1,2-Bis(2-azidophenyl)ethane | 82230-83-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-Bis(2-azidophenyl)ethane
• 英文别名: o-Azidodiphenylaethan；1-Azido-2-[2-(2-azidophenyl)ethyl]benzene
• CAS: 82230-83-9
• 化学式: C₁₄H₁₂N₆
• 分子量: 264.289
• InChiKey: ZGZZHKKDLGMUMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-Bis(2-azidophenyl)ethane 在 4-二甲氨基吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 5,6,18,19-tetradehydro-5,12,13,18,25,26-hexahydrotetrabenzo<1,3,10,12>tetraazacyclooctadecine
  参考文献：
  名称：

  A New and Efficient Preparation of Cyclic Carbodiimides from Bis(iminophosphoranes) and the System Boc2O/DMAP

  摘要：

  A one-pot synthesis of cyclic carbodiimides which involves reaction of C,C-bis(aryliminophosphoranes) connected by aliphatic bridges with Boc(2)O in the presence of DMAP is described. The method is also applicable when a heteroatom such as oxygen or nitrogen is incorporated into the tether connecting the two aromatic rings. A conformation study has been carried out on carbodiimide 23a, which posseses a central nine-membered ring, using H-1 NMR spectroscopy and semiempirical as well as molecular mechanics calculations.

  DOI：

  10.1021/jo00103a022
• 作为产物：
  描述：

  2,2-亚乙基二苯胺 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 15.0h， 生成 1,2-Bis(2-azidophenyl)ethane
  参考文献：
  名称：

  Synthesis of Phosphaguanidines by Hydrophosphination of Carbodiimides with Phosphine Boranes

  摘要：

  The direct addition of anionic secondary phosphine boranes to carbodiimides yields both chiral and achiral phosphaguanidine boranes, under ambient temperature conditions. An analogous preparation of menthol-derived phosphinite boranes is also described. These products can be deborinated to give the corresponding phosphines, and subsequently oxidized to give phosphine oxides. The robustness of this method was further demonstrated in the synthesis of structurally novel cyclic phosphaguanidines.

  DOI：

  10.1021/jo501841s

文献信息

• An efficient preparation of macrocycles containing two tetra-coordinate phosphorus atoms
  作者：P. Molina、M. Alajarín、A. Arques、P. Sánchez-Andrada、A. Vidal、M.V. Vinader

  DOI：10.1016/s0022-328x(96)06494-7

  日期：1997.2

  The Staudinger reaction between bis(azides) and bis(phosphines) under mild conditions provides macrocyclic bis(iminophosphoranes) (at least 12-membered rings) in excellent to moderate yield. The method also allows the incorporation of a heteroatom into the chain connecting the two aromatic or heteroaromatic rings.
• US6270939B1
  申请人：——

  公开号：US6270939B1

  公开（公告）日：2001-08-07
• Synthesis of Phosphaguanidines by Hydrophosphination of Carbodiimides with Phosphine Boranes
  作者：Carl A. Busacca、John A. Milligan、Eakkaphon Rattanangkool、Cyrus Ramavarapu、Anji Chen、Anjan K. Saha、Zhibin Li、Heewon Lee、Steven J. Geib、Guijun Wang、Chris H. Senanayake、Peter Wipf

  DOI：10.1021/jo501841s

  日期：2014.10.17

  The direct addition of anionic secondary phosphine boranes to carbodiimides yields both chiral and achiral phosphaguanidine boranes, under ambient temperature conditions. An analogous preparation of menthol-derived phosphinite boranes is also described. These products can be deborinated to give the corresponding phosphines, and subsequently oxidized to give phosphine oxides. The robustness of this method was further demonstrated in the synthesis of structurally novel cyclic phosphaguanidines.
• A New and Efficient Preparation of Cyclic Carbodiimides from Bis(iminophosphoranes) and the System Boc2O/DMAP
  作者：Pedro Molina、Mateo Alajarin、Pilar Sanchez-Andrada、Jose Elguero、Maria Luisa Jimeno

  DOI：10.1021/jo00103a022

  日期：1994.12

  A one-pot synthesis of cyclic carbodiimides which involves reaction of C,C-bis(aryliminophosphoranes) connected by aliphatic bridges with Boc(2)O in the presence of DMAP is described. The method is also applicable when a heteroatom such as oxygen or nitrogen is incorporated into the tether connecting the two aromatic rings. A conformation study has been carried out on carbodiimide 23a, which posseses a central nine-membered ring, using H-1 NMR spectroscopy and semiempirical as well as molecular mechanics calculations.