2-甲基-8-壬烯-4-胺 | 350236-98-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-甲基-8-壬烯-4-胺
• 英文名称: 2-methyl-8-nonen-4-amine
• 英文别名: 8-Nonen-4-amine, 2-methyl-；2-methylnon-8-en-4-amine
• CAS: 350236-98-5
• 化学式: C₁₀H₂₁N
• 分子量: 155.283
• InChiKey: PQKZGNPMZOCNLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-甲基-8-壬烯-4-胺 在 Cp*2NdCH(SiMe₃)2 作用下， 以 氘代苯 为溶剂， 反应 14.0h， 以97%的产率得到(2R*,6R*)-2-iso-butyl-6-methylpiperidine
  参考文献：
  名称：

  A Diastereoselective Intramolecular Hydroamination Approach to the Syntheses of (+)-, (±)-, and (−)-Pinidinol

  摘要：

  A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)(2) converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100:1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.

  DOI：

  10.1021/jo015603n
• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 在 三苯基膦 、 甲胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 49.0h， 生成 2-甲基-8-壬烯-4-胺
  参考文献：
  名称：

  A Diastereoselective Intramolecular Hydroamination Approach to the Syntheses of (+)-, (±)-, and (−)-Pinidinol

  摘要：

  A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)(2) converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100:1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.

  DOI：

  10.1021/jo015603n

文献信息

• A Diastereoselective Intramolecular Hydroamination Approach to the Syntheses of (+)-, (±)-, and (−)-Pinidinol
  作者：Gary A. Molander、Eric D. Dowdy、Shawn K. Pack

  DOI：10.1021/jo015603n

  日期：2001.6.1

  A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)(2) converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100:1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.