1-(o-azidophenyl)ethylamine | 146954-07-6

• 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: 1-(o-azidophenyl)ethylamine
• 英文别名: 1-(2-Azidophenyl)ethanamine
• CAS: 146954-07-6
• 化学式: C₈H₁₀N₄
• 分子量: 162.194
• InChiKey: VIFNPVCIUMGSJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(o-azidophenyl)ethylamine 在 三甲基膦 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 trans-2,8-dimethyl-1,1,2-triphenyl-1,2-dihydroazeto[2,-b]quinazoline
  参考文献：
  名称：

  New Stereoselective Intramolecular [2 + 2] Cycloadditions between Ketenimines and Imines on an ortho-Benzylic Scaffold:  1,4-Asymmetric Induction

  摘要：

  Efficient 1,4-asymmetric induction has been achieved in the highly stereocontrolled intramolecular [2 + 2] cycloadditions between ketenimines and imines, leading to 1,2-dihydroazeto[2,1-b]-quinazolines. The chiral methine carbon adjacent to the iminic nitrogen controls the exclusive formation of the cycloadducts with relative trans configuration at C2 and C8. The stepwise mechanistic model, based on theoretical calculations, fully supports the stereochemical outcome of these cycloadditions.

  DOI：

  10.1021/jo0055178
• 作为产物：
  描述：

  2-叠氮基苯甲醛 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 51.0h， 生成 1-(o-azidophenyl)ethylamine
  参考文献：
  名称：

  Synthetic applications of bis(iminophosphoranes). One-pot preparation of rigid bicyclic guanidines

  摘要：

  A one-pot synthesis of [6 + 6], [6 + 7], and [6 + 8] bicyclic guanidines based on a new method of dihydropyrimido annelation, which involves reaction of bis(iminophosphoranes) with aryl isocyanates or isothiocyanates is described. The method is also applicable for the preparation of chiral bicyclic guanidines.

  DOI：

  10.1021/jo00059a015

文献信息

• Highly Efficient Induction of Chirality in Intramolecular [2 + 2] Cycloadditions between Ketenimines and Imines
  作者：Fernando P. Cossío、Ana Arrieta、Begoña Lecea、Mateo Alajarín、Angel Vidal、Fulgencio Tovar

  DOI：10.1021/jo991826q

  日期：2000.6.1

  Highly stereocontrolled, intramolecular [2 + 2] cycloadditions between ketenimines and imines leading to 1,2-dihydroazeto[2, 1-b]quinazolines have been achieved. The source of stereocontrol is a chiral carbon atom adjacent either to the iminic carbon or nitrogen atom. In the first case, the stereocontrol stems from the preference for the axial conformer in the first transition structure. In the second

  酮亚胺和亚胺之间高度立体控制的分子内[2 + 2]环加成反应导致了1,2-二氢氮杂并[2，1-b]喹唑啉的形成。立体控制的来源是与亚氨基碳原子或氮原子相邻的手性碳原子。在第一种情况下，立体声控制源于在第一过渡结构中偏爱轴向适形器。在第二种情况下，立体控制的起源在于所形成的CC键与对应于极性CX键的sigma轨道之间的双电子稳定相互作用，X为负电原子。这些模型可以扩展到其他相关系统，以预测此分子内反应中的立体化学结果。
• Tripod-Tripod Coupling of Triazides with Triphosphanes. The Synthesis, Characterization, and Stability in Solution of New Cage Compounds: Chiral Macrobicyclic Triphosphazides
  作者：Mateo Alajarín、Antonia López-Lázaro、Angel Vidal、José Berná

  DOI：10.1002/(sici)1521-3765(19981204)4:12<2558::aid-chem2558>3.0.co;2-3

  日期：1998.12.4
• Synthetic applications of bis(iminophosphoranes). One-pot preparation of rigid bicyclic guanidines
  作者：Pedro Molina、Mateo Alajarin、Angel Vidal

  DOI：10.1021/jo00059a015

  日期：1993.3

  A one-pot synthesis of [6 + 6], [6 + 7], and [6 + 8] bicyclic guanidines based on a new method of dihydropyrimido annelation, which involves reaction of bis(iminophosphoranes) with aryl isocyanates or isothiocyanates is described. The method is also applicable for the preparation of chiral bicyclic guanidines.
• New Stereoselective Intramolecular [2 + 2] Cycloadditions between Ketenimines and Imines on an <i>o</i><i>rtho</i>-Benzylic Scaffold:  1,4-Asymmetric Induction
  作者：Mateo Alajarín、Angel Vidal、Fulgencio Tovar、M. Carmen Ramírez de Arellano、Fernando P. Cossío、Ana Arrieta、Begoña Lecea

  DOI：10.1021/jo0055178

  日期：2000.11.1

  Efficient 1,4-asymmetric induction has been achieved in the highly stereocontrolled intramolecular [2 + 2] cycloadditions between ketenimines and imines, leading to 1,2-dihydroazeto[2,1-b]-quinazolines. The chiral methine carbon adjacent to the iminic nitrogen controls the exclusive formation of the cycloadducts with relative trans configuration at C2 and C8. The stepwise mechanistic model, based on theoretical calculations, fully supports the stereochemical outcome of these cycloadditions.