m-cyanophenacyl azide | 83112-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: m-cyanophenacyl azide
• 英文别名: 3-(2-Azidoacetyl)benzonitrile
• CAS: 83112-77-0
• 化学式: C₉H₆N₄O
• 分子量: 186.173
• InChiKey: NFRPJRHXTKGAQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  m-cyanophenacyl azide 在 lithium aluminium tetrahydride 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 4.5h， 生成 5-[3-(aminomethyl)phenyl]-N-(4-fluorophenyl)oxazol-2-amine
  参考文献：
  名称：

  Structure-activity relationship (SAR) studies of N-(3-methylpyridin-2-yl)-4-(pyridin-2-yl)thiazol-2-amine (SRI-22819) as NF-ҡB activators for the treatment of ALS

  摘要：

  DOI：

  10.1016/j.ejmech.2020.112952
• 作为产物：
  描述：

  3-(2-溴乙酰基)苯甲腈 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 m-cyanophenacyl azide
  参考文献：
  名称：

  Structure-activity relationship (SAR) studies of N-(3-methylpyridin-2-yl)-4-(pyridin-2-yl)thiazol-2-amine (SRI-22819) as NF-ҡB activators for the treatment of ALS

  摘要：

  DOI：

  10.1016/j.ejmech.2020.112952

文献信息

• Iodine-Mediated Condensation-Cyclization of α-Azido Ketones with <i>p</i> -Toluenesulfonyl Hydrazide for Synthesis of 4-Aryl-<i>NH</i> -1,2,3-Triazoles
  作者：Ming-Tian Ren、Min Li、An-Jing Wang、Jie Gao、Xiang-Xiang Zhang、Wen-Ming Shu

  DOI：10.1002/ejoc.202000146

  日期：2020.4.23

  An iodine‐mediated cyclization reaction leads to a wide variety of 4‐aryl‐NH‐1,2,3‐triazoles from α‐azido acetophenones and p‐toluenesulfonyl hydrazide is described. The reaction likely follows a condensation with intramolecular N–N bond formation

  碘介导的环化反应可从α-叠氮基苯乙酮和对甲苯磺酰肼中衍生出多种4-芳基NH 1,2,3-三唑。反应可能会随着分子内N–N键形成的缩合而发生
• Copper/TEMPO-Promoted Denitrogenation/Oxidation Reaction for Synthesis of Primary α-Ketoamides Using α-Azido Ketones
  作者：An-Jing Wang、Chun-Yan She、Yu-Die Zhang、Li-Han Zhao、Wen-Ming Shu、Wei-Chu Yu

  DOI：10.1021/acs.joc.2c01814

  日期：2022.12.2

  denitrogenation/oxidation reaction for the preparation of primary α-ketoamides was developed using α-azido ketones as a substrate and TEMPO as an oxidant. α-Azido ketones were denitrogenated in situ to form an imino ketone intermediate, which underwent a radical addition process and radical migration to form α-ketoamides. It is worth noting that the imino ketone intermediate is the key to this reaction.

  以 α-叠氮基酮为底物，TEMPO 为氧化剂，开发了铜 (II) 促进的脱氮/氧化反应，用于制备初级 α-酮酰胺。α-叠氮基酮原位脱氮形成亚氨基酮中间体，其经过自由基加成过程和自由基迁移形成α-酮酰胺。值得注意的是，亚氨基酮中间体是该反应的关键。
• Discovery and Evaluation of 2-Anilino-5-aryloxazoles as a Novel Class of VEGFR2 Kinase Inhibitors
  作者：Philip A. Harris、Mui Cheung、Robert N. Hunter、Matthew L. Brown、James M. Veal、Robert T. Nolte、Liping Wang、Wendy Liu、Renae M. Crosby、Jennifer H. Johnson、Andrea H. Epperly、Rakesh Kumar、Deirdre K. Luttrell、Jeffrey A. Stafford

  DOI：10.1021/jm049538w

  日期：2005.3.1

  A series of derivatives of 2-anilino-5-phenyloxazole (5) has been identified as inhibitors of VEGFR2 kinase. Herein we describe the structure-activity relationship (SAR) of this novel template. Optimization of both aryl rings led to very potent inhibitors at both the enzymatic and cellular levels. Oxazole 39 had excellent solubility and good oral PK when dosed as the bis-mesylate salt and demonstrated moderate in vivo efficacy against HT29 human colon tumor xenografts. X-ray crystallography confirmed the proposed binding mode, and comparison of oxazoles 39 and 46 revealed interesting differences in orientation of 2-pyridyl and 3-pyridyl rings, respectively, attached at the meta position of the 5-phenyl ring.
• Heterocyclic compounds
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0052442B1

  公开（公告）日：1985-09-11
• US4423045A
  申请人：——

  公开号：US4423045A

  公开（公告）日：1983-12-27