1-[2-Bromo-5-[tert-butyl(dimethyl)silyl]oxycyclopenten-1-yl]hexan-1-ol | 892145-17-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-[2-Bromo-5-[tert-butyl(dimethyl)silyl]oxycyclopenten-1-yl]hexan-1-ol
• 英文别名: 1-[2-bromo-5-[tert-butyl(dimethyl)silyl]oxycyclopenten-1-yl]hexan-1-ol
• CAS: 892145-17-4
• 化学式: C₁₇H₃₃BrO₂Si
• 分子量: 377.437
• InChiKey: VMMWJGUNEFJMPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-Bromo-5-[tert-butyl(dimethyl)silyl]oxycyclopenten-1-yl]hexan-1-ol 、 乙醛 在 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 6.0h， 以76%的产率得到1-[5-(tert-Butyl-dimethyl-silanyloxy)-2-(1-hydroxy-ethyl)-cyclopent-1-enyl]-hexan-1-ol
  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 咪唑 、 4-二甲氨基吡啶 、 potassium iodate 、 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride 、 草酰溴 、 氢碘酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.95h， 生成 1-[2-Bromo-5-[tert-butyl(dimethyl)silyl]oxycyclopenten-1-yl]hexan-1-ol
  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

文献信息

• 1,2-Bisanionic Coupling Approach to 2,3-Disubstituted Cyclopentenols and Cyclopentenones
  作者：Marco Luparia、Alessandro Vadalà、Giuseppe Zanoni、Giovanni Vidari

  DOI：10.1021/ol060654y

  日期：2006.5.1

  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.