(S)-(-)-1-(o-azidophenyl)ethylamine | 146987-06-6

• 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: (S)-(-)-1-(o-azidophenyl)ethylamine
• 英文别名: (S)-1-(2-azidophenyl)-ethylamine；(1S)-1-(2-azidophenyl)ethanamine
• CAS: 146987-06-6
• 化学式: C₈H₁₀N₄
• 分子量: 162.194
• InChiKey: VIFNPVCIUMGSJC-LURJTMIESA-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：

  (S)-(-)-1-(o-azidophenyl)ethylamine 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 25.5h， 生成 (1S)-N-[[3-methyl-1-phenyl-5-[(triphenyl-lambda5-phosphanylidene)amino]pyrazol-4-yl]methyl]-1-[2-[(triphenyl-lambda5-phosphanylidene)amino]phenyl]ethanamine
  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
• 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 (S)-(-)-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

• Stereocontrolled synthesis of azeto[2,1-b] quinazolines bearing three stereocenters via the intramolecular [2+2] cycloaddition between ketenimines and imines
  作者：Mateo Alajarı́n、Angel Vidal、Fulgencio Tovar、M.Carmen Ramı́rez de Arellano

  DOI：10.1016/j.tetasy.2003.11.025

  日期：2004.2

  A highly stereoselective synthesis of azeto[2,1-b]quinazolines bearing three stereocenters (C1, C2, and C8) has been achieved via intramolecular [2+2] cycloaddition between ketenimine and imine functions supported on an ortho-benzylic scaffold. An asymmetric center adjacent to the iminic nitrogen atom, the future C8 carbon of the bicyclic product, efficiently controls the absolute configuration of

  azeto [2,1的高度立体选择性合成b ]喹唑啉轴承3个立体中心（C1，C2，和C8）已经经由支撑在烯酮亚胺和亚胺函数之间的分子内[2 + 2]环加成而完成邻-benzylic支架。与亚氨基氮原子相邻的不对称中心，即双环产物的未来C8碳，有效地控制了氮杂环丁烷环的两个新的立体碳原子C1和C2的绝对构型。
• 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.