2-(3,5-dimethylanilino)-3-buten-1-ol | 1446417-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,5-dimethylanilino)-3-buten-1-ol
• 英文别名: 2-(3,5-Dimethylanilino)but-3-en-1-ol；2-(3,5-dimethylanilino)but-3-en-1-ol
• CAS: 1446417-54-4
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: JANHJBPHCOPHNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二氢呋喃 、 1-氨基-3,5-二甲苯 在 zinc trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以66%的产率得到2-(3,5-dimethylanilino)-3-buten-1-ol
  参考文献：
  名称：

  Zn(CF3SO3)2—mediated domino hydroamination-ring cleavage of 2,5-dihydrofuran

  摘要：

  By using Zn(CF3SO3)(2) as the catalyst, series of 2-arylamino-3-buten-1-ols (3) were successfully synthesized via domino hydroamination-ring cleavage of 2,5-dihydrofuran (1) with aromatic amines (2). A proton-induced and Zn(CF3SO3)(2)-assisted mechanism is proposed on the experimental basis, during which the proton is generated by the interaction between aniline and Zn(CF3SO3)(2). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.058

文献信息

• Stereoselective and Versatile Preparation of Tri- and Tetrasubstituted Allylic Amine Scaffolds under Mild Conditions
  作者：Wusheng Guo、Luis Martínez-Rodríguez、Rositha Kuniyil、Eddy Martin、Eduardo C. Escudero-Adán、Feliu Maseras、Arjan W. Kleij

  DOI：10.1021/jacs.6b07382

  日期：2016.9.14

  observed in recent years in the synthesis of allylic amines, which are important building blocks in synthetic chemistry. Most of these processes are effective toward the preparation of allylic amines, with limited potential to introduce three or four different substituents on the olefinic unit in a stereocontrolled fashion. Therefore, the discovery of a mild and operationally simple protocol allowing

  近年来，烯丙胺的合成取得了重大进展，烯丙胺是合成化学的重要组成部分。大多数这些方法对于制备烯丙胺是有效的，但以立体控制的方式在烯烃单元上引入三个或四个不同的取代基的潜力有限。因此，发现一种温和且操作简单的方案，允许多取代烯丙胺的这种具有挑战性的立体选择性合成仍然是一个鼓舞人心的目标。在此，我们报告了基于 Pd 催化转化的烯丙基替代物的立体选择性合成三和四取代烯丙胺的第一个通用和实用的方法，这些烯丙基替代物很容易从环状碳酸乙烯酯中获得。这些罕见的转化具有出色的立体选择性，操作简单，反应条件温和，反应对象范围广。进行了 DFT 研究以合理化这些烯丙胺形成反应中的立体控制，并提供证据表明六元钯环中间体的形成导致形成 (Z) 构型的烯丙胺产物。
• Zn(CF3SO3)2—mediated domino hydroamination-ring cleavage of 2,5-dihydrofuran
  作者：Xiao-juan Shen、Hong-zhong Bu、Jie Shi、Zheng-guang Wu、Hong-fei Ma、Yu-feng Li

  DOI：10.1016/j.tetlet.2013.05.058

  日期：2013.7

  By using Zn(CF3SO3)(2) as the catalyst, series of 2-arylamino-3-buten-1-ols (3) were successfully synthesized via domino hydroamination-ring cleavage of 2,5-dihydrofuran (1) with aromatic amines (2). A proton-induced and Zn(CF3SO3)(2)-assisted mechanism is proposed on the experimental basis, during which the proton is generated by the interaction between aniline and Zn(CF3SO3)(2). (C) 2013 Elsevier Ltd. All rights reserved.