2-(4-Methoxyphenyl)-vinyl-cyclopropyl-keton | 72881-75-5

• 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-Methoxyphenyl)-vinyl-cyclopropyl-keton
• 英文别名: 1-Cyclopropyl-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 72881-75-5
• 化学式: C₁₃H₁₄O₂
• mdl: MFCD00019236
• 分子量: 202.253
• InChiKey: OETDGAVCXAJYJG-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C(Solv: hexane (110-54-3))
• 沸点：
  361.7±17.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• 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：

  2-(4-Methoxyphenyl)-vinyl-cyclopropyl-keton 在 lithium aluminium tetrahydride 作用下， 生成 2-(4-Methoxyphenyl)ethyl cyclopropyl carbinol
  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：

  环丙甲基酮 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(4-Methoxyphenyl)-vinyl-cyclopropyl-keton
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrazoline derivatives as anti-inflammatory and antioxidant agents

  摘要：

  通过查耳酮 1a-h 与硫代氨基脲或盐酸氨基脲的环化反应，合成了一系列新型 5-芳基-3-环丙基-4,5-二氢吡唑衍生物 2a-p，并将其作为抗炎/抗氧化剂进行了评估。元素分析和光谱数据证实了这些化合物的结构。还测定了它们对超氧化物的自由基清除活性。还测定了它们对肝细胞活力和 LPS 刺激巨噬细胞产生一氧化氮（NO）的影响。结果表明，化合物 2e 和 2n 具有最高的自由基清除活性和抗炎活性，因此可用于预防氧化应激和炎症相关疾病。

  DOI：

  10.1007/s12272-012-0606-9

文献信息

• Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes and CO for the synthesis of α, β-cyclohexenones
  作者：Cheng-Hang Liu、Zhe Zhuang、Sritama Bose、Zhi-Xiang Yu

  DOI：10.1016/j.tet.2016.01.046

  日期：2016.6

  A Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes (VCPs) and CO to α, β-cyclohexenones has been developed. The reaction can tolerate aryl and aliphatic groups at the α-position of VCPs, while VCP substrates with vinyl or alkynyl substitutions are not suitable ones. In addition, this reaction can also be used to synthesize bicyclic rings if an aryl group is attached to the vinyl moiety of

  已经开发出Fe 2（CO）9介导的乙烯基环丙烷（VCP）和CO与α，β-环己烯酮的[5 + 1]环加成反应。该反应可以耐受VCPsα位的芳基和脂族基团，而带有乙烯基或炔基取代基的VCP底物不是合适的。另外，如果芳基连接至底物的乙烯基部分，则该反应也可用于合成双环。与Fe（CO）5介导的[5 + 1]反应相比，便宜，安全的Fe 2（CO）9的使用和放弃光辐照条件是本方法的两个主要优点。
• COMPOUNDS AND COMPOSITIONS FOR NEMATODE TREATMENT
  申请人：IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.

  公开号：US20210298295A1

  公开（公告）日：2021-09-30

  Disclosed herein are compounds and compositions for nematode treatment. In particular, disclosed are compounds of formula (I), a method of treating a plant or a growing media for a nematode with compounds of formula (II), compositions, and methods of use.

  本文披露了用于线虫治疗的化合物和组合物。具体而言，披露了公式（I）的化合物，以及使用公式（II）的化合物治疗植物或生长介质中的线虫的方法、组合物和使用方法。
• 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.
• Synthesis and biological evaluation of novel pyrazoline derivatives as anti-inflammatory and antioxidant agents
  作者：Nadia A. Khalil、Eman M. Ahmed、Hala B. El-Nassan、Osama K. Ahmed、Ahmed M. Al-Abd

  DOI：10.1007/s12272-012-0606-9

  日期：2012.6

  A series of novel 5-aryl-3-cyclopropyl-4,5-dihydropyrazole derivatives 2a–p were synthesized via cyclization of chalcones 1a–h with thiosemicarbazide or semicarbazide HCl and evaluated as anti-inflammatory/antioxidant agents. The structures were confirmed by elemental analyses and spectral data. The free radical scavenging activity toward superoxide was determined. Their effect on hepatocytes viability and nitric oxide (NO) production in LPS-stimulated macrophages was also determined. The results showed that compounds 2e and 2n demonstrated the highest free-radical scavenging and anti-inflammatory activities, thus can be useful in the prevention of oxidative stress and inflammation-related disorders.

  通过查耳酮 1a-h 与硫代氨基脲或盐酸氨基脲的环化反应，合成了一系列新型 5-芳基-3-环丙基-4,5-二氢吡唑衍生物 2a-p，并将其作为抗炎/抗氧化剂进行了评估。元素分析和光谱数据证实了这些化合物的结构。还测定了它们对超氧化物的自由基清除活性。还测定了它们对肝细胞活力和 LPS 刺激巨噬细胞产生一氧化氮（NO）的影响。结果表明，化合物 2e 和 2n 具有最高的自由基清除活性和抗炎活性，因此可用于预防氧化应激和炎症相关疾病。