adamantan-1-yl-phenyl-amine | 52917-67-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: adamantan-1-yl-phenyl-amine
• 英文别名: N-(2-adamantyl)aniline；Adamant-2-ylphenylamin；N-(2-Adamantyl)-anilin；N-2-Adamantylanilin；Aniline, N-(2-adamantyl)-；N-phenyladamantan-2-amine
• CAS: 52917-67-6
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: ZEFPCBGROANPME-UHFFFAOYSA-N

物化性质

• 沸点：
  362.9±11.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  adamantan-1-yl-phenyl-amine 、 六氟丙酮 以 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 反应 24.0h， 以64%的产率得到N-(2-adamantyl)-4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)aniline
  参考文献：
  名称：

  C-hydroxyalkylation of N-adamantylanilines by hexafluoroacetone and methyl trifluoropyruvate

  摘要：

  DOI：

  10.1007/bf00962133
• 作为产物：
  描述：

  2-金刚烷醇 、 苯胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 3.0h， 以95%的产率得到adamantan-1-yl-phenyl-amine
  参考文献：
  名称：

  N-Alkylation of amines through hydrogen borrowing over a heterogeneous Cu catalyst

  摘要：

  烷基卤代物在合成胺方面的替代，是合成化学家关注的重点。通过采用多相铜催化剂，可在一次反应中从二级醇、苄醇以及苯胺一步合成二级胺，且整个过程无需添加额外物质，本质上安全，且不会产生废物。

  DOI：

  10.1039/c3ra44364g

文献信息

• Studies on Pd/imidazolium salt protocols for aminations of aryl bromides and iodides using lithium hexamethyldisilazide (LHMDS)
  作者：Israel Conesa Lerma、Mark J. Cawley、F. Geoffrey N. Cloke、Katherine Arentsen、James S. Scott、Stuart E. Pearson、John Hayler、Stephen Caddick

  DOI：10.1016/j.jorganchem.2005.07.084

  日期：2005.12

  The reactions of a range of secondary amines with aryl bromides and iodides have been performed using an in situ protocol involving palladium and imidazolium salts. Many of these reactions proceed at room temperature, providing a mild protocol for aminations of aryl iodides and bromides. Key to the success of this procedure is the use of lithium hexamethyldisilazide (LHMDS) as base.

  一系列仲胺与芳基溴化物和碘化物的反应已使用涉及钯盐和咪唑盐的原位方案进行。这些反应中的许多反应都是在室温下进行的，为芳基碘化物和溴化物的胺化提供了温和的方案。该方法成功的关键是使用六甲基二硅叠氮化锂（LHMDS）作为碱。
• Host–guest assembly of adamantyl tethered squaraine in β-cyclodextrin for monitoring pH in living cells
  作者：Wenjian Xu、Xiaochan Zhu、Guimei Wang、Chuanguo Sun、Qingfeng Zheng、Huanghao Yang、Nanyan Fu

  DOI：10.1039/c4ra08506j

  日期：——

  A host-guest assembly of adamantyl tethered squaraine in β-cyclodextrin has been designed as a sensitive near-infrared fluorescent probe for imaging intracellular pH in living cells.

  一个由脒基化的苯并二氮蒽与β-环糊精组成的宿主-客体组装体被设计为一种敏感的近红外荧光探针，用于成像活细胞内的pH值。
• Aromatic ring polymer and low-dielectric material
  申请人：Ueda Mitsuru

  公开号：US20060178542A1

  公开（公告）日：2006-08-10

  An aromatic ring polymer wherein adjacent aromatic ring skeletons cannot have a conformation positioned on a single plane due to mutual steric hindrance of the adjacent aromatic ring skeletons and is represented by the following formula (1): X-A-Y-B n (1) wherein X and Y may be the same or different, and each represent a monocyclic or heterocyclic bivalent aromatic group which may be substituted with R; A and B may be the same or different, and are each a single bond or a substituent which can contain an aromatic group; and n is an integer of 5 to 1000000. This polymer has a low dielectric constant, and is excellent in heat resistance and strength.

  这是一种芳香环聚合物，其中相邻的芳香环骨架由于相互的立体位阻而不能具有单一平面构象，其化学式表示为(1)：X-A-Y-Bn(1)，其中X和Y可以相同或不同，分别代表可以被R取代的单环或杂环二价芳香基团；A和B可以相同或不同，分别为单键或含有芳香基团的取代基；n为5到1000000的整数。这种聚合物具有低介电常数，具有良好的耐热性和强度。
• Arylation of adamantanamines: IX. Copper(I)-catalyzed arylation of adamantane-containing amines
  作者：A. D. Averin、S. P. Panchenko、A. S. Abel、O. A. Maloshitskaya、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428017120028

  日期：2017.12

  Copper(I)-catalyzed arylation of 14 adamantane-containing amines with iodobenzene, 1-fluoro-4-iodobenzene, 1-iodo-4-(trifluoromethyl) benzene, and 1-iodo-4-methoxybenzene has been studied under the conditions optimized previously. The yields of the N-arylation products have been shown to depend in a complicated manner on the amine structure, steric environment of the amino group, and substituent nature in iodobenzene.
• Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes
  作者：A. D. Averin、M. A. Ulanovskaya、V. V. Kovalev、A. K. Buryak、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428010010069

  日期：2010.1

  Palladium-catalyzed amination of isomeric bromochloro- and dibromobenzenes with 1- and 2-aminoadamantanes was studied. The best yields of the corresponding monoamination products were obtained in the reactions of 2-aminoadamantane with bromochlorobenzenes. The arylation of 1-aminoadamantane was successful in the presence of donor phosphine ligand. The amination of o- and m-dibromobenzenes was strongly complicated by formation of diamination products. Conditions ensuring predominant formation of the latter were found. The arylation of 2-aminoadamantane was accompanied by oxidation of the initial amine and reduction of aryl halide.