3-(methyl(phenyl)amino)butan-2-ol | 3233-04-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(methyl(phenyl)amino)butan-2-ol
• 英文别名: 3-(N-methylanilino)butan-2-ol
• CAS: 3233-04-3
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: KMXRLARVGQBCAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 以14.3 mg的产率得到3-(methyl(phenyl)amino)butan-2-ol
  参考文献：
  名称：

  通过迭代硼同系化进行可编程胺合成

  摘要：

  可编程胺合成是通过将氮和碳原子顺序插入硼酸CB键来实现的。这一策略是通过一种新的氮烯类试剂实现的，该试剂允许通过N-插入从芳基或烷基硼酸酯直接形成氨基硼烷。

  DOI：

  10.1002/anie.202307118

文献信息

• New domino radical synthesis of aminoalcohols promoted by TiCl4–Zn/t-BuOOH system: selective hydroxyalkylation of amines in alcohol or in cyclic ether cosolvents
  作者：Simona Prosperini、Nadia Pastori、Alessandra Ghilardi、Angelo Clerici、Carlo Punta

  DOI：10.1039/c1ob05191a

  日期：——

  We report a new and fast domino synthesis of aminoalcohols under mild conditions. The free-radical reaction of aliphatic and aromatic amines with alcohol cosolvents is promoted by means of the TiCl4–Zn/t-BuOOH system. According to the proposed mechanism, the amine reacts with two molecules of alcohol in an electrophilic–nucleophilic cascade process. This procedure, if compared with the TiCl3/t-BuOOH-mediated protocol previously reported, appears to be more selective, of more general applicability and affords the desired products in higher yields. Besides, with the same catalytic system it was possible to promote the reaction of primary arylamines with two molecules of cyclic ether, leading to the formation of a wider range of functionalized aminoalcohols.

  我们报告了一种在温和条件下快速合成氨基醇的新型多米诺反应。脂肪族和芳香族胺与醇共溶剂的自由基反应由TiCl4–Zn/t-BuOOH体系促进。根据提出的机理，胺与两个分子的醇反应，形成电亲核级联反应。如果与之前报道的TiCl3/t-BuOOH介导的方案相比，该过程显得更加选择性，适用性更广，并使目标产品的产率更高。此外，利用相同的催化体系，还可以促进初级芳胺与两个分子环醚的反应，从而形成更广泛种类的功能化氨基醇。
• Efficient radical domino approach to β-aminoalcohols from arylamines and alcohols triggered by Ti(III)/t-BuOOH
  作者：Raffaele Spaccini、Alessandra Ghilardi、Nadia Pastori、Angelo Clerici、Carlo Punta、Ombretta Porta

  DOI：10.1016/j.tet.2010.01.039

  日期：2010.3

  We report that an aqueous Ti(III)/t-BuOOH system promotes the efficient domino radical reaction of arylamines with alcohol cosolvents leading to beta-aminoalcohols in good yields, in less than ten minutes at room temperature. The free-radical mechanism according to which the amine reacts with two molecules of the alcohol is discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• Programmable Amine Synthesis via Iterative Boron Homologation
  作者：Qiqiang Xie、Rui Zhang、Guangbin Dong

  DOI：10.1002/anie.202307118

  日期：2023.8.28

  Programmable amine synthesis is realized through sequential insertion of nitrogen and carbon atoms into boronate C−B bonds. This strategy is enabled by a new nitrenoid reagent, which allows for direct formation of aminoboranes from aryl or alkyl boronates via N-insertion.

  可编程胺合成是通过将氮和碳原子顺序插入硼酸CB键来实现的。这一策略是通过一种新的氮烯类试剂实现的，该试剂允许通过N-插入从芳基或烷基硼酸酯直接形成氨基硼烷。