(2-azido-(2S)-((1R,3S,4S)-4-azido-4-methyl-3-(phenylselenyl)cyclohexyl)propyl)(phenyl)selane

• 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: (2-azido-(2S)-((1R,3S,4S)-4-azido-4-methyl-3-(phenylselenyl)cyclohexyl)propyl)(phenyl)selane
• 英文别名: [(2S)-2-azido-2-[(1R,3S,4S)-4-azido-4-methyl-3-phenylselanylcyclohexyl]propyl]selanylbenzene
• 化学式: C₂₂H₂₆N₆Se₂
• 分子量: 532.409
• InChiKey: LPKFCADUJGPDIC-KDXIVRHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甜橙提取物 、 苯基硒基三氟甲烷磺酸酯 在 sodium azide 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 26.5h， 以41%的产率得到(2-azido-(2R)-((1R,3S,4S)-4-azido-4-methyl-3-(phenyselenyl)cyclohexyl)propyl)(phenyl)selane
  参考文献：
  名称：

  Synthesis of enantiomerically pure β-azidoselenides starting from natural terpenes

  摘要：

  Several unsaturated natural terpenes have been easily converted, in good yields, into the corresponding enantiomerically pure P-azidoselenides by addition of the electrophilic selenium reagent PhSeOTf in the presence of sodium azide. These reactions are stereospecific anti additions, which occur with a Markovnikov orientation. Examples of the synthetic importance of these beta-azidoselenides are also reported. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.047

文献信息

• Synthesis of enantiomerically pure β-azidoselenides starting from natural terpenes
  作者：Marcello Tiecco、Lorenzo Testaferri、Claudio Santi、Cristina Tomassini、Stefano Santoro、Francesca Marini、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tet.2007.09.047

  日期：2007.12

  Several unsaturated natural terpenes have been easily converted, in good yields, into the corresponding enantiomerically pure P-azidoselenides by addition of the electrophilic selenium reagent PhSeOTf in the presence of sodium azide. These reactions are stereospecific anti additions, which occur with a Markovnikov orientation. Examples of the synthetic importance of these beta-azidoselenides are also reported. (c) 2007 Elsevier Ltd. All rights reserved.