(E)-2-ethoxymethylene-butyramide | 173987-37-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-ethoxymethylene-butyramide
• 英文别名: (2E)-2-(ethoxymethylidene)butanamide
• CAS: 173987-37-6
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: FVQCAEROOYHRCW-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-ethoxymethylene-butyramide 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 35.34h， 生成 (+)-1-<(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione
  参考文献：
  名称：

  A Short High Yielding Synthesis of the Potent Anti-VZV Carbocyclic Nucleoside Analogue Carba-BVDU

  摘要：

  A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2'-deoxy-4'a-carbauridine 5. In situ acetylation of 5 afforded 3',5'-di-O-acetyl-5-ethyl-2'-deoxy-4'a-carbauridine 6 in 78% overall yield from 2. Radical bromination of 6 with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3',5'-di-O-acetyl-5-(E)-(2-bromovinyl)-2'-deoxy-4'a-carbauridine 7. Deacetylation of 7 afforded 1 in an overall 45-53% yield from 2.

  DOI：

  10.1080/15257779508010722
• 作为产物：
  描述：

  (3E)-1,1,1-trichloro-3-(ethoxymethylidene)pentan-2-one 在 氢氧化钾 、 ammonium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 水 、 甲苯 为溶剂， 反应 4.0h， 生成 (E)-2-ethoxymethylene-butyramide
  参考文献：
  名称：

  A Short High Yielding Synthesis of the Potent Anti-VZV Carbocyclic Nucleoside Analogue Carba-BVDU

  摘要：

  A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2'-deoxy-4'a-carbauridine 5. In situ acetylation of 5 afforded 3',5'-di-O-acetyl-5-ethyl-2'-deoxy-4'a-carbauridine 6 in 78% overall yield from 2. Radical bromination of 6 with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3',5'-di-O-acetyl-5-(E)-(2-bromovinyl)-2'-deoxy-4'a-carbauridine 7. Deacetylation of 7 afforded 1 in an overall 45-53% yield from 2.

  DOI：

  10.1080/15257779508010722