3-(3-phenoxyphenyl)propanenitrile | 1057676-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-phenoxyphenyl)propanenitrile
• CAS: 1057676-70-6
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: UMVAPPCMBNDGKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  3-(3-phenoxyphenyl)propanenitrile 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 3-(3-苯氧基苯基)丙烷-1-胺
  参考文献：
  名称：

  Inhibition of Staphyloxanthin Virulence Factor Biosynthesis in Staphylococcus aureus: In Vitro, in Vivo, and Crystallographic Results

  摘要：

  The gold color of Staphylococcus aureus is derived from the carotenoid staphyloxanthin, a virulence factor for the organism. Here, we report the synthesis and activity of a broad variety of staphyloxanthin biosynthesis inhibitors that inhibit the first committed step in its biosynthesis, condensation of two farnesyl diphosphate (FPP) molecules to dehydrosqualene, catalyzed by the enzyme dehydrosqualene synthase (CrtM). The most active compounds are phosphonoacetamides that have low nanomolar K-i values for CrtM inhibition and are active in whole bacterial cells and in mice, where they inhibit S. aureus disease progression. We also report the X-ray crystallographic structure of the most active compound, N-3-(3-phenoxyphenyl)propylphosphonoacetamide (IC50 = 8 nM, in cells), bound to CrtM. The structure exhibits a complex network of hydrogen bonds between the polar headgroup and the protein, while the 3-phenoxyphenyl side chain is located in a hydrophobic pocket previously reported to bind farnesyl thiodiphosphate (FsPP), as well as biphenyl phosphonosulfonate inhibitors. Given the good enzymatic, whole cell, and in vivo pharmacologic activities, these results should help guide the further development of novel antivirulence factor-based therapies for S. aureus infections.

  DOI：

  10.1021/jm9001764
• 作为产物：
  描述：

  间苯氧基苯甲醛 在 5%-palladium/activated carbon 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 3-(3-phenoxyphenyl)propanenitrile
  参考文献：
  名称：

  高效稳定的Vγ9Vδ2 T细胞的小分子激动剂

  摘要：

  本发明涉及式(I)化合物作为高效稳定的Vγ9Vδ2 T细胞的小分子激动剂，其中各基团定义如说明书和权利要求书所详述。本发明还涉及含有式(I)化合物的药物组合物以及它们在治疗增殖性疾病中的用途。

  公开号：

  CN109651429A

文献信息

• β‐Aryl Nitrile Construction<i>via</i>Palladium‐Catalyzed Decarboxylative Benzylation of α‐Cyano Aliphatic Carboxylate Salts
  作者：Rui Shang、Zheng Huang、Xiao Xiao、Xi Lu、Yao Fu、Lei Liu

  DOI：10.1002/adsc.201200383

  日期：2012.9.17

  The palladium‐catalyzed decarboxylative benzylation of α‐cyano aliphatic carboxylate salts with benzyl electrophiles was discovered. This reaction exhibits good functional group compatibility and proceeds under relatively mild conditions. A diverse range of quaternary, tertiary and secondary β‐aryl nitriles can be conveniently prepared by this method.

  发现了α-氰基脂肪族羧酸盐与苄基亲电试剂的钯催化脱羧苄基化反应。该反应表现出良好的官能团相容性，并且在相对温和的条件下进行。通过这种方法可以方便地制备各种范围的季，叔和仲β-芳基腈。
• Formal reductive addition of acetonitrile to aldehydes and ketones
  作者：Karim Muratov、Ekaterina Kuchuk、Sreekumar Vellalath、Oleg I. Afanasyev、Alexei P. Moskovets、Gleb Denisov、Denis Chusov

  DOI：10.1039/c8ob01992d

  日期：——

  An efficient and highly productive rhodium-catalyzed method for the synthesis of nitriles employing aldehydes or ketones, methyl cyanoacetate, water and carbon monoxide as starting materials has been developed. Simple rhodium chloride without any ligands can be used. The fine tuning of the substrate can lead to the activity higher than 5000 TON.

  已经开发出一种高效且高产的铑催化的方法，该方法使用醛或酮，氰基乙酸甲酯，水和一氧化碳作为起始原料来合成腈。可以使用没有任何配体的简单氯化铑。基板的微调可导致活性高于5000吨。
• ANTI-BACTERIAL COMPOSITIONS AND METHODS INCLUDING TARGETING VIRULENCE FACTORS OF STAPHYLOCOCCUS AUREUS
  申请人：Oldfield Eric

  公开号：US20120022024A1

  公开（公告）日：2012-01-26

  This disclosure relates to compositions and methods including for the inhibition, prevention, and/or treatment of microbial infections, including infections from such pathogens as Staphylococcus aureus.

  本公开涉及包括用于抑制、预防和/或治疗微生物感染的组合物和方法，包括对金黄色葡萄球菌等病原体引起的感染。
• Synthesis of nitriles containing 3-phenoxyphenyl fragment
  作者：Yu. V. Popov、T. G. Korchagina、V. S. Kamaletdinova

  DOI：10.1134/s107036321004016x

  日期：2010.4

  Reactions of the aldol-crotonic condensation, acylation of acetonitrile, and addition of amine to the activated double bond of acrylonitrile in the series of diphenyl oxide derivatives are studied. Effective procedures for preparing the nitriles containing diphenyl oxide fragment like 3-(3-phenoxyphenyl)-propenonitrile, 3-(3-phenoxyphenyl)-2-butenonitrile, 3-phenoxybenzoylacetonitrile, 3-(3-phenoxyphenyl)-propionitrile, and 3-phenoxybenzylamino)propionitrile are developed.
• Synthesis of 2-(3-phenoxyphenyl)-substituted benzoxazoles, based on nitriles containing the diphenyl oxide fragment
  作者：Yu. V. Popov、T. K. Korchagina、V. S. Lobasenko

  DOI：10.1007/s10593-011-0822-0

  日期：2011.9