(+/-)-4-(3-Bromo-2-methylpropyl)-1-<(tert-butyldimethylsilyl)oxy>-2,6-dimethylbenzene | 118631-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-4-(3-Bromo-2-methylpropyl)-1-<(tert-butyldimethylsilyl)oxy>-2,6-dimethylbenzene
• 英文别名: [4-(3-Bromo-2-methylpropyl)-2,6-dimethylphenoxy]-tert-butyl-dimethylsilane
• CAS: 118631-01-9
• 化学式: C₁₈H₃₁BrOSi
• 分子量: 371.433
• InChiKey: JKMSYLMHFQOTFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(3-Bromo-2-methylpropyl)-1-<(tert-butyldimethylsilyl)oxy>-2,6-dimethylbenzene 在 正丁基锂 、 四丁基氟化铵 、 sodium hydride 、 zinc(II) chloride 、 silver(l) oxide 作用下， 以 四氢呋喃 、 氘代氯仿 、 正己烷 为溶剂， 反应 44.5h， 生成 (1R*,2S*,3R*)-2-(3,5-Dimethyl-4-hydroxyphenyl)-3-methyl-6-oxocyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions

  摘要：

  p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2,6-disubstituted phenols with Ag2O afforded the corresponding quinone methides. A wide range of cyclization terminators/nucleophiles were found to be effective in the cyclizations, including: allylsilane, beta-keto esters, furan, pyrrole, indole, and a number of alkenes. The yields of the cyclizations were generally high.

  DOI：

  10.1021/jo00100a039
• 作为产物：
  描述：

  (+/-)-3-<4-<(tert-Butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-2-methyl-1-propanol 在 四溴化碳 、 三苯基膦 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 (+/-)-4-(3-Bromo-2-methylpropyl)-1-<(tert-butyldimethylsilyl)oxy>-2,6-dimethylbenzene
  参考文献：
  名称：

  Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions

  摘要：

  p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2,6-disubstituted phenols with Ag2O afforded the corresponding quinone methides. A wide range of cyclization terminators/nucleophiles were found to be effective in the cyclizations, including: allylsilane, beta-keto esters, furan, pyrrole, indole, and a number of alkenes. The yields of the cyclizations were generally high.

  DOI：

  10.1021/jo00100a039

文献信息

• Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+, J. Org. Chem, 59 (1994) N 21, S 6322-6337
  作者：Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+

  DOI：——

  日期：——
• Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions
  作者：Steven R. Angle、Damian O. Arnaiz、James P. Boyce、Rogelio P. Frutos、Michael S. Louie、Heather L. Mattson-Arnaiz、Jon D. Rainier、Kenneth D. Turnbull、Wenjin Yang

  DOI：10.1021/jo00100a039

  日期：1994.10

  p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2,6-disubstituted phenols with Ag2O afforded the corresponding quinone methides. A wide range of cyclization terminators/nucleophiles were found to be effective in the cyclizations, including: allylsilane, beta-keto esters, furan, pyrrole, indole, and a number of alkenes. The yields of the cyclizations were generally high.