(+/-)-trans-1-azido-2-iodocyclopentane

• 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: (+/-)-trans-1-azido-2-iodocyclopentane
• 化学式: C₅H₈IN₃
• 分子量: 237.043
• InChiKey: RTXNGBGMOOCHAT-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.76
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-1-azido-2-iodocyclopentane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以80%的产率得到环戊烯亚胺
  参考文献：
  名称：

  Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes

  摘要：

  The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3-methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction.

  DOI：

  10.1080/10426501003773787
• 作为产物：
  描述：

  环戊烯 在 sodium azide 、 一氯化碘 作用下， 以 乙腈 为溶剂， 生成 (+/-)-trans-1-azido-2-iodocyclopentane
  参考文献：
  名称：

  离散钇配合物催化TMSN3或TMMSCN介导的氮杂氮丙啶的对映选择性脱对称

  摘要：

  是这样吗 钇-salen二聚体（见结构； N蓝色，O红色，Y品红色）通过TMSCN和TMSN 3催化内消旋氮丙啶的高度对映选择性开环。为了解释单聚体催化剂和二聚体催化剂之间选择性的巨大差异，提出了一种基于二聚体固态结构的双金属机理。

  DOI：

  10.1002/anie.200804415

文献信息

• Enantioselective Desymmetrization of<i>meso</i>-Aziridines with TMSN₃or TMSCN Catalyzed by Discrete Yttrium Complexes
  作者：Bin Wu、Judith C. Gallucci、Jon R. Parquette、T. V. RajanBabu

  DOI：10.1002/anie.200804415

  日期：2009.1.26

  Y is it so? Dimeric yttrium–salen complexes (see structure; N blue, O red, Y magenta) catalyze the highly enantioselective ring‐opening of meso‐aziridines by TMSCN and TMSN3. To explain the dramatic differences in the selectivity between mono‐ and dimeric catalysts, a dimetallic mechanism based on the solid‐state structure of the dimer is proposed.

  是这样吗 钇-salen二聚体（见结构； N蓝色，O红色，Y品红色）通过TMSCN和TMSN 3催化内消旋氮丙啶的高度对映选择性开环。为了解释单聚体催化剂和二聚体催化剂之间选择性的巨大差异，提出了一种基于二聚体固态结构的双金属机理。
• A general synthesis of 2h-azirines from olefins. Fused azirines.
  作者：Alfred Hassner、Frank W. Fowler

  DOI：10.1016/s0040-4039(00)90998-5

  日期：1967.1
• Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes
  作者：Mariam Namutebi、Eoghan M. McGarrigle、Varinder K. Aggarwal

  DOI：10.1080/10426501003773787

  日期：2010.5.27

  The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3-methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction.