3-(12-bromo-dodec-9-enyl)-pyridine | 466639-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(12-bromo-dodec-9-enyl)-pyridine
• 英文别名: 3-[(E)-12-bromododec-9-enyl]pyridine
• CAS: 466639-79-2
• 化学式: C₁₇H₂₆BrN
• 分子量: 324.304
• InChiKey: QRPJQIQOOVRWTE-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(12-bromo-dodec-9-enyl)-pyridine 在 sodium azide 、 三苯基膦 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (12-pyridin-3-yl-dodec-3-enyl)-carbamic acid tert-butylester
  参考文献：
  名称：

  Synthesis of the Cytotoxic Sponge Metabolite Haliclamine A

  摘要：

  A new convergent and unified synthesis of the marine natural alkaloid haliclamine A is described. The synthesis of 3-alkylpyridine monomers 8 and 9 was first achieved from a common thiophene intermediate 5. These syntheses make use of thiophene chemistry and the ability of cyclopropylcarbinols 20 and 21 to rearrange to the homoallylic bromides 22 and 23, respectively. The Zincke procedure for the synthesis of pyridinium salts was then applied to the corresponding amino derivatives 8 and 9 to give efficiently unsymmetrical bis-pyridinium macrocycle 1, whose reduction afforded haliclamine A.

  DOI：

  10.1021/jo025650v
• 作为产物：
  描述：

  2-噻酚基环丙基甲酮 在 镍 咪唑 、 sodium tetrahydroborate 、 正丁基锂 、 三甲基溴硅烷 、 四丁基氟化铵 、 sodium hydride 、 sodium carbonate 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.75h， 生成 3-(12-bromo-dodec-9-enyl)-pyridine
  参考文献：
  名称：

  Synthesis of the Cytotoxic Sponge Metabolite Haliclamine A

  摘要：

  A new convergent and unified synthesis of the marine natural alkaloid haliclamine A is described. The synthesis of 3-alkylpyridine monomers 8 and 9 was first achieved from a common thiophene intermediate 5. These syntheses make use of thiophene chemistry and the ability of cyclopropylcarbinols 20 and 21 to rearrange to the homoallylic bromides 22 and 23, respectively. The Zincke procedure for the synthesis of pyridinium salts was then applied to the corresponding amino derivatives 8 and 9 to give efficiently unsymmetrical bis-pyridinium macrocycle 1, whose reduction afforded haliclamine A.

  DOI：

  10.1021/jo025650v

文献信息

• Synthesis of the Cytotoxic Sponge Metabolite Haliclamine A
  作者：Sophie Michelliza、Ali Al-Mourabit、Alice Gateau-Olesker、Christian Marazano

  DOI：10.1021/jo025650v

  日期：2002.9.1

  A new convergent and unified synthesis of the marine natural alkaloid haliclamine A is described. The synthesis of 3-alkylpyridine monomers 8 and 9 was first achieved from a common thiophene intermediate 5. These syntheses make use of thiophene chemistry and the ability of cyclopropylcarbinols 20 and 21 to rearrange to the homoallylic bromides 22 and 23, respectively. The Zincke procedure for the synthesis of pyridinium salts was then applied to the corresponding amino derivatives 8 and 9 to give efficiently unsymmetrical bis-pyridinium macrocycle 1, whose reduction afforded haliclamine A.