1-(6-苯基萘-2-基)乙酮 | 1048964-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(6-苯基萘-2-基)乙酮
• 英文名称: 1-(6-phenylnaphthalen-2-yl)ethanone
• 英文别名: 2-acetyl-6-phenylnaphthalene
• CAS: 1048964-07-3
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: IVZBWYDRGBXSBI-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143 °C
• 沸点：
  415.1±14.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(6-苯基萘-2-基)乙酮 在 sodium perborate tetrahydrate 、 溶剂黄146 、 三氟乙酸 作用下， 以60%的产率得到
  参考文献：
  名称：

  Biaryl Construction via Ni-Catalyzed C−O Activation of Phenolic Carboxylates

  摘要：

  Biaryl scaffolds were constructed via Ni-catalyzed aryl C-O activation by avoiding cleavage of the more reactive acyl C-O bond aryl carboxylates. Now aryl esters, in general, can be successfully employed in cross-coupling reactions for the first time. The substrate scope and synthetic utility of the chemistry were demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. Water was observed to play an important role in facilitating this transformation.

  DOI：

  10.1021/ja8056503
• 作为产物：
  描述：

  苯硼酸酐 、 6-acetyl-2-naphthyl acetate 在 potassium phosphate 、 二氯化双(三环己基膦)镍(II) 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以76%的产率得到1-(6-苯基萘-2-基)乙酮
  参考文献：
  名称：

  Biaryl Construction via Ni-Catalyzed C−O Activation of Phenolic Carboxylates

  摘要：

  Biaryl scaffolds were constructed via Ni-catalyzed aryl C-O activation by avoiding cleavage of the more reactive acyl C-O bond aryl carboxylates. Now aryl esters, in general, can be successfully employed in cross-coupling reactions for the first time. The substrate scope and synthetic utility of the chemistry were demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. Water was observed to play an important role in facilitating this transformation.

  DOI：

  10.1021/ja8056503

文献信息

• Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids
  作者：Hu Chen、Zhongbin Huang、Xiaoming Hu、Guo Tang、Pengxiang Xu、Yufen Zhao、Chien-Hong Cheng

  DOI：10.1021/jo2000034

  日期：2011.4.1

  The Suzuki−Miyaura cross-coupling of aryl phosphates using Ni(PCy3)2Cl2 as an inexpensive, bench-stable catalyst is described. Broad substrate scope and high efficiency are demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. The poor reactivity of aryl phosphates relative to aryl halides is successfully employed to construct polyarenes by selective cross-coupling

  描述了使用Ni（PCy 3）2 Cl 2作为廉价，稳定的催化剂对芳基磷酸酯进行的Suzuki-Miyaura交叉偶联。超过40个联芳基的合成以及构建复杂的有机分子证明了广泛的底物范围和高效率。通过使用Pd和Ni催化剂进行选择性交叉偶联，成功地将磷酸芳基酯相对于芳基卤化物的不良反应性用于构建聚芳烃。
• Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers with Aryl Boronic Esters
  作者：Mamoru Tobisu、Toshiaki Shimasaki、Naoto Chatani

  DOI：10.1002/anie.200801447

  日期：2008.6.16