6-bromo-6-(tributylstannyl)hexanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-6-(tributylstannyl)hexanal
• 化学式: C₁₈H₃₇BrOSn
• 分子量: 468.105
• InChiKey: BOMMGMHISKPBMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-6-(tributylstannyl)hexanal 、 烯丙基三丁基锡 在 六正丁基二锡 作用下， 反应 8.0h， 以10%的产率得到2-allylcyclohexanol
  参考文献：
  名称：

  A Novel 1,3-Stannyl Shift Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group

  摘要：

  [GRAPHICS]Reactions of alpha-stannyl bromides and xanthates with tributyltin hydride generate a stannyl radicals, Intramolecular cyclizations of these radicals with a formyl group afford gamma-stannyl alkoxy radicals that undergo a 1,3-stannyl shift from carbon to oxygen. The carbon radicals obtained can be trapped inter- or intramolecularly. Approximately, the rates of 5-exo cyclizations of alpha-stannyl radicals with a formyl group and terminal olefin are similar.

  DOI：

  10.1021/ol990199o

文献信息

• The Scope and Limitations of 1,3-Stannyl Shift-Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group
  作者：Shau-Hua Ueng、Ming-Jen Chen、Shu-Fang Chu、Yar-Fang Shao、Gang-Ting Fan、Sheng-Yueh Chang、Yeun-Min Tsai

  DOI：10.1021/jo052176v

  日期：2006.2.1

  and serves as a driving force to promote the cyclizations. Although the cyclization rates can be accelerated when the formyl group carries α-dimethyl substituents, unfortunately β-scission of the alkoxy radicals becomes competitive with the 1,3-stannyl shift. The β-stannyloxy radicals can be employed in further cyclizations to obtain tandem cyclization products.

  α-三丁基锡烷基可以由相应的溴化物或黄药生成。这些基团经过带有甲酰基的有效分子内1，5-环化反应。所得的β-锡烷基烷氧基通过从碳到氧的1，3-锡烷基转移进行，以提供β-锡烷基氧基。这种新颖的重排极有可能是不可逆的，并且是促进环化的驱动力。尽管当甲酰基带有α-二甲基取代基时可以加快环化速率，但是不幸的是，烷氧基的β-断裂与1，3-锡烷基移位竞争。可以将β-锡烷基氧基用于进一步的环化以获得串联环化产物。
• A Novel 1,3-Stannyl Shift Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group
  作者：Sheng-Yueh Chang、Yar-Fang Shao、Shu-Fang Chu、Gang-Ting Fan、Yeun-Min Tsai

  DOI：10.1021/ol990199o

  日期：1999.9.1

  [GRAPHICS]Reactions of alpha-stannyl bromides and xanthates with tributyltin hydride generate a stannyl radicals, Intramolecular cyclizations of these radicals with a formyl group afford gamma-stannyl alkoxy radicals that undergo a 1,3-stannyl shift from carbon to oxygen. The carbon radicals obtained can be trapped inter- or intramolecularly. Approximately, the rates of 5-exo cyclizations of alpha-stannyl radicals with a formyl group and terminal olefin are similar.