methyl 4-(2-bromoacetamido)but-2-ynoate | 899434-27-6

• 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: methyl 4-(2-bromoacetamido)but-2-ynoate
• 英文别名: Methyl 4-[(2-bromoacetyl)amino]but-2-ynoate；methyl 4-[(2-bromoacetyl)amino]but-2-ynoate
• CAS: 899434-27-6
• 化学式: C₇H₈BrNO₃
• 分子量: 234.049
• InChiKey: JSOPLIMCUOXDMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-bromoacetamido)but-2-ynoate 在 四丁基碘化铵 4-二甲氨基吡啶 、 4 A molecular sieve 、 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 (S)-6-(3,4-Dimethoxy-phenyl)-3-oxo-1,3,4,6,7,8-hexahydro-pyrido[1,2-a]pyrazine-2,9-dicarboxylic acid 2-tert-butyl ester 9-methyl ester
  参考文献：
  名称：

  A sequential reaction process to assemble polysubstituted indolizidines, quinolizidines and quinolizidine analogues

  摘要：

  The omega-iodo-alpha,beta-alkynoates and their ketone, sulfone or phosphonate analogues react with delta-chloropropylamines in MeCN assisted with K2CO3 to undergo a sequential S(N)2/Michael addition/S(N)2/S(N)2 reaction process, giving polysubstituted indolizidines or quinolizidines in good to excellent yields. This sequential reaction process is also compatible with three other substituted alpha,beta-alkynoates, affording quinolizidine analogues in moderate to good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.068
• 作为产物：
  描述：

  2-Bromo-N-[4-(tert-butyl-dimethyl-silanyloxy)-but-2-ynyl]-acetamide 在 jones reagent 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 0.5h， 生成 methyl 4-(2-bromoacetamido)but-2-ynoate
  参考文献：
  名称：

  A sequential reaction process to assemble polysubstituted indolizidines, quinolizidines and quinolizidine analogues

  摘要：

  The omega-iodo-alpha,beta-alkynoates and their ketone, sulfone or phosphonate analogues react with delta-chloropropylamines in MeCN assisted with K2CO3 to undergo a sequential S(N)2/Michael addition/S(N)2/S(N)2 reaction process, giving polysubstituted indolizidines or quinolizidines in good to excellent yields. This sequential reaction process is also compatible with three other substituted alpha,beta-alkynoates, affording quinolizidine analogues in moderate to good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.068