2-furyl 4-pyridyl ketone | 103851-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-furyl 4-pyridyl ketone
• 英文别名: furan-2-yl(pyridin-4-yl)methanone
• CAS: 103851-91-8
• 化学式: C₁₀H₇NO₂
• 分子量: 173.171
• InChiKey: BNEGDADTMJHLFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-furyl 4-pyridyl ketone 在 ammonium hydroxide 作用下， 反应 5.0h， 以35%的产率得到3-hydroxy-2-(4-pyridyl)pyridine
  参考文献：
  名称：

  Synthesis of 2-heteroaryl-3-hydroxypyridines by ring expansion reactions of 2-acylfurans with ammonia

  摘要：

  描述了一种简单且多用途的合成2-杂芳基-3-羟基吡啶衍生物的方法，即在150°C下将2-酰基呋喃与氨进行一步反应。

  DOI：

  10.1039/b105228b
• 作为产物：
  描述：

  furan-2-yl(pyridin-4-yl)methanol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 以91%的产率得到2-furyl 4-pyridyl ketone
  参考文献：
  名称：

  IBX，一种出色的 2-呋喃基甲醇氧化试剂：一种制备呋喃基酮的新通用方法

  摘要：

  描述了用邻碘苯甲酸 (IBX) 氧化各种 2-呋喃基甲醇的极好方法。这种方法提供了一种简单而有效的途径来获得各种 2-呋喃酮，否则这些物质是不容易获得的。

  DOI：

  10.1080/00397910903069673

文献信息

• Asymmetric Transfer Hydrogenation of Densely Functionalized Diheteroaryl and Diaryl Ketones by a Ru-Catalyst of Minimal Stereogenicity
  作者：Dongxu He、Xingjun Xu、Yi Lu、Min-Jie Zhou、Xiangyou Xing

  DOI：10.1021/acs.orglett.0c03064

  日期：2020.11.6

  functionalized diheteroaryl and diaryl ketones was developed using Ru-catalysts of minimal stereogenicity. Various ketone substrates with structurally and electronically similar groups attached to the prochiral centers were reduced successfully in good to excellent enantioselectivities and yields. This protocol provides practical and efficient access to chiral diheteroarylmethanols and benzhydrols,

  使用具有最小立体感的Ru催化剂开发了高度官能化的二杂芳基和二芳基酮的高度对映选择性不对称转移氢化（ATH）。在结构上和电子上相似的基团连接在前手性中心上的各种酮底物都成功地还原成良好的至优异的对映选择性和产率。该方案可提供对手性二杂芳基甲醇和苯甲醇的实用而有效的途径，它们是药物和生物活性化合物的关键中间体。
• Bioisosteric prototype design of biaryl imidazolyl and triazolyl competitive histamine H2-receptor antagonists
  作者：Christopher A. Lipinski、John L. LaMattina、P. J. Oates

  DOI：10.1021/jm00161a005

  日期：1986.11

  The structural relationship of the competitive histamine H2-receptor antagonist 3-amino-5-(2-amino-4-pyridyl)-1,2,4-triazole (1) to the agonist histamine and to antagonists of the cimetidine type was explored by the design and synthesis of four series of bioisosterically designed prototypes. Biological data from these series was best interpreted as indicating a similarity between the imidazole moiety of histamine and cimetidine and the 2-amino-4-pyridyl moiety of 1. On the basis of this data, sequential replacement of 2-amino-4-pyridyl by 2-[(dimethylamino)methyl]-5-furyl and 2-guanidino-4-triazolyl moieties led to a structurally more potent series of biaryl histamine H2-receptor antagonists. The best of these, 2-methyl-4-(2-guanidino-4-thiazolyl)imidazole (29, CP-57,361-1) was 120 times more potent as a histamine H2-receptor antagonist than 1.
• Indolizine Derivatives as HIV-1 VIF-ElonginC Interaction Inhibitors
  作者：Wenlin Huang、Tao Zuo、Xiao Luo、Hongwei Jin、Zhenming Liu、Zhenjun Yang、Xianghui Yu、Liangren Zhang、Lihe Zhang

  DOI：10.1111/cbdd.12119

  日期：2013.6

  Compound 1 (VEC‐5) was identified as a potent small‐molecular HIV‐1 viron infectivity factor inhibitor that targets the viron infectivity factor–ElonginC interaction. A structure–activity relationship study was carried out to develop compounds with improved efficacy against HIV‐1 and 49 indolizine derivatives of three categories were designed and synthesized. We found that five compounds exhibited promising anti‐HIV‐1 activity, and the most active compound 2g had an IC50 value of 11.0 μm. These results provide new information to develop highly potent small‐molecule HIV‐1 viron infectivity factor inhibitors.
• LIPINSKI C. A.; LAMATTINA J. L.; OATES P. J., J. MED. CHEM., 29,(1986) N 11, 2154-2163
  作者：LIPINSKI C. A.、 LAMATTINA J. L.、 OATES P. J.

  DOI：——

  日期：——
• Synthesis of 2-heteroaryl-3-hydroxypyridines by ring expansion reactions of 2-acylfurans with ammonia
  作者：Richard W. J. Chubb、Martin R. Bryce、Brian Tarbit

  DOI：10.1039/b105228b

  日期：——

  A straightforward and versatile synthesis of 2-heteroaryl-3-hydroxypyridine derivatives is described by the one-step reaction of 2-acylfurans with ammonia at 150 °C.

  描述了一种简单且多用途的合成2-杂芳基-3-羟基吡啶衍生物的方法，即在150°C下将2-酰基呋喃与氨进行一步反应。