(3Z)-8-azido-3-octene | 91106-52-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (3Z)-8-azido-3-octene
• 英文别名: (Z)-8-azidooct-3-ene
• CAS: 91106-52-4
• 化学式: C₈H₁₅N₃
• 分子量: 153.227
• InChiKey: KQTLPHAEFSWYQK-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3Z)-8-azido-3-octene 在 水 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 4-[(2S,3R)-3-ethyloxiran-2-yl]butan-1-amine
  参考文献：
  名称：

  A stereospecific synthesis of (±) α-conhydrine and (±) β-conhydrine.

  摘要：

  DOI：

  10.1016/s0040-4039(01)90008-5
• 作为产物：
  描述：

  (Z)-8-chlorooct-3-ene 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以96%的产率得到(3Z)-8-azido-3-octene
  参考文献：
  名称：

  A stereospecific synthesis of (±) α-conhydrine and (±) β-conhydrine.

  摘要：

  DOI：

  10.1016/s0040-4039(01)90008-5

文献信息

• A Triazolium‐Anchored Self‐Immolative Linker Enables Self‐Assembly‐Driven siRNA Binding and Esterase‐Induced Release
  作者：Selina Hollstein、Lamiaa M. A. Ali、Maëva Coste、Julian Vogel、Nadir Bettache、Sébastien Ulrich、Max von Delius

  DOI：10.1002/chem.202203311

  日期：2023.2.7

  AbstractThe increased importance of RNA‐based therapeutics comes with a need to develop next‐generation stimuli‐responsive systems capable of binding, transporting and releasing RNA oligomers. In this work, we describe triazolium‐based amphiphiles capable of siRNA binding and enzyme‐responsive release of the nucleic acid payload. In aqueous medium, the amphiphile self‐assembles into nanocarriers that can disintegrate upon the addition of esterase. Key to the molecular design is a self‐immolative linker that is anchored to the triazolium moiety and acts as a positively‐charged polar head group. We demonstrate that addition of esterase leads to a degradation cascade of the linker, leaving the neutral triazole compound unable to form complexes and therefore releasing the negatively‐charged siRNA. The reported molecular design and overall approach may have broad utility beyond this proof‐of‐principle study, because the underlying CuAAC “click” chemistry allows bringing together three groups very efficiently as well as cleaving off one of the three groups under the mild action of an esterase enzyme.
• A stereospecific synthesis of (±) α-conhydrine and (±) β-conhydrine.
  作者：Serge Pilard、Michel Vaultier

  DOI：10.1016/s0040-4039(01)90008-5

  日期：1984.1