(1E,3S,4R)-5-acetoxy-3,4-epoxy-1-iodo-2,3-dimethyl-1-pentene | 1330680-63-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E,3S,4R)-5-acetoxy-3,4-epoxy-1-iodo-2,3-dimethyl-1-pentene
• CAS: 1330680-63-1
• 化学式: C₉H₁₃IO₃
• 分子量: 296.105
• InChiKey: OOMHBOSWKNMPKZ-OGSWXMBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (1E,3S,4R)-5-acetoxy-3,4-epoxy-2,3-dimethyl-1-triisopropylsilyl-1-pentene 在 N-碘代丁二酰亚胺 作用下， 以 六氟异丙醇 为溶剂， 以90%的产率得到(1E,3S,4R)-5-acetoxy-3,4-epoxy-1-iodo-2,3-dimethyl-1-pentene
  参考文献：
  名称：

  Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D

  摘要：

  The C-Si bonds of triisopropylsilyl-substituted alkenes, 1,3-dienes, and related multifunctional substrates, as well as analogous C-TBDPS and C-TBS bonds, are readily and chemoselectively cleaved with NIS (or other sources of I(+), such as N-iodosaccharin, 1,3-diodohydantoin, and Ipy(2)BF(4)). The desired iodoalkenes are obtained stereospecifically without byproducts, provided that the reactions are carried out in CF(3)CHOHCF(3) and, in general, with 30 mol % of Ag(2)CO(3) (or AgOAc/2,6-Iutidine) as an additive. Fragment C10-C18 of cytotoxic amphidinolides B1-B3 and D has been synthesized using this improved procedure.

  DOI：

  10.1021/ol2020187