(S)-4-azidohept-1-ene | 850538-42-0

• 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: (S)-4-azidohept-1-ene
• 英文别名: (4S)-4-azidohept-1-ene
• CAS: 850538-42-0
• 化学式: C₇H₁₃N₃
• 分子量: 139.2
• InChiKey: DVNZIMCCXHIKRZ-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (S)-4-azidohept-1-ene 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 99.0h， 生成 N-(R)-cyclohex-2-enyl-2-nitro-N-((S)-1-propylbut-3-enyl)benzenesulfonamide
  参考文献：
  名称：

  Total Synthesis of (+)-trans-195A

  摘要：

  The first enantioselective synthesis of (+)-trans-195A is described. The structure has been constructed by ring-rearrangement metathesis (RRM) and zirconium-mediated Negishi-coupling, used for the first time to prepare 6,6-membered heterocycles, as key steps. By comparison of the synthesized material with the isolated natural product, the absolute configuration of natural trans-195A was determined to be (2R,4aS,5R,8aS)-(-).

  DOI：

  10.1021/ol0474610
• 作为产物：
  描述：

  (4R)-hept-1-en-ol 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 (S)-4-azidohept-1-ene
  参考文献：
  名称：

  Total Synthesis of (+)-trans-195A

  摘要：

  The first enantioselective synthesis of (+)-trans-195A is described. The structure has been constructed by ring-rearrangement metathesis (RRM) and zirconium-mediated Negishi-coupling, used for the first time to prepare 6,6-membered heterocycles, as key steps. By comparison of the synthesized material with the isolated natural product, the absolute configuration of natural trans-195A was determined to be (2R,4aS,5R,8aS)-(-).

  DOI：

  10.1021/ol0474610

文献信息

• Total Synthesis of (+)-<i>trans</i>-<b>195A</b>
  作者：Nicole Holub、Jürgen Neidhöfer、Siegfried Blechert

  DOI：10.1021/ol0474610

  日期：2005.3.1

  The first enantioselective synthesis of (+)-trans-195A is described. The structure has been constructed by ring-rearrangement metathesis (RRM) and zirconium-mediated Negishi-coupling, used for the first time to prepare 6,6-membered heterocycles, as key steps. By comparison of the synthesized material with the isolated natural product, the absolute configuration of natural trans-195A was determined to be (2R,4aS,5R,8aS)-(-).