(benzyloxy)diisopropylsilane | 503071-46-3

• 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: (benzyloxy)diisopropylsilane
• 英文别名: benzyloxydiisopropylsilane；Phenylmethoxy-di(propan-2-yl)silane
• CAS: 503071-46-3
• 化学式: C₁₃H₂₂OSi
• 分子量: 222.403
• InChiKey: SFZJFCZUMYRPGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (benzyloxy)diisopropylsilane 在 正丁基锂 、 三氯异氰尿酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 1-(3-((benzyloxy)diisopropylsilyl)phenyl)cyclopentanecarbonitrile
  参考文献：
  名称：

  Meta-Selective C–H Functionalization Using a Nitrile-Based Directing Group and Cleavable Si-Tether

  摘要：

  A nitrile-based template that enables metaselective C-H bond functionalization was developed. The template is applicable to a range of substituted arenes and tolerates a variety of functional groups. The directing group uses a silicon atom for attachment, allowing for a facile introduction/deprotection strategy increasing the synthetic practicality of this template.

  DOI：

  10.1021/ja4107034
• 作为产物：
  描述：

  二异丙基氯代硅烷 、 苯甲醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以28%的产率得到(benzyloxy)diisopropylsilane
  参考文献：
  名称：

  Pincer Ruthenium Catalyzed Intramolecular Silylation of C(sp2)–H Bonds

  摘要：

  本文报告了一种由一种夹环钌配合物催化的高效分子内芳香族C-H键硅化反应，以相对温和的反应条件在广泛底物范围和低催化剂负载下生成苯氧硅烷类化合物。硅化产物可以通过Pd催化的Hiyama-Denmark交叉偶联反应进一步转化为联苯产物。

  DOI：

  10.1055/s-0036-1590982

文献信息

• Modular Approach to Reductive C_sp2–H and C_sp3–H Silylation of Carboxylic Acid Derivatives through Single-Pot, Sequential Transition Metal Catalysis
  作者：Yuanda Hua、Seongjeong Jung、James Roh、Junha Jeon

  DOI：10.1021/acs.joc.5b00564

  日期：2015.5.1

  modular approach to catalytic reductive Csp2–H and Csp3–H silylation of carboxylic acid derivatives encompassing esters, ketones, and aldehydes. Choice of either an Ir(I)/Rh(I) or Rh(I)/Rh(I) sequence leads to either exhaustive reductive ester or reductive ketone/aldehyde silylation, respectively. Notably, a catalyst-controlled direct formation of doubly reduced silyl ethers is presented, specifically

  我们报告了一种模块化方法，用于催化还原性C sp2- H和C sp3- H甲酸酯基，包括酯，酮和醛的羧酸衍生物的甲硅烷基化。Ir（I）/ Rh（I）或Rh（I）/ Rh（I）序列的选择分别导致详尽的还原性酯或还原性酮/醛甲硅烷基化。值得注意的是，提出了一种催化剂控制的直接还原的双还原甲硅烷基醚的形成方法，特别是通过Ir催化的详尽的氢化硅烷化反应。生成的甲硅烷基醚在单个容器中进行C sp2- H和苄基C sp3- H甲硅烷基化。
• Modular Synthesis of (Borylmethyl)silanes through Orthogonal Functionalization of a Carbon Atom
  作者：Rajdip Chowdhury、Gábor Zoltán Elek、Beatriz Meana-Baamonde、Abraham Mendoza

  DOI：10.1021/acs.orglett.3c00474

  日期：2023.3.24

  building blocks in organic synthesis displaying a unique reactivity. Yet, the synthesis of more advanced derivatives is limited by the advanced silicon intermediates required for their preparation. Herein, a one-pot synthesis of (borylmethyl)silanes is developed, sourced on available alkyl-, aryl-, alkoxy-, aryloxy-, and silyl-hydrosilane materials. The privileged reactivity of N-hydroxyphthalimidyl diazoacetate

  (Borylmethyl)trimethylsilanes 是有机合成中的重要组成部分，显示出独特的反应性。然而，更高级衍生物的合成受到制备它们所需的高级硅中间体的限制。在此，基于可用的烷基-、芳基-、烷氧基-、芳氧基-和甲硅烷基-氢硅烷材料，开发了 (borylmethyl) 硅烷的一锅法合成。仔细研究了N-羟基邻苯二甲酰亚胺基重氮乙酸酯 (NHPI-DA) 在 Si-H 插入和 α-甲硅烷基氧化还原活性酯在不同脱羧硼化反应中的特殊反应性。
• Etherification of alkoxydialkylsilanes with carbonyl compounds
  作者：Xinglong Jiang、Joginder S Bajwa、Joel Slade、Kapa Prasad、Oljan Repič、Thomas J Blacklock

  DOI：10.1016/s0040-4039(02)02253-0

  日期：2002.12

  A novel method for preparing ethers from alkoxydialkylsilanes and carbonyl compounds through reductive etheritication is described. The salient feature in this method is the utilization of internal hydrogen as the hydride source for reducing the oxonium intermediate generated by using the Cl(R)(2)SiBr[BiBr3/Cl(R)(2)SiH] catalytic system. (C) 2002 Published by Elsevier Science Ltd.
• Pincer Ruthenium Catalyzed Intramolecular Silylation of C(sp2)–H Bonds
  作者：Zheng Huang、Huaquan Fang、Qiaoxing He、Guixia Liu

  DOI：10.1055/s-0036-1590982

  日期：2017.11

  Reported herein is a highly efficient intramolecular silylation of aromatic C–H bonds catalyzed by a pincer ruthenium complex, giving benzoxasiloles under relatively mild reaction conditions with broad substrate scope and low catalyst loadings. The silylation product can be further converted into a biaryl product by Pd-catalyzed Hiyama–­Denmark cross-coupling reactions.

  本文报告了一种由一种夹环钌配合物催化的高效分子内芳香族C-H键硅化反应，以相对温和的反应条件在广泛底物范围和低催化剂负载下生成苯氧硅烷类化合物。硅化产物可以通过Pd催化的Hiyama-Denmark交叉偶联反应进一步转化为联苯产物。
• Meta-Selective C–H Functionalization Using a Nitrile-Based Directing Group and Cleavable Si-Tether
  作者：Sunggi Lee、Hyelee Lee、Kian L. Tan

  DOI：10.1021/ja4107034

  日期：2013.12.18

  A nitrile-based template that enables metaselective C-H bond functionalization was developed. The template is applicable to a range of substituted arenes and tolerates a variety of functional groups. The directing group uses a silicon atom for attachment, allowing for a facile introduction/deprotection strategy increasing the synthetic practicality of this template.