4-methoxy-N-(4-methyl-1-phenylpent-3-en-1-yl)aniline | 1187159-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxy-N-(4-methyl-1-phenylpent-3-en-1-yl)aniline
• 英文别名: 4-methoxy-N-(4-methyl-1-phenylpent-3-enyl)aniline
• CAS: 1187159-24-5
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: VRAWSRXKYYUJEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(4-methyl-1-phenylpent-3-en-1-yl)aniline 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 以49 %的产率得到7-methoxy-5,5-dimethyl-2-phenyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine
  参考文献：
  名称：

  二烯和酮的双催化分子间还原偶联**

  摘要：

  报道了一种温和的催化方法，用于原料二烯和苯乙烯与酮和亚胺的分子间还原偶联。这种简单方法的应用包括药物分子的有效合成和位点选择性后期功能化。

  DOI：

  10.1002/anie.202314870
• 作为产物：
  描述：

  N-亚苄基-4-甲氧基苯胺 、 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91%的产率得到4-methoxy-N-(4-methyl-1-phenylpent-3-en-1-yl)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.
• Dual‐Catalysed Intermolecular Reductive Coupling of Dienes and Ketones**
  作者：Victor J. Mayerhofer、Martina Lippolis、Christopher J. Teskey

  DOI：10.1002/anie.202314870

  日期：2024.1.8

  A mild, catalytic method for the intermolecular reductive coupling of feedstock dienes and styrenes with ketones and imines is reported. Applications of this straightforward approach include the efficient synthesis of drug molecules and site-selective late-stage functionalisation.

  报道了一种温和的催化方法，用于原料二烯和苯乙烯与酮和亚胺的分子间还原偶联。这种简单方法的应用包括药物分子的有效合成和位点选择性后期功能化。