2-hexoxybenzonitrile | 121554-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-hexoxybenzonitrile
• 英文别名: 2-(hexyloxy)benzonitrile
• CAS: 121554-15-2
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: BEIVVUUHIAJYFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hexoxybenzonitrile 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成 C₁₃H₂₀N₂O₂
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Monocyclic Pyrimidinones as Novel Inhibitors of PDE5

  摘要：

  Cyclic nucleotide phosphodiesterase type 5 (PDES) is a prime drug target for treating the diseases associated with a lower level of the cyclic guanosine monophosphate (cGMP), which is a specific substrate for PDE5 hydrolysis. Here we report a series of novel PDE5 inhibitors with the new scaffold of the monocyclic pyrimidin-4(3H)-one ring developed using the structure-based discovery strategy. In total, 37 derivatives of the pyrimidin-4(3H)-ones, were designed, synthesized, and evaluated for their inhibitory activities to PDES, resulting in 25 compounds with IC50 ranging from 1 to 100 nM and 11 compounds with IC50 ranging from 1 to 10 nM. Compound 5, 5,6-diethyl-2[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, the most potent compound, has an excellent IC50 (1.6 nM) in vitro and a good efficacy in a rat model of erection. It thus provides a potential candidate for the further development into a new drug targeting PDE5.

  DOI：

  10.1021/jm301159y
• 作为产物：
  描述：

  邻羟基苯甲腈 、 溴己烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以48%的产率得到2-hexoxybenzonitrile
  参考文献：
  名称：

  Rhodium-Catalyzed Alkenylation of Nitriles via Silicon-Assisted C−CN Bond Cleavage

  摘要：

  Rhodium-catalyzed Mizoroki-Heck type reaction of nitriles via the cleavage of C-C bonds is described. Orthogonal and iterative functionalizations of arenes were also demonstrated by combining the present and conventional halide-based cross-coupling reactions.

  DOI：

  10.1021/ol100481h

文献信息

• Semiheterogeneous Dual Nickel/Photocatalytic (Thio)etherification Using Carbon Nitrides
  作者：Cristian Cavedon、Amiera Madani、Peter H. Seeberger、Bartholomäus Pieber

  DOI：10.1021/acs.orglett.9b01957

  日期：2019.7.5

  nitride material can be combined with homogeneous nickel catalysts for light-mediated cross-couplings of aryl bromides with alcohols under mild conditions. The metal-free heterogeneous semiconductor is fully recyclable and couples a broad range of electron-poor aryl bromides with primary and secondary alcohols as well as water. The application for intramolecular reactions and the synthesis of active pharmaceutical

  可以将氮化碳材料与均相镍催化剂结合使用，以在温和条件下将芳基溴化物与醇进行光介导的交叉偶联。不含金属的异质半导体是完全可回收的，可将多种电子贫乏的芳族溴化物与伯醇和仲醇以及水偶合。证明了分子内反应和活性药物成分合成的应用。催化方案也适用于芳基碘化物与硫醇的偶联。
• Hird, Michael; Gray, George W.; Toyne, Kenneth J., Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 206, p. 205 - 221
  作者：Hird, Michael、Gray, George W.、Toyne, Kenneth J.

  DOI：——

  日期：——
• US8871777B2
  申请人：——

  公开号：US8871777B2

  公开（公告）日：2014-10-28
• Design, Synthesis, and Pharmacological Evaluation of Monocyclic Pyrimidinones as Novel Inhibitors of PDE5
  作者：Guan Wang、Zheng Liu、Tiantian Chen、Zhen Wang、Huaiyu Yang、Mingyue Zheng、Jing Ren、Guanghui Tian、Xiaojun Yang、Li Li、Jianfeng Li、Jin Suo、Rongxia Zhang、Xiangrui Jiang、Nicholas Kenneth Terrett、Jingshan Shen、Yechun Xu、Hualiang Jiang

  DOI：10.1021/jm301159y

  日期：2012.12.13

  Cyclic nucleotide phosphodiesterase type 5 (PDES) is a prime drug target for treating the diseases associated with a lower level of the cyclic guanosine monophosphate (cGMP), which is a specific substrate for PDE5 hydrolysis. Here we report a series of novel PDE5 inhibitors with the new scaffold of the monocyclic pyrimidin-4(3H)-one ring developed using the structure-based discovery strategy. In total, 37 derivatives of the pyrimidin-4(3H)-ones, were designed, synthesized, and evaluated for their inhibitory activities to PDES, resulting in 25 compounds with IC50 ranging from 1 to 100 nM and 11 compounds with IC50 ranging from 1 to 10 nM. Compound 5, 5,6-diethyl-2[2-n-propoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]pyrimid-4(3H)-one, the most potent compound, has an excellent IC50 (1.6 nM) in vitro and a good efficacy in a rat model of erection. It thus provides a potential candidate for the further development into a new drug targeting PDE5.
• Rhodium-Catalyzed Alkenylation of Nitriles via Silicon-Assisted C−CN Bond Cleavage
  作者：Yusuke Kita、Mamoru Tobisu、Naoto Chatani

  DOI：10.1021/ol100481h

  日期：2010.4.16

  Rhodium-catalyzed Mizoroki-Heck type reaction of nitriles via the cleavage of C-C bonds is described. Orthogonal and iterative functionalizations of arenes were also demonstrated by combining the present and conventional halide-based cross-coupling reactions.