4-aziadamantan-1-amine | 407625-93-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-aziadamantan-1-amine
• 英文别名: Spiro[adamantane-2,2'-diazirine]-7-amine；spiro[adamantane-4,3'-diazirine]-1-amine
• CAS: 407625-93-8
• 化学式: C₁₀H₁₅N₃
• 分子量: 177.249
• InChiKey: ABOVVTNKZNPPSM-UHFFFAOYSA-N

物化性质

• 沸点：
  272.1±50.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.74
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-aziadamantan-1-amine 反应 2.0h， 生成 bis(5-aminoadamantan-2-ylidene)hydrazine
  参考文献：
  名称：

  γ-取代的金刚烷内酯的分子内和分子间反应选择性

  摘要：

  进行了具有γ-取代基（R）的金刚烷亚烃类的研究，以评估位于远端的官能团的诱导和空间效应如何影响分子内和分子间产物的选择性。3 H-二嗪嗪被热解或光解以生成相应的卡宾。在快速加热下，通过分子内的1,3-CH插入将生成的碳烯异构化为2,4-二氢加金刚烷。当R是电子供体（R D）时，大多数会生成不对称的1取代衍生物，但是当R是电子受体（R A时））形成对称的7位取代基。当溶液暴露于UV-A光线下时，由羧甲基和溶剂形成的分子间加合物以较少量的分子内产物为主。3 H-重氮基的价异构化也提供了重氮化合物。在甲醇中，重氮化合物的质子化作用产生相应的2-金刚烷基阳离子时，其偶联作用超过了。富马腈通过捕集重氮化合物来控制这种转移。该加合物具有大多抗与R = R构型d和顺式，其中R = R安排甲。之间的连接如和-抗-产物的形成，并且的小号-与顺式-products被认为是两个截然不同的卡宾构象之间的快速平衡的

  DOI：

  10.1021/jo202132c
• 作为产物：
  描述：

  2-oxaadamantan-5-amine 在 氨 、 hydroxylamine-O-sulfonic acid 、 chromium(VI) oxide 、 硫酸 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 6.33h， 生成 4-aziadamantan-1-amine
  参考文献：
  名称：

  2H-Azirines from a Concerted Addition of Alkylcarbenes to Nitrile Groups

  摘要：

  Photolysis of aziadamantanos in the presence of fumoronitrile (FN) unexpectedly afforded conjugated 2H-azirines resulting from addition of the carbene to the CN triple bond. This represents the first example of a direct azirine formation starting from an alkylcarbene for which a concerted pathway is postulated. The novel outcome if the reaction is favored by the prior formation of a carbene-alkene complex, a type of adduct that only recently has been described.

  DOI：

  10.1021/ol100703r

文献信息

• Reversal of Diastereoselectivities in Intra- and Intermolecular Reactions of 2-Adamantanylidenes Primarily Caused by Electron-Donating and Electron- Withdrawing Substituents on C5
  作者：Wolfgang Knoll、Michael M. Bobek、Hermann Kalchhauser、Murray G. Rosenberg、Udo H. Brinker

  DOI：10.1021/ol0350700

  日期：2003.8.1

  A reversal of diastereoselectivity was observed for novel 5-(trimethylsilyl)adamantan-2-ylidene (1c) with regard to 5-hydroxyadamantan-2-ylidene (1a). Ostensibly in intermolecular reactions, 5-substituted 2-adamantanylidenes (1) are sterically unbiased. However, inductive effects originating from the pendant group bend the divalent carbon bridge of 1 either toward (ERG's, e.g., -Si(CH3)(3)) or away from (EWG's, e.g., -OH) the gamma-position. Hence, the more exposed side is more susceptible to intermolecular reaction and the other side concomitantly undergoes intramolecular 1,3-CH insertions more readily.
• 4-Aziadamantan-1-amine: synthesis, reactions and cyclodextrin complexes
  作者：Wolfgang Knoll、Michael M Bobek、Gerald Giester、Udo H Brinker

  DOI：10.1016/s0040-4039(01)02013-5

  日期：2001.12

  A new and potentially therapeutic diazirine, 4-aziadamantan-1-amine, was synthesized. Structural characterization also included single crystal X-ray diffraction analysis. Photolysis of the title Compound in the solid phase afforded an azine. In contrast. pyrolysis in the gas phase gave two intramolecular carbene insertion products in a 4:1 ratio. A rationale for the observed diastereoselectivity is offered based upon ab initio calculations. Finally, inclusion compounds of the title compound with alpha- and beta -cyclodextrin were prepared. A 2:1 complex bearing two hosts was formed with alpha -cyclodextrin and a 1:1 complex was obtained with beta -cyclodextrin. The association constants were determined via induced circular dichroism (ICD) analysis. (C), 2001 Elsevier Science Ltd. All rights reserved.