甲基2-(二氟甲基)-5-(4,5-二氢-1,3-噻唑-2-基)-4-(2-甲基丙基)-6-(三氟甲基)吡啶-3-羧酸酯 | 147034-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 甲基2-(二氟甲基)-5-(4,5-二氢-1,3-噻唑-2-基)-4-(2-甲基丙基)-6-(三氟甲基)吡啶-3-羧酸酯
• 英文名称: 5,7-Dimethylnaphthalen-1-amine
• CAS: 147034-11-5
• 化学式: C₁₂H₁₃N
• mdl: MFCD18810634
• 分子量: 171.242
• InChiKey: NDDYXDGQJRAXHP-UHFFFAOYSA-N

物化性质

• 沸点：
  332.9±11.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲基2-(二氟甲基)-5-(4,5-二氢-1,3-噻唑-2-基)-4-(2-甲基丙基)-6-(三氟甲基)吡啶-3-羧酸酯 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Pd-Catalyzed Semmler–Wolff Reactions for the Conversion of Substituted Cyclohexenone Oximes to Primary Anilines

  摘要：

  Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd-0(PCy3)(2), and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.

  DOI：

  10.1021/ja4073172
• 作为产物：
  描述：

  5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one O-pivaloyl oxime 在 palladium diacetate 、 potassium carbonate 、 三环戊基膦 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以80%的产率得到甲基2-(二氟甲基)-5-(4,5-二氢-1,3-噻唑-2-基)-4-(2-甲基丙基)-6-(三氟甲基)吡啶-3-羧酸酯
  参考文献：
  名称：

  Pd-Catalyzed Semmler–Wolff Reactions for the Conversion of Substituted Cyclohexenone Oximes to Primary Anilines

  摘要：

  Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd-0(PCy3)(2), and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.

  DOI：

  10.1021/ja4073172

文献信息

• Janin Yves L., Bisagni Emile, Synthesis (BRD), (1993) N 1, S 57-59
  作者：Janin Yves L., Bisagni Emile

  DOI：——

  日期：——
• Pd-Catalyzed Semmler–Wolff Reactions for the Conversion of Substituted Cyclohexenone Oximes to Primary Anilines
  作者：Wan Pyo Hong、Andrei V. Iosub、Shannon S. Stahl

  DOI：10.1021/ja4073172

  日期：2013.9.18

  Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd-0(PCy3)(2), and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.