methyl 4-(N-benzyl-2-bromoacetamido)but-2-ynoate | 899434-28-7

• 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-(N-benzyl-2-bromoacetamido)but-2-ynoate
• 英文别名: Methyl 4-[benzyl-(2-bromoacetyl)amino]but-2-ynoate；methyl 4-[benzyl-(2-bromoacetyl)amino]but-2-ynoate
• CAS: 899434-28-7
• 化学式: C₁₄H₁₄BrNO₃
• 分子量: 324.174
• InChiKey: YTVOQSNYXZPCLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(N-benzyl-2-bromoacetamido)but-2-ynoate 、 3-氯丙胺盐酸盐 在 四丁基碘化铵 4 A molecular sieve 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 以82%的产率得到2-benzyl-3-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[1,2-a]pyrazine-9-carboxylic acid 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：

  N-benzyl-4-(tert-butyldimethylsilyloxy)but-2-yn-1-amine 在 4-二甲氨基吡啶 、 jones reagent 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 生成 methyl 4-(N-benzyl-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

文献信息

• A sequential reaction process to assemble polysubstituted indolizidines, quinolizidines and quinolizidine analogues
  作者：Guorong Cai、Wei Zhu、Dawei Ma

  DOI：10.1016/j.tet.2006.03.068

  日期：2006.6

  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.