6-溴-9-甲基-1,4-二氧杂螺[4.4]壬-6-烯 | 208450-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-溴-9-甲基-1,4-二氧杂螺[4.4]壬-6-烯
• 英文名称: 6-bromo-9-methyl-1,4-dioxaspiro[4.4]non-6-ene
• 英文别名: 9-bromo-6-methyl-1,4-dioxaspiro[4.4]non-8-ene
• CAS: 208450-52-6
• 化学式: C₈H₁₁BrO₂
• 分子量: 219.078
• InChiKey: DZINRPUBDXIJNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-溴-9-甲基-1,4-二氧杂螺[4.4]壬-6-烯 在 正丁基锂 、 硫酸 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-5-Methyl-2-(2,4,6-triisopropyl-benzenesulfinyl)-cyclopent-2-enone
  参考文献：
  名称：

  Diastereomer-Differentiating Radical β-Addition to 4- or 5-Methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones

  摘要：

  Addition of alkyl radicals to a diastereomeric mixture of(4R)- and (4S)-4-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones gave the diastereomerically pure addition product derived from the (4R)-isomer, while the (4S)-isomer remained unreacted. The tel tert-butyl radical addition to a diastereomeric mixture of (5R)- and (5S)-5-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2- cyclopentenones also gave the diastereomerically pure addition product. These results show that (4R) and (4S) or (5R) and (5S) diastereomers were kinetically separated in the radical beta-addition. The 1,2- and 1,3-steric interactions in the radical addition to 4- or 5-methyl-2-cyclopentenones were also examined.

  DOI：

  10.1021/jo9721507
• 作为产物：
  描述：

  5-甲基环戊-2-烯-1-酮 、 乙二醇 在 溴 、 对甲苯磺酸 、 三乙胺 作用下， 生成 6-溴-9-甲基-1,4-二氧杂螺[4.4]壬-6-烯
  参考文献：
  名称：

  Diastereomer-Differentiating Radical β-Addition to 4- or 5-Methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones

  摘要：

  Addition of alkyl radicals to a diastereomeric mixture of(4R)- and (4S)-4-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones gave the diastereomerically pure addition product derived from the (4R)-isomer, while the (4S)-isomer remained unreacted. The tel tert-butyl radical addition to a diastereomeric mixture of (5R)- and (5S)-5-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2- cyclopentenones also gave the diastereomerically pure addition product. These results show that (4R) and (4S) or (5R) and (5S) diastereomers were kinetically separated in the radical beta-addition. The 1,2- and 1,3-steric interactions in the radical addition to 4- or 5-methyl-2-cyclopentenones were also examined.

  DOI：

  10.1021/jo9721507

文献信息

• Diastereomer-Differentiating Radical β-Addition to 4- or 5-Methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones
  作者：Nobuyuki Mase、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1021/jo9721507

  日期：1998.6.1

  Addition of alkyl radicals to a diastereomeric mixture of(4R)- and (4S)-4-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones gave the diastereomerically pure addition product derived from the (4R)-isomer, while the (4S)-isomer remained unreacted. The tel tert-butyl radical addition to a diastereomeric mixture of (5R)- and (5S)-5-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2- cyclopentenones also gave the diastereomerically pure addition product. These results show that (4R) and (4S) or (5R) and (5S) diastereomers were kinetically separated in the radical beta-addition. The 1,2- and 1,3-steric interactions in the radical addition to 4- or 5-methyl-2-cyclopentenones were also examined.