cyclopropyl(2-(methylamino)phenyl)methanone | 1610460-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclopropyl(2-(methylamino)phenyl)methanone
• 英文别名: Cyclopropyl-[2-(methylamino)phenyl]methanone
• CAS: 1610460-98-4
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: AWWLEMSWOUNSQW-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclopropyl(2-(methylamino)phenyl)methanone 在 silica gel 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 3-benzyl-3-cyclopropyl-1-methylindolin-2-one
  参考文献：
  名称：

  硅胶介导的2-烷基氨基苯基prop-1-yn-3-ols的水胺化/ Semipinacol重排：由炔烃和1-（2-氨基苯基）酮合成2-Oxindoles

  摘要：

  Abstract2‐Alkylaminophenylprop‐1‐yn‐3‐ols, prepared from the lithium diisopropylamide (LDA)‐mediated 1,2‐addition of alkynes to 1‐(2‐aminophenyl) ketones, can be converted to 3,3‐disubstituted 2‐oxindoles by using silica gel in n‐hexane/ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale‐up strategy for the synthesis of 2‐oxindoles was exemplified by the large‐scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.magnified image

  DOI：

  10.1002/adsc.201300911
• 作为产物：
  描述：

  (2-氨基苯基)环丙基甲酮 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以41%的产率得到cyclopropyl(2-(methylamino)phenyl)methanone
  参考文献：
  名称：

  硅胶介导的2-烷基氨基苯基prop-1-yn-3-ols的水胺化/ Semipinacol重排：由炔烃和1-（2-氨基苯基）酮合成2-Oxindoles

  摘要：

  Abstract2‐Alkylaminophenylprop‐1‐yn‐3‐ols, prepared from the lithium diisopropylamide (LDA)‐mediated 1,2‐addition of alkynes to 1‐(2‐aminophenyl) ketones, can be converted to 3,3‐disubstituted 2‐oxindoles by using silica gel in n‐hexane/ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale‐up strategy for the synthesis of 2‐oxindoles was exemplified by the large‐scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.magnified image

  DOI：

  10.1002/adsc.201300911

文献信息

• Silica Gel-Mediated Hydroamination/Semipinacol Rearrangement of 2-Alkylaminophenylprop-1-yn-3-ols: Synthesis of 2-Oxindoles from Alkynes and 1-(2-Aminophenyl) Ketones
  作者：Dewi Susanti、Linda Li Ru Ng、Philip Wai Hong Chan

  DOI：10.1002/adsc.201300911

  日期：2014.2.10

  Abstract2‐Alkylaminophenylprop‐1‐yn‐3‐ols, prepared from the lithium diisopropylamide (LDA)‐mediated 1,2‐addition of alkynes to 1‐(2‐aminophenyl) ketones, can be converted to 3,3‐disubstituted 2‐oxindoles by using silica gel in n‐hexane/ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale‐up strategy for the synthesis of 2‐oxindoles was exemplified by the large‐scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.magnified image