(2-Bromo-allyl)-hexyl-trimethylsilanyl-amine | 153476-56-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2-Bromo-allyl)-hexyl-trimethylsilanyl-amine
• 英文别名: N-(2-bromoprop-2-enyl)-N-trimethylsilylhexan-1-amine
• CAS: 153476-56-3
• 化学式: C₁₂H₂₆BrNSi
• 分子量: 292.335
• InChiKey: JIOHFLVFNWOEFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-Bromo-allyl)-hexyl-trimethylsilanyl-amine 生成 N-Hexyl-2-deuterioallylamine
  参考文献：
  名称：

  Preparation and reactivity of new .beta.-nitrogen-functionalized vinylic organolithium compounds from secondary aliphatic allylamines

  摘要：

  Two new types of B-nitrogen-functionalized vinylic organolithium compounds have been prepared from secondary aliphatic allylamines through the temporary silylation of the amino group. The monoanionic intermediates 4, stable at -80 degrees C, are generated by a bromine-lithium exchange reaction and the dianionic derivatives 2, stable at room temperature, by a tin-lithium transmetalation reaction. Both types of organolithium compounds react with different electrophiles giving functionalized allylamines 7 and 10-27. Moreover, dianionic derivatives 30, 33 can be prepared directly by bromine-lithium exchange when the beta-elimination reaction of hydrogen bromide in the lithium 2-bromoallylamide is structurally hindered. Additionally, a novel type of anionic 1,3-rearrangement of a trimethylsilyl group from nitrogen to carbon is described.

  DOI：

  10.1021/jo00082a017
• 作为产物：
  描述：

  正己胺 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 (2-Bromo-allyl)-hexyl-trimethylsilanyl-amine
  参考文献：
  名称：

  Preparation and reactivity of new .beta.-nitrogen-functionalized vinylic organolithium compounds from secondary aliphatic allylamines

  摘要：

  Two new types of B-nitrogen-functionalized vinylic organolithium compounds have been prepared from secondary aliphatic allylamines through the temporary silylation of the amino group. The monoanionic intermediates 4, stable at -80 degrees C, are generated by a bromine-lithium exchange reaction and the dianionic derivatives 2, stable at room temperature, by a tin-lithium transmetalation reaction. Both types of organolithium compounds react with different electrophiles giving functionalized allylamines 7 and 10-27. Moreover, dianionic derivatives 30, 33 can be prepared directly by bromine-lithium exchange when the beta-elimination reaction of hydrogen bromide in the lithium 2-bromoallylamide is structurally hindered. Additionally, a novel type of anionic 1,3-rearrangement of a trimethylsilyl group from nitrogen to carbon is described.

  DOI：

  10.1021/jo00082a017

文献信息

• Preparation and reactivity of new .beta.-nitrogen-functionalized vinylic organolithium compounds from secondary aliphatic allylamines
  作者：Jose Barluenga、Rosa Maria Canteli、Josefa Florez

  DOI：10.1021/jo00082a017

  日期：1994.2

  Two new types of B-nitrogen-functionalized vinylic organolithium compounds have been prepared from secondary aliphatic allylamines through the temporary silylation of the amino group. The monoanionic intermediates 4, stable at -80 degrees C, are generated by a bromine-lithium exchange reaction and the dianionic derivatives 2, stable at room temperature, by a tin-lithium transmetalation reaction. Both types of organolithium compounds react with different electrophiles giving functionalized allylamines 7 and 10-27. Moreover, dianionic derivatives 30, 33 can be prepared directly by bromine-lithium exchange when the beta-elimination reaction of hydrogen bromide in the lithium 2-bromoallylamide is structurally hindered. Additionally, a novel type of anionic 1,3-rearrangement of a trimethylsilyl group from nitrogen to carbon is described.