4-(tert-butyldimethylsilyloxy)-3,5-dimethoxybenzyl alcohol | 141327-85-7

• 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-(tert-butyldimethylsilyloxy)-3,5-dimethoxybenzyl alcohol
• 英文别名: [4-[Tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxyphenyl]methanol
• CAS: 141327-85-7
• 化学式: C₁₅H₂₆O₄Si
• 分子量: 298.455
• InChiKey: VAYOHGFNJHGIPC-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  373.8±42.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 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：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(tert-butyldimethylsilyloxy)-3,5-dimethoxybenzyl alcohol 在 三甲基溴硅烷 、 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 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(tert-butyldimethylsilyloxy)-3,5-dimethoxybenzyl alcohol
  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

• Highly sulphated cellulose: a versatile, reusable and selective desilylating agent for deprotection of alcoholic TBDMS ethers
  作者：Soma Shekar Dachavaram、Narsimha R. Penthala、Julie L. Calahan、Eric J. Munson、Peter A. Crooks

  DOI：10.1039/c8ob01438h

  日期：——

  A mild, efficient and rapid protocol was developed for the deprotection of alcoholic TBDMS ethers using a recyclable, eco-friendly highly sulphated cellulose sulphate acid catalyst in methanol. This acid catalyst selectively cleaves alcoholic TBDMS ethers in bis-TBDMS ethers containing both alcoholic and phenolic TBDMS ether moieties.

  开发了一种温和，有效和快速的方案，使用可回收的，环境友好的高度硫酸化的硫酸纤维素硫酸酯催化剂在甲醇中脱醇TBDMS醚。该酸催化剂在含有醇和酚TBDMS醚部分的双-TBDMS醚中选择性裂解醇TBDMS醚。
• 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。