(2R*,5S*)-2-(cyano-methyl)-5-(iodomethyl)tetrahydrofuran | 123622-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R*,5S*)-2-(cyano-methyl)-5-(iodomethyl)tetrahydrofuran
• 英文别名: cis-2-(Cyanomethyl)-5-(iodomethyl)tetrahydrofuran；2-[(2S,5R)-5-(iodomethyl)oxolan-2-yl]acetonitrile
• CAS: 123622-66-2
• 化学式: C₇H₁₀INO
• 分子量: 251.067
• InChiKey: XHXIRIYXDGWLJN-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,5-已二烯 在 碘 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (2R*,5S*)-2-(cyano-methyl)-5-(iodomethyl)tetrahydrofuran
  参考文献：
  名称：

  Tetrahydrofurans via isoxazoline: a tandem 1,3-dipolar cycloaddition/electrophilic cyclization sequence

  摘要：

  DOI：

  10.1021/ja00258a078

文献信息

• Tandem 1,3-dipolar cycloaddition and electrophilic cyclization reactions: cyclic ether subunits of polyether antibiotics from unsaturated isoxazolines
  作者：Mark J. Kurth、Marilyn M. Olmstead、Michael J. Rodriguez

  DOI：10.1021/jo00288a047

  日期：1990.1
• Polymer-Supported Synthesis of Cyclic Ethers: Electrophilic Cyclization of Isoxazolines
  作者：Xenia Beebe、Neil E. Schore、Mark J. Kurth

  DOI：10.1021/jo00118a041

  日期：1995.6

  Polymer-supported synthesis of 2,5-disubstituted tetrahydrofurans via tandem 1,3-dipolar cycloaddition/electrophilic cyclization has been accomplished using a five-step reaction sequence to give 2-(cyanomethyl)-5-(iodomethyl)tetrahydrofuran (cis:trans ratio of 1:2) in 40% overall yield. The corresponding 2-(cyanomethyl)-6-(iodomethyl)tetrahydro was similarly formed in a 7% overall yield. The final electrophilic cyclization simultaneously releases the desired product and regenerates the initial polymer-bound functionality. In the process the desired cyclic ether is obtained exclusively; byproducts of the sequence are not cleaved from the polymer support. In addition the polymer support is sufficiently robust to be recovered and recycled through the reaction sequence.