2-methyl-2-(p-tolylamino)hexan-1-ol | 1413925-41-3

• 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-methyl-2-(p-tolylamino)hexan-1-ol
• 英文别名: 2-Methyl-2-(4-methylanilino)hexan-1-ol；2-methyl-2-(4-methylanilino)hexan-1-ol
• CAS: 1413925-41-3
• 化学式: C₁₄H₂₃NO
• 分子量: 221.343
• InChiKey: YUWRLNUPHOLMDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  甲醇 、 2-己酮 、 乙烷,三氯氟- 在 叔丁基过氧化氢 、 四氯化钛 、 锌 作用下， 以 水 为溶剂， 以60%的产率得到2-methyl-2-(p-tolylamino)hexan-1-ol
  参考文献：
  名称：

  Free-radical hydroxymethylation of ketimines generated in situ: a one-pot multicomponent synthesis of β,β-disubstituted-β-aminoalcohols

  摘要：

  We report how an acidic TiCl4-Zn/t-BuOOH system is able to promote the one-pot multicomponent synthesis of beta,beta-disubstituted-beta-aminoalcohols via nucleophilic addition of a hydroxymethyl radical to activated ketimines generated in situ in methanol solvent. While ketimines are generally recognized as less reactive and less stable when compared with aldimines, Ti(IV) plays a key role in facilitating their formation and in enhancing their electrophilic character. As a consequence, the reaction occurs at room temperature and under non-anhydrous conditions in just 1 h, without requiring either the preformation of the ketimine or protection of the amino group. The scope of the reaction is widely explored and a possible mechanism is discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.107

文献信息

• Free-radical hydroxymethylation of ketimines generated in situ: a one-pot multicomponent synthesis of β,β-disubstituted-β-aminoalcohols
  作者：Bianca Rossi、Nadia Pastori、Angelo Clerici、Carlo Punta

  DOI：10.1016/j.tet.2012.09.107

  日期：2012.12

  We report how an acidic TiCl4-Zn/t-BuOOH system is able to promote the one-pot multicomponent synthesis of beta,beta-disubstituted-beta-aminoalcohols via nucleophilic addition of a hydroxymethyl radical to activated ketimines generated in situ in methanol solvent. While ketimines are generally recognized as less reactive and less stable when compared with aldimines, Ti(IV) plays a key role in facilitating their formation and in enhancing their electrophilic character. As a consequence, the reaction occurs at room temperature and under non-anhydrous conditions in just 1 h, without requiring either the preformation of the ketimine or protection of the amino group. The scope of the reaction is widely explored and a possible mechanism is discussed. (C) 2012 Elsevier Ltd. All rights reserved.