N-[1-(4-bromophenyl)ethyl]-4-methylaniline | 1021086-20-3

• 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: N-[1-(4-bromophenyl)ethyl]-4-methylaniline
• CAS: 1021086-20-3
• 化学式: C₁₅H₁₆BrN
• 分子量: 290.203
• InChiKey: NHXGMHFIUVOOTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-(4-bromophenyl)-N-(p-tolyl)ethan-1-imine 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以97%的产率得到N-[1-(4-bromophenyl)ethyl]-4-methylaniline
  参考文献：
  名称：

  聚甲基羟基硅氧烷和[RuCl2（arene）] 2催化剂通过亚胺的轻度催化氢化硅烷化合成胺

  摘要：

  耐硅胶！稳定的[RuCl 2（p- cymene）2络合物是一种有效的催化剂，可使用聚甲基羟基硅氧烷作为廉价，稳定且安全的氢化硅烷源，将官能化的亚胺和酮亚胺直接化学选择性氢化硅烷化为胺。在室温下，并能耐受酮酯和烯烃的官能团。

  DOI：

  10.1002/cssc.201100585

文献信息

• Iron-Catalyzed Reductive Coupling of Nitroarenes with Olefins: Intermediate of Iron–Nitroso Complex
  作者：Heng Song、Zhuoyi Yang、Chen-Ho Tung、Wenguang Wang

  DOI：10.1021/acscatal.9b03604

  日期：2020.1.3

  Using a single half-sandwich iron(II) compound, Cp*Fe(1,2-Ph2PC6H4S)(NCMe) (Cp*– = C5Me5–, 1) as a catalyst, reductive coupling of nitroarenes with olefins has been achieved by a well-defined iron(II)/(EtO)3SiH system. Through either inter- or intramolecular reductive coupling, various branched amines and indole derivatives have been directly synthesized in one-pot. Mechanistic studies showed that

  使用单一的半夹心铁（II）化合物作为催化剂，将Cp * Fe（1,2-Ph 2 PC 6 H 4 S）（NCMe）（Cp * – = C 5 Me 5 –，1）作为催化剂，进行还原偶联明确定义的铁（II）/（EtO）3 SiH体系可实现硝基芳烃与烯烃的合成。通过分子间或分子内的还原偶联，已经在一锅中直接合成了各种支链胺和吲哚衍生物。机理研究表明，催化作用是由铁（II）催化剂与硅烷活化硝基芳烃而引发的，从而生成用于C-N键偶联的铁-亚硝基芳烃中间体。
• NHC-carbene cyclopentadienyl iron based catalyst for a general and efficient hydrosilylation of imines
  作者：Luis C. Misal Castro、Jean-Baptiste Sortais、Christophe Darcel

  DOI：10.1039/c1cc14403k

  日期：——

  A general and efficient hydrosilylation of imines catalysed by a well defined NHC-carbene cyclopentadienyl iron complex has been developed. Both aldimines and ketimines are converted to the corresponding amines under mild conditions, and under visible light activation.

  已经开发出一种通用且高效的由明确的NHC-卡宾环戊二烯基铁络合物催化的亚胺的水硅化反应。醛亚胺和酮亚胺在温和条件下以及可见光激活下转化为相应的胺。
• Amine Synthesis through Mild Catalytic Hydrosilylation of Imines using Polymethylhydroxysiloxane and [RuCl2(arene)]2 Catalysts
  作者：Bin Li、Jean-Baptiste Sortais、Christophe Darcel、Pierre H. Dixneuf

  DOI：10.1002/cssc.201100585

  日期：2012.2.13

  Tolerate silicone! The stable [RuCl2(p‐cymene]2 complex is an efficient catalyst for the direct chemoselective hydrosilylation of functionalized aldimines and ketimines into amines, using polymethylhydroxysiloxane as an inexpensive, stable, and safe hydrosilane source. The catalysis operates in ethanol, under air at room temperature, and tolerates the ketone ester and alkene functionality.

  耐硅胶！稳定的[RuCl 2（p- cymene）2络合物是一种有效的催化剂，可使用聚甲基羟基硅氧烷作为廉价，稳定且安全的氢化硅烷源，将官能化的亚胺和酮亚胺直接化学选择性氢化硅烷化为胺。在室温下，并能耐受酮酯和烯烃的官能团。
• A Highly Efficient Base-Metal Catalyst: Chemoselective Reduction of Imines to Amines Using An Abnormal-NHC–Fe(0) Complex
  作者：Mrinal Bhunia、Pradip Kumar Hota、Gonela Vijaykumar、Debashis Adhikari、Swadhin K. Mandal

  DOI：10.1021/acs.organomet.6b00478

  日期：2016.9.12

  A base-metal, Fe(0)-catalyzed hydrosilylation of imines to obtain amines is reported here which outperforms its noble-metal congeners with the highest TON of 17000. The catalyst, (aNHC)Fe(CO)(4), works under very mild conditions, with extremely low catalyst loading (down to 0.005 mol %), and exhibits excellent chemoselectivity. The facile nature of the imine reduction under mild conditions has been further demonstrated by reducing imines towards expensive commercial amines and biologically important N-alkylated sugars, which are difficult to achieve otherwise. A mechanistic pathway and the source of chemoselectivity for imine hydrosilylation have been proposed on the basis of the well-defined catalyst and isolable intermediates along the catalytic cycle.