exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile | 1003194-36-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile
• 英文别名: 2-(4-(8-methyl-8-azabicyclo[ 3.2.1]octan-3-yl)phenyl)acetonitrile
• CAS: 1003194-36-2
• 化学式: C₁₆H₂₀N₂
• 分子量: 240.348
• InChiKey: TWPNZZZPMNQTJX-PHZGNYQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  27.03
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-tropanol 在 氯化亚砜 、 二异丁基氢化铝 、 magnesium 、 lithium chloride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 93.25h， 生成 exo-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl]acetonitrile
  参考文献：
  名称：

  Direct Aminoalkylation of Arenes, Heteroarenes, and Alkenes via Ni-Catalyzed Negishi Cross-Coupling Reactions

  摘要：

  A room-temperature Ni-catalyzed cross-coupling of aryl, heteroaryl, and alkenyl electrophiles with aminoalkylzinc bromides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, was developed. The reaction allows a convenient one-step preparation of various aminoalkyl products, including piperidine and tropane derivatives. Such functionalized amine moieties are widely present in various biologically active molecules. Aryl, heteroaryl, and alkenyl iodides, bromides, chlorides and triflates are suitable electrophiles. A short total synthesis of two natural products, (+/-)-galipinine and (+/-)-cusparine, is also reported.

  DOI：

  10.1021/jo201630e

文献信息

• Direct Aminoalkylation of Arenes and Hetarenes via Ni-Catalyzed Negishi Cross-Coupling Reactions
  作者：Laurin Melzig、Andrey Gavryushin、Paul Knochel

  DOI：10.1021/ol702499h

  日期：2007.12.1

  room-temperature Ni-catalyzed cross-coupling of aminoalkylzinc halides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, with aryl and hetaryl electrophiles, allows a convenient one-step preparation of aminoalkyl (het)arenes, bearing a basic tertiary nitrogen in the side chain, including piperidine and tropane derivatives. Such aminoalkylarene scaffolds are widely present in

  氨基烷基锌卤化物的直接室温Ni催化交叉偶联很容易从相应的氨基烷基氯化物通过Grignard试剂与芳基和杂芳基亲电试剂获得，可以方便地一步制备带有碱性叔胺的氨基烷基（杂）芳烃侧链中的氮包括哌啶和托烷衍生物。这种氨基烷基亚芳基支架广泛存在于各种生物活性分子中。