1-(1-(hydroxyimino)ethyl)-N-p-tolylcyclopropanecarboxamide | 1021876-09-4

• 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: 1-(1-(hydroxyimino)ethyl)-N-p-tolylcyclopropanecarboxamide
• 英文别名: 1-(N-hydroxy-C-methylcarbonimidoyl)-N-(4-methylphenyl)cyclopropane-1-carboxamide
• CAS: 1021876-09-4
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: MTPZEPZYRWIVAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-(hydroxyimino)ethyl)-N-p-tolylcyclopropanecarboxamide 在 对甲苯磺酰氯 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以93%的产率得到7-methyl-5-p-tolyl-5,6-diazaspiro[2.4]hept-6-en-4-one
  参考文献：
  名称：

  Divergent synthesis of fully substituted isoxazoles and spiro-fused pyrazolin-5-ones from cyclopropyl oximes

  摘要：

  Efficient and divergent synthesis of fully substituted isoxazoles and spiro-fused pyrazolin-5-ones is developed from cyclopropyl oximes based on selection of reaction conditions. Under Appel conditions (PPh3/CBr4), substituted isoxazoles were synthesized from cyclopropyl oximes via a ring-opening and intramolecular cyclization process, whereas by treatment of cyclopropyl oximes with p-toluenesulfonyl chloride in the presence of potassium hydroxide, spiro-fused pyrazolin-5-ones were obtained via tandem ketoxime tosylation and intramolecular cyclization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.136
• 作为产物：
  描述：

  1-acetyl-N-(4-methylphenyl)cyclopropanecarboxamide 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 生成 1-(1-(hydroxyimino)ethyl)-N-p-tolylcyclopropanecarboxamide
  参考文献：
  名称：

  三氟甲磺酸介导的α-氨基甲酰基α-氧肟基环丙烷与DMF的开环/再循环反应：合成5-氨基异恶唑的途径

  摘要：

  摘要 在三氟甲磺酸酐（Tf 2 O）存在下，在非常温和的条件下，由α-环丙基β-肟基酰胺开发了一种简便高效的全取代5-氨基异恶唑合成方法。该过程涉及顺序的开环和分子内环化反应。 在三氟甲磺酸酐（Tf 2 O）存在下，在非常温和的条件下，由α-环丙基β-肟基酰胺开发了一种简便高效的全取代5-氨基异恶唑合成方法。该过程涉及顺序的开环和分子内环化反应。

  DOI：

  10.1055/s-0035-1561437

文献信息

• DAST-promoted Beckmann rearrangement/intramolecular cyclization of acyclic ketoximes: access to 2-oxazolines, benzimidazoles and benzoxazoles
  作者：Huiqin Li、Jian Qin、Zonglian Yang、Xiaoxue Guan、Lin Zhang、Peiqiu Liao、Xingqi Li

  DOI：10.1039/c5cc02155c

  日期：——

  The first example of DAST-promoted Beckmann rearrangement/intramolecular cyclization of acyclic ketoximes is described, which affords 2-oxazolines, benzimidazoles and benzoxazoles.

  DAST促进的无环酮肟的贝克曼重排/分子内环化的第一个例子被描述，产生2-噁唑烷，苯并咪唑和苯并噁唑。
• Efficient and Divergent Synthesis of Fully Substituted 1<i>H</i>-Pyrazoles and Isoxazoles from Cyclopropyl Oximes
  作者：Kewei Wang、Dexuan Xiang、Jinying Liu、Wei Pan、Dewen Dong

  DOI：10.1021/ol800178x

  日期：2008.5.1

  Efficient and divergent one-pot synthesis of fully substituted 1H-pyrazoles and isoxazoles from cyclopropyl oximes based on reaction conditions selection is reported. Under Vilsmeier conditions (POCl3/DMF), substituted 1 H-pyrazoles were synthesized from 1-carbamoyl, 1-oximyl cyclopropanes via sequential ring-opening, chlorovinylation, and intramolecular aza-cyclization. In the presence of POCl3/CH2Cl2

  据报道，根据反应条件的选择，可以从环丙基肟中高效，多样地一锅合成全取代的1H-吡唑和异恶唑。在Vilsmeier条件（POCl3 / DMF）下，通过顺序开环，氯乙烯基化和分子内氮杂环化反应，由1-氨基甲酰基，1-肟基环丙烷合成取代的1 H-吡唑。在POCl3 / CH2Cl2存在下，通过开环和分子内亲核乙烯基取代（SNV）反应从环丙基肟中获得取代的异恶唑。
• Triflic Anhydride-Mediated Beckmann Rearrangement Reaction of β-Oximyl Amides: Access to 5-Iminooxazolines
  作者：MANGFEI YU、QIAN ZHANG、JIA WANG、PENG HUANG、PENGFEI YAN、RUI ZHANG、DEWEN DONG

  DOI：10.1007/s12039-016-1085-1

  日期：2016.6

  Facile and efficient synthesis of 5-iminooxazolines from α,α-disubstituted β-oximyl amides mediated by triflic anhydride (Tf2O) in the presence of 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) in dichloromethane at room temperature is developed, and a mechanism involving tandem Beckmann rearrangement and intramolecular cyclization reaction is proposed. Facile and efficient synthesis of 5-iminooxazolines

  在1,8-二氮杂双环（5.4.0）十一碳烯-7-烯（DBU）存在下，由三氟酸酐（Tf 2 O）介导的α，α-二取代的β-肟基酰胺的高效合成。研制了室温下的二氯甲烷，提出了串联贝克曼重排和分子内环化反应的机理。 描述了在非常温和的条件下，通过串联三氟甲磺酸酐介导的贝克曼重排和分子内环化反应，由α，α-二取代的β-肟基酰胺轻松有效地合成5-亚氨基恶唑啉的方法。
• PIFA-Mediated Oxidative Cyclization of 1-Carbamoyl-1-oximylcycloalkanes: Synthesis of Spiro-Fused Pyrazolin-5-one <i>N</i>-Oxides
  作者：Kewei Wang、Xiaolan Fu、Jinying Liu、Yongjiu Liang、Dewen Dong

  DOI：10.1021/ol802952e

  日期：2009.2.19

  A convenient and efficient synthesis of spiro-fused pyrazolin-5-one N-oxides starting from readily available 1-carbamoyl-1-oximylcycloalkanes is developed. This general protocol features a novel and facile way for access to the five-membered azaheterocycles by formation of a new N-N single bond. The key cyclization step utilizes the formation of an N-oxonitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its subsequent intramolecular trapping by the amide moiety under rather mild experimental conditions.