(4-methoxyphenyl)triisopropylsilane | 14311-77-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4-methoxyphenyl)triisopropylsilane
• 英文别名: triisopropyl(4-methoxyphenyl)silane；1-methoxy-4-triisopropylsilylbenzene；<4-Methoxy-phenyl>-triisopropyl-silan；(4-Methoxyphenyl)-tri(propan-2-yl)silane
• CAS: 14311-77-4
• 化学式: C₁₆H₂₈OSi
• 分子量: 264.483
• InChiKey: IMUVIIJVRLWACU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三异丙基氯硅烷 在 sodium tetrahydroborate 、 9,10-二甲氧基蒽 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 19.0h， 生成 (4-methoxyphenyl)triisopropylsilane
  参考文献：
  名称：

  通过有机光氧化还原催化对芳烃进行 p-甲硅烷基化：使用 p-甲硅烷基化芳烃进行专有的 o-甲硅烷基化、o-酰化和 o-烷基化反应

  摘要：

  通过将原位生成的甲硅烷基自由基与芳烃自由基阳离子偶联，已经实现了芳烃的光催化区域特异性p-甲硅烷基化。该策略包括 PhSe-SiR 3 的还原活化和从富电子芳烃到 9,10-二甲氧基蒽自由基阳离子 (DMA •+ ) 的单电子转移。如此形成的对-甲硅烷基芳烃进一步用于排他性的o-甲硅烷基化反应和区域特异性的o-酰化以及o-烷基化反应。

  DOI：

  10.1021/acs.orglett.1c02672

文献信息

• Diphenylsilylsilanolates Enable the Transfer of a Wide Range of Silyl Groups
  作者：Hiroki Yamagishi、Fuyuki Harata、Jun Shimokawa、Hideki Yorimitsu

  DOI：10.1021/acs.orglett.2c03558

  日期：2023.1.13

  Development of silylating reagents that can transfer a wide range of silyl groups has been a long-standing challenge. Herein we report sodium diphenylsilylsilanolates as new stable and handy silylating reagents that could be synthesized from chlorosilanes. The new reagents retain the ability of dimethylsilylsilanolates for the delivery of a variety of silyl groups in palladium-catalyzed silylation

  开发可转移多种甲硅烷基的甲硅烷基化试剂一直是一项长期挑战。在这里，我们报告了二苯基甲硅烷基硅烷醇钠作为新型稳定且方便的甲硅烷基化试剂，可以从氯硅烷合成。新试剂保留了二甲基甲硅烷基硅烷醇盐在钯催化的芳基溴甲硅烷基化反应中传递各种甲硅烷基的能力，而不管要转移的甲硅烷基的空间和电子特性如何。
• Direct and Selective Arylation of Tertiary Silanes with Rhodium Catalyst
  作者：Yoshinori Yamanoi、Hiroshi Nishihara

  DOI：10.1021/jo8008148

  日期：2008.9.1

  We have developed a convenient and efficient approach to the arylation of tertiary silanes under mild conditions. A variety of arylsilanes were synthesized in a one-step process with good to excellent yields in the presence of a rhodium catalyst with a base. The reaction was highly solvent dependent, and amides were the most effective of the various solvents used. This common catalyst system is highly tolerant of the various sensitive functional groups on the substrates, which might be difficult to extract by other methods. The rhodium-promoted silylation of aryl halides with electron-donating groups occurred more efficiently than the silylation of aryl halides substituted with electron-withdrawing groups. Heteroaromatic halides were also found to be readily silylated with tertiary silanes. The successful application of this reaction to the synthesis of a TAC-101 analogue, which is a trialkylsilyl-containing synthetic retinoid benzoic acid derivative with selective binding affinity for retinoic acid receptor-alpha, is also described.