1-(2-甲基戊基)哌啶 | 16627-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-(2-甲基戊基)哌啶
• 英文名称: 2-methyl-1-pentylpiperidine
• 英文别名: 1-(2-Methylpentyl)piperidine
• CAS: 16627-38-6
• 化学式: C₁₁H₂₃N
• 分子量: 169.31
• InChiKey: VFLGQRXWLFTVQC-UHFFFAOYSA-N

物化性质

• 沸点：
  208.1±8.0 °C(Predicted)
• 密度：
  0.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  哌啶 、 反-2-戊烯 、 一氧化碳 在 Rh(IMes)(cod)Cl 、 氢气 作用下， 以 四氢呋喃 为溶剂， 85.0 ℃ 、6.0 MPa 条件下， 反应 12.0h， 生成 1-(2-乙基丁基)-哌啶 、 1-(2-甲基戊基)哌啶
  参考文献：
  名称：

  Hydroaminomethylation of olefins using a rhodium carbene catalyst

  摘要：

  Hydroaminomethylation of terminal as well as internal aliphatic and aromatic olefins with various amines is described in the presence of [Rh(cod)(Imes)Cl] as a catalyst. In general good to excellent yields and high chemo selectivity were obtained in THF at 85-105degreesC using 0.1 mol% of catalyst. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)00008-x

文献信息

• Highly Selective Hydroaminomethylation of Internal Alkenes To Give Linear Amines
  作者：Moballigh Ahmed、Raymond P. J. Bronger、Ralf Jackstell、Paul C. J. Kamer、Piet W. N. M. van Leeuwen、Matthias Beller

  DOI：10.1002/chem.200600702

  日期：2006.12.4

  internal olefins and mixtures of internal and terminal olefins have been converted highly selectively into linear amines. Investigations of the effects of the calculated natural bite angles of ligands on hydroaminomethylation shows that the regioselectivity for the linear product follows a similar trend to that seen in the hydroformylation of internal alkenes with the aid of these ligands. Hydroaminomethylation

  据报道，苯氧磷膦改性的Xantphos型配体（1-9）在铑催化的内烯烃加氢氨基甲基化反应中得到线性胺。通过使用0.1摩尔％[Rh（cod）2] BF（4）/0.4摩尔％黄嘌呤草磷（1）获得了出色的化学和区域选择性，为从内部制备胺提供了实用且对环境有吸引力的合成途径烯烃。第一次，官能化的内烯烃以及内烯烃和末端烯烃的混合物都被高度选择性地转化为线性胺。对所计算的配体的自然咬合角对氢氨基甲基化的影响的研究表明，线性产物的区域选择性遵循与借助这些配体的内部烯烃的氢甲酰化所观察到的趋势相似的趋势。通过高压红外光谱法监测氢氨基甲基化及其各个步骤。结果表明，氢氨基甲基化通过顺序异构化/加氢甲酰化/胺化/加氢途径发生。
• Rhodium-catalyzed regioselective hydroaminomethylation of terminal olefins with pyrrole-based tetraphosphorus ligands
  作者：Guodu Liu、Zhao Li、Huiling Geng、Xumu Zhang

  DOI：10.1039/c3cy01069d

  日期：——

  developed to prepare linear amines by regioselective hydroaminomethylation of terminal olefins with pyrrole-based tetraphosphorus ligands. It has been documented that the reactivity of the ligand is modulated by the substituent of the biphenylphosphane moiety. Ligand L5 containing electron-donating groups exhibited the highest reactivity, with up to 70.9 n/i ratio and 99.5% amine selectivity for 1-pentene

  通过使用基于吡咯的四磷配体的末端烯烃的区域选择性氢氨基甲基化，开发了一种简洁优雅的方法来制备线性胺。已经证明，配体的反应性是由联苯膦部分的取代基调节的。含给电子基团的配体L5表现出最高的反应性，对1-戊烯的比率高达70.9 n / i，胺选择性为99.5％，对1-己烯的比率为31.3 n / i，胺选择性为97.9％。
• Efficient and Regioselective Ruthenium-catalyzed Hydro-aminomethylation of Olefins
  作者：Lipeng Wu、Ivana Fleischer、Ralf Jackstell、Matthias Beller

  DOI：10.1021/ja312271c

  日期：2013.3.13

  An efficient and regioselective ruthenium-catalyzed hydroaminomethlyation of olefins is reported. Key to success is the use of specific 2-phosphino-substituted imidazole ligands and triruthenium dodecacarbonyl as catalyst. Both industrially important aliphatic as well as various functionalized olefins react with primary and secondary amines to give the corresponding secondary and tertiary amines generally in high yields (up to 96%) and excellent regioselectivities (n/iso up to 99:1).
• Amines Made Easily:  A Highly Selective Hydroaminomethylation of Olefins
  作者：Moballigh Ahmed、Abdul Majeed Seayad、Ralf Jackstell、Matthias Beller

  DOI：10.1021/ja030143w

  日期：2003.8.1

  A highly chemo- and regioselective hydroaminomethylation of simple as well as functionalized alpha-olefins using a cationic rhodium precatalyst together with Xantphos as ligand is reported. Studies of the influence of ligands and reaction conditions led to an unprecedented selective hydroaminomethylation procedure. The novel procedure constitutes an economically attractive and environmentally favorable synthesis of secondary and tertiary aliphatic amines.