N-ethoxycarbonyl-(E)-2-ethoxymethylene-butyramide | 173987-34-3

• 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: N-ethoxycarbonyl-(E)-2-ethoxymethylene-butyramide
• 英文别名: ethyl N-[(2E)-2-(ethoxymethylidene)butanoyl]carbamate
• CAS: 173987-34-3
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: RWTIWTCJYIFKCH-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-ethoxycarbonyl-(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 作用下， 以 1,4-二氧六环 为溶剂， 反应 34.34h， 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 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 N-ethoxycarbonyl-(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

文献信息

• Synthesis and biological properties of a new series of 5-substituted-pyrimidine-L-nucleoside analogues
  作者：Nigel B. Westwood、Richard T. Walker

  DOI：10.1016/s0040-4020(98)00821-7

  日期：1998.10

  trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L-nucleoside analogues incorporating non-standard 5-substituted-pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl)uracil-pyrrolidine-L-nucleosides 23-26. Of the compounds assessed for potential antiviral activity only 5-ethyluracil-(benzoyloxymethyl)pyrrolidine 20 was found to be a specific inhibitor of vaccinia virus. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A Short High Yielding Synthesis of the Potent Anti-VZV Carbocyclic Nucleoside Analogue Carba-BVDU
  作者：P. G. Wyatt、A. S. Anslow、B. A. Coomber、R. P.C. Cousins、D. N. Evans、V. S. Gilbert、D. C. Humber、I. L. Paternoster、S. L. Sollis、D. J. Tapolczay、G. G. Weingarten

  DOI：10.1080/15257779508010722

  日期：1995.11

  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.