3-(p-tolylamino)butan-2-ol | 1358822-49-7

• 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: 3-(p-tolylamino)butan-2-ol
• 英文别名: 3-(4-Methylanilino)butan-2-ol
• CAS: 1358822-49-7
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: PCIOJWJKROKDJP-UHFFFAOYSA-N

物化性质

• 沸点：
  309.3±17.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二甲基环氧乙烷 、 乙烷,三氯氟- 在 Ni(II) complex of poly(vinyl chloride)-supported 2-[(2-aminoethylimino)methyl]phenol 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以80%的产率得到3-(p-tolylamino)butan-2-ol
  参考文献：
  名称：

  Synthesis of β-amino alcohols catalyzed by poly(vinyl chloride)-supported Schiff base metal complexes

  摘要：

  Eight transition metal complexes of various Schiff bases supported on poly(vinyl chloride) (PVC) were prepared and characterized. These metal complexes were screened as heterogeneous catalysts in the synthesis of beta-amino alcohols by ring opening of epoxides with amines. The best catalyst was identified as a Ni(II) complex of PVC-supported 2-[(2-aminoethylimino)methyl]phenol and it was used in the synthesis of a number of different beta-amino alcohols. The catalyst was found to be reusable for up to five cycles.

  DOI：

  10.1007/s00706-011-0628-x

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。
• Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols
  作者：Bianca Rossi、Nadia Pastori、Simona Prosperini、Carlo Punta

  DOI：10.3762/bjoc.11.10

  日期：——

  aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs under mild conditions by mediation of the TiCl4/Zn/t-BuOOH system, leading to the formation of quaternary beta-amino-ethers and -alcohols. The new reaction conditions guarantee good selectivity by preventing

  按照优化的多组分程序，通过将酮基与原位生成的酮亚胺基团进行亲核基团加成，可以在一锅合成中组装芳基胺，酮和环状醚或醇分子。该反应在温和条件下通过TiCl4 / Zn / t-BuOOH系统的介导而发生，从而导致季铵化β-氨基醚和-醇的形成。新的反应条件通过防止副产物的形成，确保了良好的选择性。次级产物可能源自竞争性多米诺骨牌反应，该反应涉及酮基自由基的进一步氧化。
• Enantioselective syntheses of β-amino alcohols catalyzed by recyclable chiral Fe(<scp>iii</scp>) metal complex
  作者：Rajkumar Tak、Manish Kumar、Rukhsana I. Kureshy、Manoj Kumar Choudhary、Noor-ul H. Khan、Sayed H. R. Abdi、Hari C. Bajaj

  DOI：10.1039/c5ra23600b

  日期：——

  meso-epoxides with anilines catalysed by a series of simple and environmentally benign in situ generated Fe(III) complexes based on chiral tridentate ligands L1–L7 with achiral and chiral linkers (methylene, piperazine, R/S BINOL and diethyl tartrate) was carried out at rt. The in situ generated iron metal complex based on ligand L5a emerged as improved (low catalyst loading) catalyst for asymmetric desymmetrization

  的有效非对称desymmetrization内消旋环氧化物与由一系列简单的和对环境无害的催化苯胺原位生成的Fe（III）络合物基于手性三齿配体大号1 -L 7与非手性和手性接头（亚甲基，哌嗪，[R /小号在室温下进行BINOL和酒石酸二乙酯）。该原位生成的铁金属络合物基于配体大号5一个成为改善（低催化剂载量）的催化剂用于不对称desymmetrization内消旋苯胺的β-环氧化物在14小时内可提供高对映选择性（高达99％）和高产率（95％）的对映纯β-氨基醇。用配体L 4 h和氯化Fe（III）原位生成的配合物可获得环状和脂肪族环氧化物与苯胺的ARO优异结果，该催化剂可回收和循环使用（5次），并保持其性能。
• 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.
• ALCAIDE, B.;MARDOMINGO, C. L.;PEREZ-OSSORIO, R.;PLUMET, J.;PHAN-TAN-LUU, +, CAN. J. CHEM., 1985, 63, N 8, 2241-2244
  作者：ALCAIDE, B.、MARDOMINGO, C. L.、PEREZ-OSSORIO, R.、PLUMET, J.、PHAN-TAN-LUU, +

  DOI：——

  日期：——