N-allyl-N-(1-(2-bromophenyl)-3-oxopropyl)pent-4-enamide | 1309612-20-1

• 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: N-allyl-N-(1-(2-bromophenyl)-3-oxopropyl)pent-4-enamide
• CAS: 1309612-20-1
• 化学式: C₁₇H₂₀BrNO₂
• 分子量: 350.255
• InChiKey: WTJJZHGGUKUWFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(1-(2-bromophenyl)-3-oxopropyl)pent-4-enamide 在 盐酸 、 二(三叔丁基膦)钯 、 碘 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 17.5h， 生成 (1SR,9Z,12RS,16SR)-15-methyl-N-(2-phenylethyl)-14-oxa-8-thia-10,15-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-2(7),3,5-trien-9-imine
  参考文献：
  名称：

  Multicomponent Assembly and Diversification of Novel Heterocyclic Scaffolds Derived from 2-Arylpiperidines

  摘要：

  A collection of structurally diverse, polyheterocyclic scaffolds comprising a 2-arylpiperidine subunit were synthesized using a Mannich-type multicomponent assembly process, followed by appropriately sequenced ring-forming reactions. An Improved procedure for removal of N-4-pentenoyl groups was developed; one-pot sequences for tandem urea/thiourea formation and cyclization and tandem enolate arylation/alkylation were discovered. A novel entry to bridged tetrahydroquinoline scaffolds exploiting A(1,3) strain was also invented. Derivatization of several scaffolds was achieved by cross-coupling and N-functionalization.

  DOI：

  10.1021/ol201010s
• 作为产物：
  描述：

  邻溴苯甲醛 在 三氟甲磺酸三甲基硅酯 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 N-allyl-N-(1-(2-bromophenyl)-3-oxopropyl)pent-4-enamide
  参考文献：
  名称：

  Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives

  摘要：

  A multicomponent, Mannich-type assembly process commencing with commercially available bromobenzaldehydes was sequenced with [3+2] dipolar cycloaddition reactions involving nitrones and azomethine ylides to generate collections of fused, bicyclic scaffolds based on the 2-arylpiperidine subunit. Use of the 4-pentenoyl group, which served both as an activator in the Mannich-type reaction and a readily-cleaved amine protecting group, allowed sub-libraries to be prepared through piperidine N-functionalization and cross-coupling of the aryl bromide. A number of these derivatives displayed biological activities that had not previously been associated with this substructure. Methods were also developed that allowed rapid conversion of these scaffolds to novel, polycyclic dihydroquinazolin-2-ones, 2-imino-1,3-benzothiazinanes, dihydroisoquinolin-3-ones, and bridged tetrahydroquinolines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.045