3-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethylphenyl)propan-1-ol | 118631-05-3

• 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: 3-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethylphenyl)propan-1-ol
• 英文别名: 3-[4-[Tert-butyl(dimethyl)silyl]oxy-3,5-dimethylphenyl]propan-1-ol
• CAS: 118631-05-3
• 化学式: C₁₇H₃₀O₂Si
• 分子量: 294.51
• InChiKey: RIUNKLUEEFIRKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethylphenyl)propan-1-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以58%的产率得到3-<4-<(tert-Butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-1-propanal
  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：

  硅烷,(1,1-二甲基乙基)[2,6-二甲基-4-(2-丙烯基)苯氧基]二甲基- 在 sodium hydroxide 、 硼烷 、 双氧水 作用下， 生成 3-(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethylphenyl)propan-1-ol
  参考文献：
  名称：

  甲基对苯醌引发的分子内亲电取代反应

  摘要：

  提出了对-醌甲基化物在分子内环化反应中的反应性的研究。的对位-quinone甲基化物进行分离和前环化完全表征。呋喃，吡咯和单烷基取代的苯用作环化终止剂。

  DOI：

  10.1016/s0040-4039(00)72713-4

文献信息

• A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents
  作者：Xiaofeng Ma、Joshua J. Farndon、Tom A. Young、Natalie Fey、John F. Bower

  DOI：10.1002/anie.201708176

  日期：2017.11.13

  A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.

  概述了具有广泛范围的 CN 键形成脱芳构化方案。具体来说，双功能氨基试剂用于顺序亲核和亲电CN键形成，后者影响关键的脱芳构化步骤。使用这种方法，只需两到三个步骤即可将 γ-芳基化醇转化为各种差异保护的螺环吡咯烷。
• Para-quinone methide initiated intramolecular electrophilic substitution reactions
  作者：Steven R. Angle、Michael S. Louie、Heather L. Mattson、Wenjin Yang

  DOI：10.1016/s0040-4039(00)72713-4

  日期：1989.1

  A study on the reactivity of para-quinone methides in intramolecular cyclization reactions is presented. The para-quinone methides were isolated and completely characterized prior to cyclization. A furan, a pyrrole and a mono-alkyl substituted benzene were used as cyclization terminators.

  提出了对-醌甲基化物在分子内环化反应中的反应性的研究。的对位-quinone甲基化物进行分离和前环化完全表征。呋喃，吡咯和单烷基取代的苯用作环化终止剂。
• Transition Metal Free C–N Bond Forming Dearomatizations and Aryl C–H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent
  作者：Joshua J. Farndon、Xiaofeng Ma、John F. Bower

  DOI：10.1021/jacs.7b07830

  日期：2017.10.11

  We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C-N bond forming dearomatization or aryl C-H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines.
• 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.