[4-(Bromomethyl)-2,6-dimethoxyphenoxy]-tert-butyl-dimethylsilane | 158555-49-8

• 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-(Bromomethyl)-2,6-dimethoxyphenoxy]-tert-butyl-dimethylsilane
• CAS: 158555-49-8
• 化学式: C₁₅H₂₅BrO₃Si
• 分子量: 361.351
• InChiKey: AHJFGFMKAUEBLV-UHFFFAOYSA-N

物化性质

• 沸点：
  376.5±42.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [4-(Bromomethyl)-2,6-dimethoxyphenoxy]-tert-butyl-dimethylsilane 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.25h， 生成 1-<(tert-Butyldimethylsilyl)oxy>-2,6-dimethoxy-4-<4-butyl>benzene
  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：

  丁香醛 在 咪唑 、 sodium tetrahydroborate 、 三甲基溴硅烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [4-(Bromomethyl)-2,6-dimethoxyphenoxy]-tert-butyl-dimethylsilane
  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

• Antineoplastic Agents. 579. Synthesis and Cancer Cell Growth Evaluation of <i>E</i>-Stilstatin 3: A Resveratrol Structural Modification
  作者：George R. Pettit、Noeleen Melody、Andrew Thornhill、John C. Knight、Thomas L. Groy、Cherry L. Herald

  DOI：10.1021/np9002146

  日期：2009.9.25

  As an extension of our earlier structure/activity investigation of resveratrol (1a) cancer cell growth inhibitory activity compared to the structurally related stilbene combretastatin series (e.g., 2a), an efficient synthesis of E-stilstatin 3 (3a) and its phosphate prodrug 3b was completed. The trans-stilbene 3a was obtained using a convergent synthesis employing a Wittig reaction with phosphonium

  作为我们早期对白藜芦醇 ( 1a ) 癌细胞生长抑制活性与结构相关的芪康布他汀系列 (例如，2a )相比的结构/活性研究的延伸，E- stilstatin 3 ( 3a ) 及其磷酸盐前药3b的有效合成完成了。的反式均二苯乙烯3A使用采用与溴化鏻进行Wittig反应汇集合成，得到9作为关键反应步骤。Z-甲硅烷基醚13 的脱保护得到E- stilstatin 3 ( 3a) 作为独家产品。3a的结构和立体化学通过 X 射线晶体结构测定得到证实。
• Palladium-Catalyzed Intramolecular<i>ipso</i>-Friedel-Crafts Allylic Alkylation of Phenols<i>via</i>Arylative Activation of Allenes
  作者：Tetsuhiro Nemoto、Tomoyuki Nozaki、Mariko Yoshida、Yasumasa Hamada

  DOI：10.1002/adsc.201300326

  日期：2013.9.16

  A novel and efficient synthetic method for functionalized spiro[4.5]cyclohexadienones was developed based on the palladium‐catalyzed sequential process: Heck insertion to an allene–intramolecular ipso‐Friedel–Crafts allylic alkylation cascade. Using 5 mol% of palladium catalyst, a wide variety of spirocycles was obtained in good to excellent yields. The developed cascade process was also applicable

  一种新颖的和官能化的螺高效合成法[4.5]环己二烯酮是基于钯催化的顺序过程开发：赫克插入到丙二烯分子内本位-Friedel -克拉夫茨烯丙基烷基化级联。使用5mol％的钯催化剂，以良好至优异的产率获得了多种螺环。所开发的级联方法也适用于四氢萘衍生物的合成。
• 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.