4-azido-1-(3-methoxyphenyl)butan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-azido-1-(3-methoxyphenyl)butan-1-one
• 英文别名: 4-Azido-1-(3-methoxyphenyl)butan-1-one
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: HICATLFBJHXMRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-azido-1-(3-methoxyphenyl)butan-1-one 在 水 、 三苯基膦 、 lithium hexamethyldisilazane 、 肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Pyrazole-based sulfonamide and sulfamides as potent inhibitors of mammalian 15-lipoxygenase

  摘要：

  A series of inhibitors of mammalian 15-lipoxygenase (15-LO) based on a 3,4,5-tri-substituted pyrazole scaffold is described. Replacement of a sulfonamide functionality in the lead series with a sulfamide group resulted in improved physicochemical properties generating analogs with enhanced inhibition in cell-based and whole blood assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.107
• 作为产物：
  描述：

  1-(3-methoxyphenyl)cyclobutan-1-ol 在 2,2'-联吡啶 、 1-羟基-1,2-苯碘酰-3(1H)-酮 、 叠氮基三甲基硅烷 、 manganese(III) triacetate dihydrate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以80%的产率得到4-azido-1-(3-methoxyphenyl)butan-1-one
  参考文献：
  名称：

  锰催化环丁醇的氧化叠氮化：C ？的区域特异性合成烷基叠氮化物 C键解理

  摘要：

  描述了一种新型的锰催化的环丁醇的氧化叠氮化。产生了大量伯，仲和叔烷基叠氮化物，具有合成上有用的产率和唯一的区域选择性。除了线性烷基叠氮化物外，还容易制备难以捉摸的中型环状叠氮化物。初步机理研究表明，该反应可能是由自由基介导的C转入 C键裂解/ C  Ñ 3键的形成通路。

  DOI：

  10.1002/anie.201506578

文献信息

• Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by CC Bond Cleavage
  作者：Rongguo Ren、Huijun Zhao、Leitao Huan、Chen Zhu

  DOI：10.1002/anie.201506578

  日期：2015.10.19

  azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, otherwise elusive medium‐sized cyclic azides were also readily prepared. Preliminary mechanistic studies reveal that the reaction likely proceeds by a radical‐mediated CC bond cleavage/CN3 bond

  描述了一种新型的锰催化的环丁醇的氧化叠氮化。产生了大量伯，仲和叔烷基叠氮化物，具有合成上有用的产率和唯一的区域选择性。除了线性烷基叠氮化物外，还容易制备难以捉摸的中型环状叠氮化物。初步机理研究表明，该反应可能是由自由基介导的C转入 C键裂解/ C  Ñ 3键的形成通路。
• Discovery of selective imidazole-based inhibitors of mammalian 15-lipoxygenase: Highly potent against human enzyme within a cellular environment
  作者：David S. Weinstein、Wen Liu、Khehyong Ngu、Charles Langevine、Donald W. Combs、Shaobin Zhuang、Cindy Chen、Cort S. Madsen、Timothy W. Harper、Jeffrey A. Robl

  DOI：10.1016/j.bmcl.2007.07.011

  日期：2007.9

  A series of 2,4,5-tri-substituted imidazoles has proven to be highly potent in inhibiting mammalian 15-lipoxygenase (15LO) with excellent selectivity over human isozymes 5- and P-12-LO. Non-symmetrical sulfamides (e.g., 21a-n) were found to be suitable replacements for the earlier arylsulfonamide-containing members of this series (e.g., 2, 14a-p). Several members of these series also demonstrated potent inhibition of human 15-LO in a cell-based assay. (c) 2007 Elsevier Ltd. All rights reserved.
• Pyrazole-based sulfonamide and sulfamides as potent inhibitors of mammalian 15-lipoxygenase
  作者：Khehyong Ngu、David S. Weinstein、Wen Liu、Charles Langevine、Donald W. Combs、Shaobin Zhuang、Xing Chen、Cort S. Madsen、Timothy W. Harper、Saleem Ahmad、Jeffrey A. Robl

  DOI：10.1016/j.bmcl.2011.05.107

  日期：2011.7

  A series of inhibitors of mammalian 15-lipoxygenase (15-LO) based on a 3,4,5-tri-substituted pyrazole scaffold is described. Replacement of a sulfonamide functionality in the lead series with a sulfamide group resulted in improved physicochemical properties generating analogs with enhanced inhibition in cell-based and whole blood assays. (C) 2011 Elsevier Ltd. All rights reserved.
• Manganese‐Mediated Electrooxidative Ring‐Opening Azidation of Cyclobutanol Derivatives with TMSN3
  作者：Wenchao Gao、Jie Yang、Yong Teng、Wendian Li、Wenguang Li、Ting Li

  DOI：10.1002/adsc.202400101

  日期：——

  A Mn‐electrocatalytic ring‐opening azidation of tert‐cyclobutanols has been developed. The regioselective method is applicable for the azidation of a diverse array of cyclobutanols to provide γ‐azido ketones in 23‐91% yields under chemical oxidants‐free reaction conditions. Detailed mechanistic studies suggest the process of Mn‐mediated alkoxy radical generation followed by β‐scission to form carbon‐centered

  已开发出叔环丁醇的锰电催化开环叠氮化反应。该区域选择性方法适用于多种环丁醇的叠氮化，在无化学氧化剂的反应条件下以 23-91% 的产率提供 γ-叠氮酮。详细的机理研究表明，Mn介导的烷氧基自由基生成，随后β-断裂形成以碳为中心的自由基物质的过程可能参与了这种转变。