4-fluoro-N-(4-methyl-1-phenylpent-3-enyl)aniline | 1187159-22-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-fluoro-N-(4-methyl-1-phenylpent-3-enyl)aniline
• CAS: 1187159-22-3
• 化学式: C₁₈H₂₀FN
• 分子量: 269.362
• InChiKey: DPZPKCBMCDMQFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-benzylidene-4-fluoroaniline 、 1-溴-3-甲基-2-丁烯 在 锌 作用下， 以 四氢呋喃 、 1,3-二甲基-2-咪唑啉酮 为溶剂， 反应 16.0h， 以90%的产率得到4-fluoro-N-(4-methyl-1-phenylpent-3-enyl)aniline
  参考文献：
  名称：

  Zinc-Mediated Highly α-Regioselective Prenylation of Imines with Prenyl Bromide

  摘要：

  A highly alpha-regioselective prenylation of imines has been successfully developed. The efficiency of this approach is confirmed by a wide range of imines including N- and C-aryl aldimines, N-alkyl aldimines, C-alkyl aldimines, and N- and C-aryl ketimines. The approach uses prenyl bromide as the prenyl source and inexpensive and convenient zinc as the mediator as well as environmentally benign 1,3-dimethyl-2-imidazolidinone (DMI) as the solvent.

  DOI：

  10.1021/ol203410m

文献信息

• Generation of Prenylhafnium and α-Selective Addition to Imines
  作者：Ikuya Shibata、Shinji Miyamoto、Shinji Tsunoi、Kazuya Sakamoto、Akio Baba

  DOI：10.1002/ejoc.200900445

  日期：2009.7

  Allylhafnium compounds were generated by transmetalation between allyl-SnBu3 and HfCl4 in EtCN. A highly α-selective addition reaction of prenyltributyltin to imines was observed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  烯丙基铪化合物是通过烯丙基-SnBu3 和 HfCl4 在 EtCN 中的金属转移生成的。观察到异戊二烯三丁基锡与亚胺的高度α-选择性加成反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Zinc-Mediated Highly α-Regioselective Prenylation of Imines with Prenyl Bromide
  作者：Li-Ming Zhao、Shu-Qing Zhang、Hai-Shan Jin、Li-Jing Wan、Fei Dou

  DOI：10.1021/ol203410m

  日期：2012.2.3

  A highly alpha-regioselective prenylation of imines has been successfully developed. The efficiency of this approach is confirmed by a wide range of imines including N- and C-aryl aldimines, N-alkyl aldimines, C-alkyl aldimines, and N- and C-aryl ketimines. The approach uses prenyl bromide as the prenyl source and inexpensive and convenient zinc as the mediator as well as environmentally benign 1,3-dimethyl-2-imidazolidinone (DMI) as the solvent.