2-Bromo-N-(2-cyano-ethyl)-N-phenyl-butyramide | 131792-99-9

• 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: 2-Bromo-N-(2-cyano-ethyl)-N-phenyl-butyramide
• 英文别名: 2-bromo-N-(2-cyanoethyl)-N-phenylbutanamide
• CAS: 131792-99-9
• 化学式: C₁₃H₁₅BrN₂O
• 分子量: 295.179
• InChiKey: UYTAKCQKXDBMQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-N-(2-cyano-ethyl)-N-phenyl-butyramide 在 磷酸 、 银 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-Benzyl-3-ethyl-piperidine-2,4-dione
  参考文献：
  名称：

  Asymmetric synthesis of the corynantheine alkaloids via an intramolecular Blaise reaction. (-)-Corynantheidol and (-)-dihydrocorynantheol

  摘要：

  An asymmetric total synthesis of the corynantheine family of alkaloids has been accomplished, leading to corynantheidol (1a) and dihydrocorynantheol (1b). Formal syntheses to corynantheidine and dihydrocorynantheine are also shown. The key to this asymmetric route is the use of (1) chiral beta-carboline formamidines, which allow high degrees of diastereoselection at C-3 with chloroacetonitrile, and (2) a new version of the Blaise reaction using Zn-Ag couple and ultrasonic radiation. These two synthetic techniques combine to allow an efficient entry into the title compounds. The overall yield of 1a was 16.4% in seven steps from starting carboline 5.

  DOI：

  10.1021/jo00006a024
• 作为产物：
  描述：

  2-溴丁酰溴 、 3-（苄氨基）丙腈 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以104 %的产率得到2-Bromo-N-(2-cyano-ethyl)-N-phenyl-butyramide
  参考文献：
  名称：

  Asymmetric synthesis of the corynantheine alkaloids via an intramolecular Blaise reaction. (-)-Corynantheidol and (-)-dihydrocorynantheol

  摘要：

  An asymmetric total synthesis of the corynantheine family of alkaloids has been accomplished, leading to corynantheidol (1a) and dihydrocorynantheol (1b). Formal syntheses to corynantheidine and dihydrocorynantheine are also shown. The key to this asymmetric route is the use of (1) chiral beta-carboline formamidines, which allow high degrees of diastereoselection at C-3 with chloroacetonitrile, and (2) a new version of the Blaise reaction using Zn-Ag couple and ultrasonic radiation. These two synthetic techniques combine to allow an efficient entry into the title compounds. The overall yield of 1a was 16.4% in seven steps from starting carboline 5.

  DOI：

  10.1021/jo00006a024

文献信息

• Asymmetric synthesis of the corynantheine alkaloids via an intramolecular Blaise reaction. (-)-Corynantheidol and (-)-dihydrocorynantheol
  作者：Richard L. Beard、A. I. Meyers

  DOI：10.1021/jo00006a024

  日期：1991.3

  An asymmetric total synthesis of the corynantheine family of alkaloids has been accomplished, leading to corynantheidol (1a) and dihydrocorynantheol (1b). Formal syntheses to corynantheidine and dihydrocorynantheine are also shown. The key to this asymmetric route is the use of (1) chiral beta-carboline formamidines, which allow high degrees of diastereoselection at C-3 with chloroacetonitrile, and (2) a new version of the Blaise reaction using Zn-Ag couple and ultrasonic radiation. These two synthetic techniques combine to allow an efficient entry into the title compounds. The overall yield of 1a was 16.4% in seven steps from starting carboline 5.