N-(2-methylhexyl)cyclohexanamine | 859819-03-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-methylhexyl)cyclohexanamine
• CAS: 859819-03-7
• 化学式: C₁₃H₂₇N
• 分子量: 197.364
• InChiKey: CWTSUPWVDBCECM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基-1-己烯 、 环己胺 在 2,4,6-Triisopropylthiophenol 、 C₄₂H₄₀F₄IrN₄⁽¹⁺⁾*F₆P^(1-) 作用下， 以 甲苯 为溶剂， 以92%的产率得到N-(2-methylhexyl)cyclohexanamine
  参考文献：
  名称：

  未活化烯烃与伯烷基胺的反马尔科夫尼科夫加氢胺化

  摘要：

  我们在这里报告了一种光催化方法，用于未活化烯烃与伯烷基胺的分子间抗马尔科夫尼科夫加氢胺化，以选择性地提供仲胺产物。这些反应通过胺自由基阳离子 (ARC) 中间体进行，并在铱基光催化剂和芳基硫醇氢原子供体的存在下，在室温下在可见光照射下发生。尽管存在过量烯烃，但观察到仲胺产物的选择性高于叔胺产物，即使仲胺是类似条件下基于 ARC 的烯烃胺化的既定底物。

  DOI：

  10.1021/jacs.9b08746

文献信息

• An efficient and recyclable ionic diphosphine-based Ir-catalyst for hydroaminomethylation of olefins with H₂O as the hydrogen source
  作者：Huan Liu、Da Yang、Dong-Liang Wang、Peng Wang、Yong Lu、VO-Thanh Giang、Ye Liu

  DOI：10.1039/c8cc03431a

  日期：——

  One-pot tandem hydroaminomethylation with H₂O as the hydrogen source was accomplished over an ionic diphosphine-based Ir-catalyst with high efficiency and recyclability.

  使用H₂O作为氢源的一锅式串联羟胺甲基化反应在基于离子双膦基Ir催化剂上高效实现，具有高效性和可循环性。
• Rhodium exchanged ETS-10 and ETS-4: Efficient heterogeneous catalyst for hydroaminomethylation
  作者：N. Sudheesh、Ram S. Shukla

  DOI：10.1016/j.apcata.2014.01.002

  日期：2014.3

  Rhodium exchanged titanosilicates (ETS-10 and ETS-4) were synthesized and found to be efficient and stable catalysts for hydroaminomethylation reaction. The catalyst was highly active and selective towards amine product within lower reaction time of 4 h. 1-Hexene and pyrrolidine were taken as representative substrates for parametric variations using Rh-ETS-10. The increase in pyrrolidine ratio gave some significant information showing a decrease in conversion with increased selectivity. The reason may be the competition between pyrrolidine and 1-hexene for coordination sites in rhodium and which prevents the beta-hydride elimination. The ratios of H-2 and CO have influenced hydroaminomethylation and the best performance was in the CO: H-2 ratio of 1:4 under the studied conditions. The initial rate of formation of amine was double than that of isomerization of 1-hexene. The Rh cluster like complex was formed on treating the catalyst with syn gas. A homogenous-heterogeneous dual nature of Rh was found during hydroaminomethylation. The catalyst was effectively recycled for three times without much loss in its activity and selectivity. (C) 2014 Elsevier B.V. All rights reserved.
• Rhodium complex encapsulated functionalized hexagonal mesoporous silica for heterogeneous hydroaminomethylation
  作者：N. Sudheesh、Ram S. Shukla

  DOI：10.1016/j.apcata.2012.12.021

  日期：2013.2

  HRh(CO)(PPh3)(3) complex was encapsulated into the pores of amino functionalized hexagonal mesoporous silica. The catalyst was characterized by physico-chemical techniques like P-XRD, P-31-CPMAS NMR, FT-IR, SEM, ICP and N-2 adsorption analysis. The catalyst was active for hydroaminomethylation and a variety of alkenes and amines were used as reactants for hydroaminomethylation. The catalyst afforded to achieve 100% conversion with high (>95%) selectivity to corresponding amines. Parametric variations were performed by taking 1-hexene and morpholine as representative reactants for the study of catalyst amount, temperature, pressure and 1-hexene:morpholine ratio. Significant amounts of aldehydes and enamines were observed during the course of the reaction indicating that there could be two possible rate determining steps. The catalyst was effectively recycled up to five times without much loss in its activity and selectivity. (C) 2012 Elsevier B.V. All rights reserved.
• US4459424A
  申请人：——

  公开号：US4459424A

  公开（公告）日：1984-07-10
• Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines
  作者：David C. Miller、Jacob M. Ganley、Andrew J. Musacchio、Trevor C. Sherwood、William R. Ewing、Robert R. Knowles

  DOI：10.1021/jacs.9b08746

  日期：2019.10.23

  hydroamination of unactivated olefins with primary alkyl amines to selectively furnish secondary amine products. These reactions proceed through aminium radical cation (ARC) intermediates and occur at room temperature under visible light irradiation in the presence of an iridium-based photocatalyst and an aryl thiol hydrogen atom donor. Despite the presence of excess olefin, high selectivities are observed for

  我们在这里报告了一种光催化方法，用于未活化烯烃与伯烷基胺的分子间抗马尔科夫尼科夫加氢胺化，以选择性地提供仲胺产物。这些反应通过胺自由基阳离子 (ARC) 中间体进行，并在铱基光催化剂和芳基硫醇氢原子供体的存在下，在室温下在可见光照射下发生。尽管存在过量烯烃，但观察到仲胺产物的选择性高于叔胺产物，即使仲胺是类似条件下基于 ARC 的烯烃胺化的既定底物。