1-([1,1′-biphenyl]-4-yl)-3-(1H-pyrazol-1-yl)propan-1-one | 108664-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-([1,1′-biphenyl]-4-yl)-3-(1H-pyrazol-1-yl)propan-1-one
• 英文别名: 1-(4-phenylphenyl)-3-pyrazol-1-ylpropan-1-one
• CAS: 108664-76-2
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: BUHUFNBTLQTFLV-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  469.5±28.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  四甲基甲烷二胺 、 1-([1,1′-biphenyl]-4-yl)-3-(1H-pyrazol-1-yl)propan-1-one 在 乙酸酐 作用下， 反应 1.5h， 以43%的产率得到1-(4-苯基苯基)-2-(吡唑-1-基甲基)丙-2-烯-1-酮
  参考文献：
  名称：

  Synthesis and antifungal activity of a series of novel 1,2-disubstituted propenones

  摘要：

  To find an antifungal agent other than those of the imidazole and triazole series, a new class of 1,2-disubstituted propenones I and II was prepared and tested for antifungal activity. Comparison of the structure-activity relationships showed that the conjugated structure of carbonyl and exomethylene groups in I and II plays an important role in potent antifungal activity. However, it is noteworthy that compounds 53, 54, and 56, which have a hydroxymethyl or methoxymethyl group instead of an exo-methylene group in I, also showed potent activity. Although many compounds exhibited strong antifungal activity in vitro, none showed activity in vivo of oral efficacy against subacute systemic candidiasis in mice.

  DOI：

  10.1021/jm00391a037
• 作为产物：
  描述：

  联苯单乙酮 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 31.0h， 生成 1-([1,1′-biphenyl]-4-yl)-3-(1H-pyrazol-1-yl)propan-1-one
  参考文献：
  名称：

  Synthesis and antifungal activity of a series of novel 1,2-disubstituted propenones

  摘要：

  To find an antifungal agent other than those of the imidazole and triazole series, a new class of 1,2-disubstituted propenones I and II was prepared and tested for antifungal activity. Comparison of the structure-activity relationships showed that the conjugated structure of carbonyl and exomethylene groups in I and II plays an important role in potent antifungal activity. However, it is noteworthy that compounds 53, 54, and 56, which have a hydroxymethyl or methoxymethyl group instead of an exo-methylene group in I, also showed potent activity. Although many compounds exhibited strong antifungal activity in vitro, none showed activity in vivo of oral efficacy against subacute systemic candidiasis in mice.

  DOI：

  10.1021/jm00391a037

文献信息

• Copper-Catalyzed <i>N</i>-Arylation of Azoles and Mannich-Type Coupling of Ketones and Azoles under Metal-Free Conditions
  作者：Kai Sun、Zhonghong Zhu、Jingjing Sun、Lulu Liu、Xin Wang

  DOI：10.1021/acs.joc.5b02593

  日期：2016.2.19

  five-membered heterocycles with azoles. Five-membered heterocycles bearing an acetyl group also underwent a Mannich-type reaction with activated azoles to give the corresponding β-amino ketones under metal-free conditions. These reactions exhibited wide substrate scope, high functional group tolerance, and ease of operation, making them useful tools with numerous potential applications in synthetic chemistry

  已经开发出一种新的方法，用于五元杂环与唑的铜催化直接N-芳基化。在无金属条件下，带有乙酰基的五元杂环也与活化的唑类发生曼尼希型反应，得到相应的β-氨基酮。这些反应具有广泛的底物范围，较高的官能团耐受性和易于操作的特性，使其成为有用的工具，在合成化学中具有众多潜在应用。
• OGATA, MASARU;MATSUMOTO, HIROSHI;KIDA, SHIRO;SHIMIZU, SUMIO;TAWARA, KATSU+, J. MED. CHEM., 30,(1987) N 8, 1497-1502
  作者：OGATA, MASARU、MATSUMOTO, HIROSHI、KIDA, SHIRO、SHIMIZU, SUMIO、TAWARA, KATSU+

  DOI：——

  日期：——