2-(2-chloroethyl)-1-methyl-1,2,3,4-tetrahydroquinoline | 1338057-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(2-chloroethyl)-1-methyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 2-(2-chloroethyl)-1-methyl-3,4-dihydro-2H-quinoline
• CAS: 1338057-34-3
• 化学式: C₁₂H₁₆ClN
• 分子量: 209.719
• InChiKey: GZKYQLAMMCGLGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-溴黎芦醚 、 2-(2-chloroethyl)-1-methyl-1,2,3,4-tetrahydroquinoline 在 二异丁基氢化铝 、 magnesium 、 lithium chloride 、 zinc dibromide 、 bis(acetylacetonate)nickel(II) 、 双(2-二苯基磷苯基)醚 作用下， 以 四氢呋喃 为溶剂， 反应 19.25h， 以548 mg的产率得到cuspareine
  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
• 作为产物：
  描述：

  2-(2-羟基甲基)喹啉 在 sodium tetrahydroborate 、 氯化亚砜 、 sodium cyanoborohydride 、 溶剂黄146 、 nickel dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 2-(2-chloroethyl)-1-methyl-1,2,3,4-tetrahydroquinoline
  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