N-methoxy-N-methyl-2-bromo-2,3,3,3-tetrafluoropropanamide | 677353-90-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methoxy-N-methyl-2-bromo-2,3,3,3-tetrafluoropropanamide
• 英文别名: Propanamide, 2-bromo-2,3,3,3-tetrafluoro-N-methoxy-N-methyl-；2-bromo-2,3,3,3-tetrafluoro-N-methoxy-N-methylpropanamide
• CAS: 677353-90-1
• 化学式: C₅H₆BrF₄NO₂
• 分子量: 268.006
• InChiKey: JVYXJECXYBLGRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-2-bromo-2,3,3,3-tetrafluoropropanamide 在 苯甲醛 、 三苯基膦 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到2,3,3,3-tetrafluoro-N-methoxy-N-methyl-propionamide
  参考文献：
  名称：

  Highly Diastereoselective Reductive Coupling of 2-Bromo-2,3,3,3-tetrafluoropropanamide with Aldehydes Promoted by Triphenylphosphine−Titanium(IV) Isopropoxide. An Efficient Route to the Synthesis of erythro-α-Fluoro-α-(trifluoromethyl)-β-hydroxy Amides

  摘要：

  The reductive coupling reaction of N-methoxy-N-methyl-2-bromo-2,3,3,3-tetrafluoropropanamide (Weinreb amide) with various aldehydes under the influence of the combined reagent, 1.2 equiv each of triphenylphosphine and titanium(IV) isopropoxide, took place smoothly at ambient temperature to give the corresponding alpha-fluoro-alpha-(trifluoromethyl)-beta-hydroxy amides in a highly erythro-selective manner. The high erythro selectivity was also obtained even by employing a combination of triphenylphosphine (1.2 equiv) and a catalytic amount of titanium(IV) isopropoxide.

  DOI：

  10.1021/jo0358729
• 作为产物：
  描述：

  2-溴-2,3,3,3-四氟丙酰氯 、 二甲羟胺盐酸盐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-methoxy-N-methyl-2-bromo-2,3,3,3-tetrafluoropropanamide
  参考文献：
  名称：

  Highly Diastereoselective Reductive Coupling of 2-Bromo-2,3,3,3-tetrafluoropropanamide with Aldehydes Promoted by Triphenylphosphine−Titanium(IV) Isopropoxide. An Efficient Route to the Synthesis of erythro-α-Fluoro-α-(trifluoromethyl)-β-hydroxy Amides

  摘要：

  The reductive coupling reaction of N-methoxy-N-methyl-2-bromo-2,3,3,3-tetrafluoropropanamide (Weinreb amide) with various aldehydes under the influence of the combined reagent, 1.2 equiv each of triphenylphosphine and titanium(IV) isopropoxide, took place smoothly at ambient temperature to give the corresponding alpha-fluoro-alpha-(trifluoromethyl)-beta-hydroxy amides in a highly erythro-selective manner. The high erythro selectivity was also obtained even by employing a combination of triphenylphosphine (1.2 equiv) and a catalytic amount of titanium(IV) isopropoxide.

  DOI：

  10.1021/jo0358729

文献信息

• Highly Stereoselective Aldol-type Reaction of 2-Bromo-2,3,3,3-tetrafluoropropanamide with Aldehydes Leading to<i>erythro</i>-α-Fluoro-α-(trifluoromethyl)-β-hydroxy Amides
  作者：Kei Sato、Takashi Sekiguchi、Takashi Ishihara、Tsutomu Konno、Hiroki Yamanaka

  DOI：10.1246/cl.2004.154

  日期：2004.2

  N-Methoxy-N-methyl-2-bromo-2,3,3,3-tetrafluoropropanamide underwent highly stereoselective aldol-type reaction with various aldehydes under the influence of triphenylphosphine—a catalytic amount of titanium(IV) isopropoxide at room temperature to give the erythro-isomers of α-fluoro-α-(trifluoromethyl)-β-hydroxy amides preferentially in good to excellent yields.

  N-甲氧基-N-甲基-2-溴-2,3,3,3-四氟丙酰胺在室温下与三苯基膦（催化量的钛（IV）异丙醇）作用，与各种醛发生高度立体选择性醛缩反应，优先生成α-氟-α-（三氟甲基）-β-羟基酰胺的红异构体，收率良好至极佳。