6-Bromo-1-[(4-methoxy-phenyl)-dimethyl-silanyl]-hexan-1-one | 202349-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-Bromo-1-[(4-methoxy-phenyl)-dimethyl-silanyl]-hexan-1-one
• 英文别名: 6-Bromo-1-[(4-methoxyphenyl)-dimethylsilyl]hexan-1-one
• CAS: 202349-31-3
• 化学式: C₁₅H₂₃BrO₂Si
• 分子量: 343.336
• InChiKey: NPUKQJYKLTYHEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Bromo-1-[(4-methoxy-phenyl)-dimethyl-silanyl]-hexan-1-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以81%的产率得到Cyclohexyloxy-(4-methoxy-phenyl)-dimethyl-silane
  参考文献：
  名称：

  The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals

  摘要：

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.

  DOI：

  10.1021/jo9711302
• 作为产物：
  描述：

  chlorodimethyl(4-methoxyphenyl)silane 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 6-Bromo-1-[(4-methoxy-phenyl)-dimethyl-silanyl]-hexan-1-one
  参考文献：
  名称：

  The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals

  摘要：

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.

  DOI：

  10.1021/jo9711302

文献信息

• The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals
  作者：Sheng-Yueh Chang、Weir-Torn Jiaang、Chaur-Donp Cherng、Kuo-Hsiang Tang、Chih-Hao Huang、Yeun-Min Tsai

  DOI：10.1021/jo9711302

  日期：1997.12.1

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.