N-(1-ethoxycyclopropyl)-3,4-difluoro-2-methylaniline | 206546-14-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1-ethoxycyclopropyl)-3,4-difluoro-2-methylaniline
• CAS: 206546-14-7
• 化学式: C₁₂H₁₅F₂NO
• 分子量: 227.254
• InChiKey: RHJXGZUGBKXNNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-ethoxycyclopropyl)-3,4-difluoro-2-methylaniline 在 aluminum (III) chloride 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 以15.4 g的产率得到cyclopropyl(3,4-difluoro-2-methylphenyl)amine
  参考文献：
  名称：

  Air Oxidation of N-Cyclopropylanilines

  摘要：

  Air oxidation of N-cyclopropylanilines was shown to occur under either ambient conditions or accelerated conditions (warming or shining light) in an open container. A subsequent fragmentation resulted in formation of the corresponding acetamide. While potential mechanisms have been previously proposed, simple aerobic oxidation to beta-hydroxy-propionamides in the absence of a radical promoter has not been previously reported.

  DOI：

  10.1080/00397911.2010.545166
• 作为产物：
  描述：

  1-乙氧基-1-三甲硅氧基环丙烷 、 3,4-二氟-2-甲基苯胺 以 甲醇 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 N-(1-ethoxycyclopropyl)-3,4-difluoro-2-methylaniline
  参考文献：
  名称：

  Air Oxidation of N-Cyclopropylanilines

  摘要：

  Air oxidation of N-cyclopropylanilines was shown to occur under either ambient conditions or accelerated conditions (warming or shining light) in an open container. A subsequent fragmentation resulted in formation of the corresponding acetamide. While potential mechanisms have been previously proposed, simple aerobic oxidation to beta-hydroxy-propionamides in the absence of a radical promoter has not been previously reported.

  DOI：

  10.1080/00397911.2010.545166

文献信息

• PROCESS FOR PRODUCING N-CYCLOPROPYLANILINES AND INTERMEDIATES USED THEREFOR
  申请人：IHARA CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0990639A1

  公开（公告）日：2000-04-05

  The present invention aims at providing processes for production, from inexpensive raw materials of high commercial availability, of N-cyclopropylanilines which are an important intermediate in producing a quinolonecarboxylic acid having a cyclopropyl group at the 1-position, a fluorine atom at the 6-position and an alkyl group, an alkoxy group or a fluorine-substituted methoxy group at the 8-position (this quinolonecarboxylic acid is a useful synthetic antibacterial agent); and intermediates therefor. The present invention provides a process for producing an N-cyclopropyl-3,4-difluoroaniline represented by the general formula (4): which process comprises reacting, in the presence of an acid in an alcohol type solvent, a 3,4-difluoro-2-substituted-aniline represented by the general formula (1): with a 1-alkoxy-1-trialkylsilyloxycyclopropane represented by the general formula (2): to produce an N-alkoxycyclopropylaniline represented by the general formula (3): and then reducing the N-alkoxycyclopropylaniline.

  本发明的目的是提供利用商业供应量大的廉价原料生产N-环丙基苯胺的工艺，N-环丙基苯胺是生产喹啉羧酸的重要中间体，喹啉羧酸在1位上有一个环丙基，在6位上有一个氟原子，在8位上有一个烷基、一个烷氧基或一个氟取代的甲氧基（这种喹啉羧酸是一种有用的合成抗菌剂）；并提供其中间体。 本发明提供了一种由通式（4）代表的 N-环丙基-3,4-二氟苯胺的生产工艺： 该工艺包括在有酸存在的情况下，在醇类溶剂中使通式 (1) 所代表的 3,4-二氟-2-取代-苯胺与 1-烷氧基-1-三苯胺反应： 与通式（2）代表的 1-烷氧基-1-三烷基硅氧基环丙烷反应，生成 N-烷氧基环丙烷： 生成通式（3）代表的 N-烷氧基环丙基苯胺： 然后还原 N-烷氧基环丙基苯胺。
• US6162944A
  申请人：——

  公开号：US6162944A

  公开（公告）日：2000-12-19
• Air Oxidation of <i>N</i>-Cyclopropylanilines
  作者：Anthony Blackburn、Daniel M. Bowles、Timothy T. Curran、Hui Kim

  DOI：10.1080/00397911.2010.545166

  日期：2012.6.15

  Air oxidation of N-cyclopropylanilines was shown to occur under either ambient conditions or accelerated conditions (warming or shining light) in an open container. A subsequent fragmentation resulted in formation of the corresponding acetamide. While potential mechanisms have been previously proposed, simple aerobic oxidation to beta-hydroxy-propionamides in the absence of a radical promoter has not been previously reported.