ethyl N-phenoxyacetimidate | 1236291-45-4

• 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: ethyl N-phenoxyacetimidate
• 英文别名: ethyl O-phenylacetohydroxamate；ethyl N-phenoxyethanimidate
• CAS: 1236291-45-4
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: LYRSTOCARSVLOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl N-phenoxyacetimidate 在 盐酸 作用下， 以 水 为溶剂， 反应 2.5h， 以81.5%的产率得到O-苯基羟胺 盐酸盐
  参考文献：
  名称：

  O-取代羟胺盐酸盐及其制备方法

  摘要：

  本发明提供一种O‑取代羟胺盐酸盐及其制备方法，其中，制备方法包括如下步骤：步骤S1，向乙酰羟肟酸乙酯的乙醇溶液中加氢氧化钠，此外同时滴加卤代烃、磺酰氯或酰氯以发生取代反应，此后加到水中以析出O‑取代乙酰羟肟酸乙酯；步骤S2，将所述O‑取代乙酰羟肟酸乙酯加入盐酸溶液中回流反应以生成O‑取代羟胺盐酸盐。根据本发明实施例的O‑取代羟胺盐酸盐的制备方法，能够得到纯度高的产品，且该方法安全、易处理、工艺简单、适合工业化生产。

  公开号：

  CN108530315B
• 作为产物：
  描述：

  碘苯 在 三氟化硼乙醚 、 间氯过氧苯甲酸 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 ethyl N-phenoxyacetimidate
  参考文献：
  名称：

  Metal-Free One-Pot Synthesis of Benzofurans

  摘要：

  AbstractEthyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition‐metal‐free conditions. The obtained O‐arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]‐rearrangement, and cyclization in a fast and operationally simple one‐pot fashion without using excess reagents. Alternatively, the O‐arylated products could be isolated or transformed in situ to aryloxyamines or O‐arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)‐machaeriol B.

  DOI：

  10.1002/chem.201403523

文献信息

• Synthesis of α,β-Unsaturated <i>N</i>-Aryl Ketonitrones from Oximes and Diaryliodonium Salts: Observation of a Metal-Free <i>N</i>-Arylation Process
  作者：Xiao-Pan Ma、Wei-Min Shi、Xue-Ling Mo、Xiao-Hua Li、Liang-Gui Li、Cheng-Xue Pan、Bo Chen、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1021/acs.joc.5b01716

  日期：2015.10.16

  An efficient transition-metal-free method for the preparation of alpha,beta-unsaturated N-aryl ketonitrones under mild conditions has been developed. This reaction shows good functional group tolerance for both electron-rich and electron-deficient substituents on both oximes and diaryliodonium salts. Two examples of gram-scale preparations have been realized in good yields. Further transformations of these nitrones to different N-heterocycles have been demonstrated. DFT calculations suggest that N-arylation products are formed by [1,3]-phenyl migration of an O-coordinated oximate complex via a four-centered transition state, while the O-arylation products are formed by [1,3]-phenyl migration of a N-coordinated oximate complex.
• Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of <i>O</i>-Arylhydroxylamines and Substituted Benzofurans
  作者：Thomas J. Maimone、Stephen L. Buchwald

  DOI：10.1021/ja1044874

  日期：2010.7.28

  An efficient Pd catalyst for the O-arylation of ethyl acetohydroximate with aryl chlorides, bromides, and iodides has been developed. Ethyl acetohydroximate serves as an efficient hydroxylamine equivalent for C-O cross-coupling, thereby allowing for the preparation of O-arylhydroxylamines from simple aryl halides. Short reaction times and broad substrate scope, including heteroaryl coupling partners, allow access to O-arylhydroxylamines that would be difficult to prepare in a single step by traditional methods. Moreover, the O-arylated products so formed can be directly transformed into substituted benzofurans in a single operation.