbinols
  申请人：Sterling Drug Inc.

  公开号：US04166074A1

  公开（公告）日：1979-08-28

  Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine. The invention herein claimed relates to intermediate arylethyl cyclopropyl carbinols and arylvinyl cyclopropyl carbinols wherein aryl is phenyl substituted by dialkylamino.

  取代芳基二酮和酮基酯，可用作抗病毒剂和杀虫剂，通过将芳基烷基或芳基烯基碘化物与适当的二酮或酮基酯金属盐反应制备而成。中间体碘化物通过将甲基环丙酮与芳香醛缩合制备而成，以得到芳基乙基环丙基醇或芳基乙烯基环丙基醇，用三溴化磷和溴化锌处理醇，以得到芳基烷基或芳基烯基溴化物，然后再将溴原子替换为碘。所述发明涉及中间体芳基乙基环丙基醇和芳基乙烯基环丙基醇，其中芳基为苯基，被二烷基氨基取代。
• Aryl substituted diketones
  申请人：Sterling Drug Inc.

  公开号：US04171378A1

  公开（公告）日：1979-10-16

  Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester.

  含有芳基取代的二酮和酮酯，可用作抗病毒剂和杀虫剂，通过将芳基烷基或芳基烯基碘化物与适当的二酮或酮酯的金属盐反应制备。
• Arylvinyl cyclopropyl ketones
  申请人：Sterling Drug Inc.

  公开号：US04182729A1

  公开（公告）日：1980-01-08

  Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.

  芳基取代的二酮和酮酯，可用作抗病毒剂和杀虫剂，通过将芳基烷基或芳基烯基碘化物与适当的二酮或酮酯的金属盐反应制备而成。中间产物碘化物通过将甲基环丙酮与芳香醛缩合得到芳基乙烯基环丙酮，还原后得到芳基乙基环丙基醇或芳基乙烯基环丙基醇，用三溴化磷处理醇，然后用溴化锌处理，得到芳基烷基或芳基烯基溴化物，然后用碘代替溴原子。
• Substituted phenylvinyl cyclopropyl ketones
  申请人：Sterling Drug Inc.

  公开号：US04227015A1

  公开（公告）日：1980-10-07

  Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.

  芳基取代的二酮和酮酯可用作抗病毒剂和杀虫剂，通过将芳基烷基或芳基烯基碘化物与适当的二酮或酮酯金属盐反应制备而成。中间产物碘化物通过将甲基环丙酮与芳香醛缩合，得到芳基乙烯基环丙酮，将后者还原为芳基乙基环丙醇或芳基乙烯基环丙醇，用三溴化磷处理醇，然后用溴化锌处理，得到芳基烷基或芳基烯基溴化物，最后用碘代替溴原子。
• Antiviral activity of some .beta.-diketones. 1. Aryl alkyl diketones. In vitro activity against both RNA and DNA viruses
  作者：Guy D. Diana、U. Joseph Salvador、Ethel S. Zalay、Robert E. Johnson、Joseph C. Collins、David Johnson、William B. Hinshaw、Roman R. Lorenz、William H. Thielking、Francis Pancic

  DOI：10.1021/jm00216a003

  日期：1977.6

  The discovery that 4-[3-ethyl-6-[(3,4-methylenedioxy)phenyl]-3-hexenyl]-3,5-heptanedione (40) exhibited an in vitro inhibitory effect against equine rhinovirus led to a structure--activity study to establish the criteria for optimum activity. Modification of the bridge included removal of the ethyl group and reduction of the double bond. The heptanedione was replaced with hexanedione and pentanedione with a minimal effect. The effect of replacing the heptanedione with beta-keto esters and monoketones was also investigated. Maintaining the hexamethylene bridge and heptanedione, the methylenedioxy group was replaced with various substitutents. In general, most substituents did not adversely affect activity particularly against equine rhinovirus although there was some variation in activity against herpesvirus. Strongly hydrophilic groups significantly reduced activity. Finally, the effect of varying the length of the alkyl bridge was examined in the 4-hydroxyphenyl series, where peak activity was attained with n = 8.