2-octyl-1-(p-tolyl)aziridine | 1349696-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-octyl-1-(p-tolyl)aziridine
• 英文别名: 2-Octyl-1-(p-tolyl)aziridine；1-(4-methylphenyl)-2-octylaziridine
• CAS: 1349696-80-5
• 化学式: C₁₇H₂₇N
• 分子量: 245.408
• InChiKey: MNXMSBHIZSVLAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  正癸烯 、 p-叠氮甲苯 在 [(^Me,EtTC^Ph)Fe(CH₃CN)₂](PF₆)₂ 作用下， 反应 18.17h， 以82.1%的产率得到2-octyl-1-(p-tolyl)aziridine
  参考文献：
  名称：

  用可重复使用的大环四卡宾铁催化剂从烯烃和芳基叠氮化物合成氮丙啶

  摘要：

  合成了一种以大环四碳烯配体为载体的新型铁氮杂催化剂。催化剂 [((Me,Et)TC(Ph))Fe(NCCH(3))(2)](PF(6))(2) 是由四咪唑鎓前体 ((Me,Et)TC( Ph))(I)(4) 并通过核磁共振光谱、电喷雾电离质谱和单晶 X 射线衍射表征。这种铁配合物在“C(2) + N(1)”加成反应中催化供电子芳基叠氮化物和各种取代的脂肪族烯烃（包括四取代的烯烃）的氮丙啶化。最后，催化剂可以回收并重复使用多达 3 次，而不会显着降低收率。

  DOI：

  10.1021/ja2090965

文献信息

• Synthesis of Aziridines from Alkenes and Aryl Azides with a Reusable Macrocyclic Tetracarbene Iron Catalyst
  作者：S. Alan Cramer、David M. Jenkins

  DOI：10.1021/ja2090965

  日期：2011.12.7

  synthesized from the tetraimidazolium precursor ((Me,Et)TC(Ph))(I)(4) and characterized by NMR spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction. This iron complex catalyzes the aziridination of electron-donating aryl azides and a wide variety of substituted aliphatic alkenes, including tetrasubstituted ones, in a "C(2) + N(1)" addition reaction. Finally,

  合成了一种以大环四碳烯配体为载体的新型铁氮杂催化剂。催化剂 [((Me,Et)TC(Ph))Fe(NCCH(3))(2)](PF(6))(2) 是由四咪唑鎓前体 ((Me,Et)TC( Ph))(I)(4) 并通过核磁共振光谱、电喷雾电离质谱和单晶 X 射线衍射表征。这种铁配合物在“C(2) + N(1)”加成反应中催化供电子芳基叠氮化物和各种取代的脂肪族烯烃（包括四取代的烯烃）的氮丙啶化。最后，催化剂可以回收并重复使用多达 3 次，而不会显着降低收率。
• Alkene Aziridination
  申请人：University of Tennessee Research Foundation

  公开号：US20130345431A1

  公开（公告）日：2013-12-26

  Disclosed are metal-bound tetracarbene catalysts, such as iron based aziridination catalyst, having the formula: wherein X is a group 6, 7, 8, 9, or 10 metal and wherein Z is a hydrogen, alkyl, aryl or organic group, wherein the alkyl, aryl or organic group is optionally are independently substituted. In a specific example, a metal-bound tetracarbene catalyst has the formula: Also disclosed are methods of making (synthesizing), transmetallation reagents, these agents, metal-bound tetracarbene catalysts, and a method of catalytic alkene aziridination, using the disclosed metal-bound tetracarbene catalysts.

  本文披露了金属配位的四齿卡宾催化剂，如基于铁的环氧乙烷化催化剂，其化学式如下：其中X是6、7、8、9或10族金属，Z是氢、烷基、芳基或有机基，其中烷基、芳基或有机基可以是独立取代的。在一个具体示例中，金属配位的四齿卡宾催化剂的化学式如下：还披露了制备（合成）转金属试剂、这些试剂、金属配位的四齿卡宾催化剂以及使用披露的金属配位的四齿卡宾催化剂进行催化烯烃环氧乙烷化的方法。
• Alkene aziridination
  申请人：University of Tennessee Research Foundation

  公开号：US09050589B2

  公开（公告）日：2015-06-09

  Disclosed are metal-bound tetracarbene catalysts, such as iron based aziridination catalyst, having the formula: wherein X is a group 6, 7, 8, 9, or 10 metal and wherein Z is a hydrogen, alkyl, aryl or organic group, wherein the alkyl, aryl or organic group is optionally are independently substituted. In a specific example, a metal-bound tetracarbene catalyst has the formula: Also disclosed are methods of making (synthesizing), transmetallation reagents, these agents, metal-bound tetracarbene catalysts, and a method of catalytic alkene aziridination, using the disclosed metal-bound tetracarbene catalysts.

  本发明涉及金属配位四卡宾催化剂，例如基于铁的环氧化胺催化剂，其化学式如下：其中X为第6、7、8、9或10族金属，Z为氢、烷基、芳基或有机基团，其中烷基、芳基或有机基团可以独立地被取代。在一个具体的例子中，金属配位四卡宾催化剂的化学式为：本发明还涉及制备（合成）转金属试剂、这些试剂、金属配位四卡宾催化剂的方法，以及使用所述金属配位四卡宾催化剂进行催化烯烃环氧化胺化的方法。
• Synthesis of Fully Aliphatic Aziridines with a Macrocyclic Tetracarbene Iron Catalyst
  作者：Preeti P. Chandrachud、Heather M. Bass、David M. Jenkins

  DOI：10.1021/acs.organomet.6b00066

  日期：2016.6.13

  A second-generation aziridination catalyst supported by a borate-based dianionic macrocyclic tetracarbene ligand has been synthesized. The new macrocyclic tetracarbene iron(II) complex catalyzed the aziridination of alkyl azides and aliphatic alkenes showcasing the first fully aliphatic version of this C-2 + N-1 reaction. High isolated yields were obtained when no functional groups were present on the organic azides and alkenes, while modest yields were achieved when nonprotic functional groups were included. Even multiple functional groups can be added to the azide and alkene fragments to produce the most complex aziridines yet synthesized by this C-2 + N-1 catalytic reaction. The catalyst generated higher yields for aziridination with aryl azides and alkenes than the previously reported catalyst, [((TCPh)-T-Me,Et)Fe(NCCH3)(2)](PF6)(2). The contrast is particularly apparent with functionalized aryl azides where the second-generation catalyst now provides practical yields for synthetic chemistry. Finally, catalytic intramolecular aziridination was investigated since many natural products with aziridines feature bicyclic tertiary aziridines. For five- and six-membered rings, the bicyclic aziridines were formed catalytically, in contrast to previously studied catalyzed and uncatalyzed reactions.
• Catalytic aziridination with alcoholic substrates <i>via</i> a chromium tetracarbene catalyst
  作者：C. Luke Keller、Jesse L. Kern、Bradley D. Terry、Sharani Roy、David M. Jenkins

  DOI：10.1039/c7cc08928g

  日期：——

  The first examples of aziridination catalysis with a chromium complex are communicated. This tetracarbene chromium complex provides novel catalytic aziridination reactions with protic substrates such as alcohols or amines on the alkene or organic azide and is the most effective catalyst at low alkene loading for aliphatic alkenes to date.

  交流了用铬配合物进行叠氮化催化的第一个例子。这种四碳烯铬络合物可与质子性底物（例如烯烃或有机叠氮化物上的醇或胺）提供新颖的催化叠氮化反应，并且是迄今为止低烯烃装载量下最有效的脂肪族烯烃催化剂。