1-(pyridin-4-yl)ethanone O-acetyl oxime | 3240-22-0

• 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: 1-(pyridin-4-yl)ethanone O-acetyl oxime
• 英文别名: 4-Acetyl-pyridin-O-acetyl-oxim；O-Acetyl-methyl-4-pyridyl-ketoxim；4-Acetyl-pyridin-O-acetyl-ketoxim；(1-Pyridin-4-ylethylideneamino) acetate
• CAS: 3240-22-0
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: PCLGAVYMUIMQDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(pyridin-4-yl)ethanone O-acetyl oxime 、 六氟乙酰丙酮 在 碘化铵 、 sodium dithionite 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以67%的产率得到4,6-bis(trifluoromethyl)-2,4'-bipyridine
  参考文献：
  名称：

  肟的无过渡金属的N–O还原：氟化吡啶的模块合成

  摘要：

  已开发出一种基于NH 4 I的还原系统，以促进肟N–O键的裂解，从而使多种药理学意义重大的氟化吡啶能够模块化合成。与传统的吡啶组装缩合方法相比，该方案具有高度的区域选择性和化学选择性，并具有广泛的官能团耐受性。

  DOI：

  10.1021/acs.orglett.7b01564
• 作为产物：
  描述：

  4-乙酰吡啶 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 1-(pyridin-4-yl)ethanone O-acetyl oxime
  参考文献：
  名称：

  通过Cu（i）介导的多米诺环化反应从乙酸肟和茚三酮获得吡咯并[2,1-a]异吲哚二酮。

  摘要：

  据报道，易于获得的肟肟与茚三酮的铜介导的多米诺缩合反应可通过新的CC和CN键形成吡咯并[2,1-a]异吲哚二酮。已显示出广泛的肟肟乙酸酯通常参与反应以优异的产率生产缩合产物。进行了必要的控制实验，并提出了涉及通过肟肟的Cu介导的NO键断裂顺序形成亚胺基自由基，将自由基添加到茚三酮中以及通过环扩展进行重排的机制。

  DOI：

  10.1039/d0ob00058b

文献信息

• Copper(0)/PPh₃-Mediated Bisheteroannulations of <i>o</i>-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls
  作者：Huanxin Meng、Zhenhua Xu、Zhonghua Qu、Huawen Huang、Guo-Jun Deng

  DOI：10.1021/acs.orglett.0c02180

  日期：2020.8.7

  A copper(0)/PPh3-mediated cascade bisheteroannulation reaction of o-nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C–I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh3-mediated deoxygenative

  已开发出铜 (0)/PPh 3介导的邻硝基炔烃与甲基酮肟的级联双杂环化反应，该反应为获得各种吡唑稠合假吲哚化合物提供了可行的途径。合成有用的官能团包括敏感的 C-I 键与该系统兼容。机理研究表明，反应级联涉及连续 PPh 3介导的脱氧环异构化和铜催化的 [3 + 2] 吡唑环化。
• Transition-Metal-Free N–O Reduction of Oximes: A Modular Synthesis of Fluorinated Pyridines
  作者：Huawen Huang、Jinhui Cai、Hao Xie、Jing Tan、Feifei Li、Guo-Jun Deng

  DOI：10.1021/acs.orglett.7b01564

  日期：2017.7.21

  An NH4I-based reductive system has been explored to promote the oxime N–O bond cleavage and thereby enable a modular synthesis of a broad range of pharmacologically significant fluorinated pyridines. Compared with traditional condensation methods for pyridine assembly, this protocol was found to be highly regio- and chemoselective and presented broad functional group tolerance.

  已开发出一种基于NH 4 I的还原系统，以促进肟N–O键的裂解，从而使多种药理学意义重大的氟化吡啶能够模块化合成。与传统的吡啶组装缩合方法相比，该方案具有高度的区域选择性和化学选择性，并具有广泛的官能团耐受性。
• Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines
  作者：Wei Wen Tan、Yew Jin Ong、Naohiko Yoshikai

  DOI：10.1002/anie.201704378

  日期：2017.7.3

  A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional

  据报道，乙酸肟肟和α，β-不饱和酮亚胺在铜催化下缩合反应生成吡啶衍生物。该反应具有温和的条件，相对于不对称肟肟酸酯的高官能团相容性和高的区域选择性，因此可以制备多种多取代的吡啶，其中许多不易通过常规缩合方法获得。
• Cu-Catalyzed Three-Component Cascade Annulation Reaction: An Entry to Functionalized Pyridines
  作者：Huanfeng Jiang、Jidan Yang、Xiaodong Tang、Jianxiao Li、Wanqing Wu

  DOI：10.1021/acs.joc.5b01621

  日期：2015.9.4

  A concise copper-catalyzed N-O bond cleavage/C-C/C-N bond formation procedure has been described for the synthesis of multisubstituted pyridines. Various oxime acetates, activated methylene compounds, and a wide range of aldehydes bearing aryl, heteroaryl, vinyl, and trifluoromethyl groups were employed to provide the tri- or tetrasubstituted pyridines with flexible substitution patterns. Moreover, this method features inexpensive catalysts, no need for extra oxidant, and high step-enconomy, which make it pratical and attractive.
• Copper-Catalyzed Intermolecular Cyclization between Oximes and Alkenes: A Facile Access to Spiropyrrolines
  作者：Bo Zhao、Hong-Wen Liang、Jie Yang、Zhen Yang、Ye Wei

  DOI：10.1021/acscatal.7b01876

  日期：2017.9.1

  A Cu-catalyzed protocol has been developed for the rapid construction of a wide spectrum of structurally interesting spiropyrroline skeletons. This method utilizes readily accessible ketoximes and alkenes as the starting materials and exhibits broad substrate scope and good functional group compatibility. Furthermore, the reaction can be applied for the late stage modification of bioactive pregnenolone derivatives. The mechanistic investigation suggests that the reactions proceed through a radical process.