N-(3,5-bis(trifluoromethyl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine | 1262055-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-(3,5-bis(trifluoromethyl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine
• 英文别名: N-[3,5-bis(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-amine
• CAS: 1262055-69-5
• 化学式: C₁₈H₁₅F₆N
• 分子量: 359.314
• InChiKey: ZQIHEAJAQNBRNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2,3,4-四氢萘 、 以66 %的产率得到N-(3,5-bis(trifluoromethyl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine
  参考文献：
  名称：

  钌(V)末端芳基酰亚胺咔咯：分离、光谱表征和反应性

  摘要：

  末端 Ru( V )-亚氨基物种被认为与它们的 Ru( V )-氧代同系物一样对基团转移反应具有反应性，但研究较少。具有富电子的咔咯配体，相对稳定且可分离的Ru( V )–芳基酰亚胺配合物[Ru( tBu –Cor)(NAr)](H 3 ( tBu –Cor)=5,15-二苯基-10-(对叔丁基苯基)咔咯，Ar = 2,4,6-Me 3 C 6 H 2 (Mes)，2,6-(Pr) 2 C 6 H 3 (Dipp)，2,4,6-(Pr) ) 3 C 6 H 2 (Tipp)和3,5-(CF 3 ) 2 C 6 H 3 (BTF))可以在强还原条件下由[Ru( t Bu–Cor)] 2制备。通过高分辨率 ESI 质谱、X 波段 EPR、共振拉曼光谱、磁化率、元素分析以及计算研究对这种类型的S = ½ 的 Ru( V )-单芳基酰亚胺咔咯络合物进行了表征。 在加热/光照射（氙灯）条件下，配合物

  DOI：

  10.1039/d3sc02266h

文献信息

• Iron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides
  作者：Yi-Dan Du、Cong-Ying Zhou、Wai-Pong To、Hai-Xu Wang、Chi-Ming Che

  DOI：10.1039/d0sc00784f

  日期：——

  strategy for the design of C–N bond formation reactions under mild reaction conditions, the challenge being lack of selectivity as a free nitrene reactive intermediate is usually involved. Herein is described an iron(III) porphyrin catalysed sp3 C–H amination and alkene aziridination with selectivity by using organic azides as the nitrogen source under blue LED light (469 nm) irradiation. The photochemical

  在温和的反应条件下，可见光驱动的有机叠氮化物的氮烯转移和插入反应是设计C–N键形成反应的一种有吸引力的策略，因为通常涉及游离的腈反应性中间体，因此缺乏选择性的挑战。本文描述了铁（III）卟啉催化的sp 3通过使用有机叠氮化物作为氮源，在蓝色LED光（469 nm）照射下，进行C–H胺化和烯烃的叠氮化。光化学反应显示化学选择性和区域选择性，并且对于复杂的天然和生物活性化合物的后期功能化有效。机理研究表明，卟啉铁既起光敏剂的作用，又起催化剂的作用，产生了反应性的铁-氮化物中间体，随后形成C-N键。
• Ruthenium porphyrins-catalyzed atom-efficient amination of <font>C-H</font> bonds by arylazides
  作者：Daniela Intrieri、Alessandro Caselli、Fabio Ragaini、Sergio Cenini、Emma Gallo

  DOI：10.1142/s1088424610002501

  日期：2010.8

  Benzylic amines are synthesized in yield up to 90% by the Ru(TPP)CO -catalyzed amination of both exocyclic and endocyclic benzylic C-H bonds. The choice of arylazides as nitrogen sources confers to the methodology a good sustainability due to the formation of molecular nitrogen as the only stoichiometric by-product. A preliminary mechanistic investigation evidenced a critical role of the hydrocarbon concentration to drive the chemoselectivity of the reaction.

  通过 Ru(TPP)CO 催化外环和内环苄基 C-H 键的胺化反应，可合成出产率高达 90% 的苄胺。由于分子氮是唯一的化学副产物，选择芳基叠氮化物作为氮源使该方法具有良好的可持续性。初步的机理研究表明，碳氢化合物浓度对反应的化学选择性起着关键作用。
• Glycoporphyrin Catalysts for Efficient C–H Bond Aminations by Organic Azides
  作者：Giorgio Tseberlidis、Paolo Zardi、Alessandro Caselli、Damiano Cancogni、Matteo Fusari、Luigi Lay、Emma Gallo

  DOI：10.1021/acs.organomet.5b00436

  日期：2015.8.10

  We report herein the synthesis of new glycoporphyrin ligands which bear a glucopyranoside derivative on each meso-aryl moiety of the porphyrin skeleton. The saccharide unit is directly conjugated to the porphyrin or a triazole spacer is placed between the carbohydrate and porphyrin ring. The obtained glycoporphyrin ligands were employed to synthesize cobalt(II), ruthenium(II), and iron(III) complexes which were tested as catalysts of C-H bond aminations by organic azides. Two of the synthesized complexes were very efficient in promoting catalytic reactions, and the results achieved indicated that ruthenium and iron complexes show an interesting complementary catalytic activity in several amination reactions. The eco-friendly iron catalyst displayed very good chemical stability in catalyzing the amination reaction for three consecutive runs without losing catalytic activity.
• Co(porphyrin)-catalysed amination of 1,2-dihydronaphthalene derivatives by aryl azides
  作者：Paolo Zardi、Daniela Intrieri、Alessandro Caselli、Emma Gallo

  DOI：10.1016/j.jorganchem.2012.07.013

  日期：2012.10

  Co(porphyrin) complexes promote an unusual reactivity of dihydronaphthalene towards several aryl azides. The reaction affords the benzylic amine of tetrahydronaphthalene instead yielding the amine of dihydronaphthalene as it normally happens in the presence of Ru(porphyrin)CO catalysts. The amination process occurs with the concomitant reduction of the dihydronaphthalene double bond probably due to the high reactivity of the endocyclic C=C bond coupled with the good hydrogen donor capability of dihydronaphthalene. Two mechanisms for this reaction are proposed. (C) 2012 Elsevier B. V. All rights reserved.