7-Bromo-6-iodo-1,4-dioxa-spiro[4.4]non-6-ene | 892145-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Bromo-6-iodo-1,4-dioxa-spiro[4.4]non-6-ene
• CAS: 892145-37-8
• 化学式: C₇H₈BrIO₂
• 分子量: 330.948
• InChiKey: TVFCSOKAMXZRMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7-Bromo-6-iodo-1,4-dioxa-spiro[4.4]non-6-ene 在 叔丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 6.0h， 以75%的产率得到7-Bromo-1,4-dioxa-spiro[4.4]non-6-ene
  参考文献：
  名称：

  1,2-Bisanionic Coupling Approach to 2,3-Disubstituted Cyclopentenols and Cyclopentenones

  摘要：

  We describe a new approach to 2,3-disubstituted cyclopentenols and cyclopentenones through two consecutive regioselective additions of equal or different electrophiles to a cyclopentene bisanionic synthon. Indeed, on exposure to BuLi, 3-bromo-2-iodocyclopent-2-enol O-TBS ether undergoes iodine-lithium permutation with complete regioselectivity. Successive reaction of the monolithium anion with different C(sp(2))and C(sp(3))-electrophiles affords the corresponding 2-substituted-3-bromocyclopentenol derivative. Subsequent bromo-lithium exchange with t-BuLi, followed by reaction with an equal or different electrophile, affords the desired 2,3-disubstituted cyclopentenol.

  DOI：

  10.1021/ol060654y
• 作为产物：
  描述：

  1,3-环戊二酮 在 potassium iodate 、 草酰溴 、 氢碘酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 7-Bromo-6-iodo-1,4-dioxa-spiro[4.4]non-6-ene
  参考文献：
  名称：

  1,2-Bisanionic Coupling Approach to 2,3-Disubstituted Cyclopentenols and Cyclopentenones

  摘要：

  We describe a new approach to 2,3-disubstituted cyclopentenols and cyclopentenones through two consecutive regioselective additions of equal or different electrophiles to a cyclopentene bisanionic synthon. Indeed, on exposure to BuLi, 3-bromo-2-iodocyclopent-2-enol O-TBS ether undergoes iodine-lithium permutation with complete regioselectivity. Successive reaction of the monolithium anion with different C(sp(2))and C(sp(3))-electrophiles affords the corresponding 2-substituted-3-bromocyclopentenol derivative. Subsequent bromo-lithium exchange with t-BuLi, followed by reaction with an equal or different electrophile, affords the desired 2,3-disubstituted cyclopentenol.

  DOI：

  10.1021/ol060654y