4-tert-Butyl-phenyl-silane | 63128-19-8

• 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-tert-Butyl-phenyl-silane
• 英文别名: (4-tert-Butylphenyl)silane；(4-tert-butylphenyl)silane
• CAS: 63128-19-8
• 化学式: C₁₀H₁₆Si
• 分子量: 164.323
• InChiKey: RPRUHXDTWVNJSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  CIS,CIS-1,3,5-CYCLOHEXANETRIOL DIHYDRATE 、 4-tert-Butyl-phenyl-silane 在 Wilkinson's catalyst 作用下， 以 苯 为溶剂， 反应 18.0h， 以55%的产率得到1-(4-tert-Butyl-phenyl)-2,8,9-trioxa-1-sila-tricyclo[3.3.1.1^3,7]decane
  参考文献：
  名称：

  A Novel Synthesis of 2,4,10-Trioxa-3-silaadamantanes

  摘要：

  DOI：

  10.1055/s-1984-30907
• 作为产物：
  描述：

  Trichlor-<4-tert-butyl-phenyl>-silan 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以77%的产率得到4-tert-Butyl-phenyl-silane
  参考文献：
  名称：

  A Novel Synthesis of 2,4,10-Trioxa-3-silaadamantanes

  摘要：

  DOI：

  10.1055/s-1984-30907

文献信息

• Enantioselective synthesis of acyclic monohydrosilanes by steric hindrance assisted C–H silylation
  作者：Delong Mu、Shuqiong Pan、Xiaoyu Wang、Xiaoyun Liao、Yong Huang、Jiean Chen

  DOI：10.1039/d2cc02307e

  日期：——

  Herein, a rhodium-catalyzed desymmetrization of dihydrosilanes with heterocyclic compounds via intermolecular dehydrogenative C–H silylation is developed.

  在此，开发了一种通过铑催化的二氢硅烷与杂环化合物的不对称化反应，通过分子间脱氢C-H硅化反应实现。
• Enantioselective Nickel‐Catalyzed Hydrosilylation of 1,1‐Disubstituted Allenes
  作者：Tao Liu、Xin‐Rui Mao、Shuo Song、Zi‐Yang Chen、Yichen Wu、Li‐Ping Xu、Peng Wang

  DOI：10.1002/anie.202216878

  日期：2023.3.6

  SPSiOL-base bisphosphite ligand (SPSiPO), Ni-catalyzed asymmetric hydrosilylation of 1,1-disubstituted allenes was realized for the first time, delivering the enantioenriched allylsilanes bearing a tertiary carbon stereocenter in high efficiency and 100 % atom-economy with high chemo-, regio- and enantioselectivities.

  使用新开发的基于 SPSiOL 的双亚磷酸酯配体 (SPSiPO)，首次实现了 Ni 催化的 1,1-二取代丙二烯的不对称氢化硅烷化反应，以高效率和 100% 原子经济性提供带有叔碳立构中心的对映体富集的烯丙基硅烷具有高化学选择性、区域选择性和对映选择性。
• Selective Access to Silacyclopentanes and Homoallylsilanes by La-Catalyzed Hydrosilylations of 1-Aryl Methylenecyclopropanes
  作者：Xiaoming Xu、Ailin Gao、Xiufang Xu、Jianfeng Li、Chunming Cui

  DOI：10.1021/jacs.3c12355

  日期：2024.2.14

  their unique reactivity. However, metal-catalyzed hydrosilylation of MCPs has met with very limited successes. In this paper, catalytic selective hydrosilylations of MCPs with some primary silanes using an ene-diamido lanthanum ate complex as the catalyst were described. The catalytic reactions resulted in the selective formation of silacyclopentanes and (E)-homoallylsilanes, respectively, depending on

  亚甲基环丙烷 (MCP) 因其独特的反应性而成为合成化学中的多功能构件。然而，金属催化的 MCP 氢化硅烷化反应取得的成功非常有限。本文描述了使用烯-二酰氨基镧酸酯络合物作为催化剂，MCP 与一些伯硅烷的选择性催化氢化硅烷化反应。根据 MCP 上的取代基，催化反应分别选择性地形成硅杂环戊烷和 ( E )-高烯丙基硅烷。控制和氘化标记实验以及 DFT 计算有力地支持了通过催化级联分子间和分子内氢化硅烷化机制形成硅杂环戊烷。独特的反应活性和选择性可归因于催化剂的大镧离子和ATE结构。
• SAKURAI, HIDEKI;SHOJI, MASATAKA;YAJIMA, MIKIO;HOSOMI, AKIRA, SYNTHESIS, BRD, 1984, N 7, 598-600
  作者：SAKURAI, HIDEKI、SHOJI, MASATAKA、YAJIMA, MIKIO、HOSOMI, AKIRA

  DOI：——

  日期：——
• Iron‐Catalyzed Allylic C(<i>sp</i>^<i>3</i>)−H Silylation: Spin‐Crossover‐Efficiency‐Determined Chemoselectivity
  作者：Peng He、Mu‐Han Guan、Meng‐Yang Hu、Yuan‐Jun Zhou、Ming‐Yao Huang、Shou‐Fei Zhu

  DOI：10.1002/anie.202402044

  日期：——

  The nuanced role of spin effects remains a critical gap in designing proficient open‐shell catalysts. This study elucidates an iron‐catalyzed allylic C(sp³)−H silylation/alkyne hydrosilylation reaction, in which the spin state of the open‐shell iron catalyst dictates the reaction kinetics and pathway. Specifically, spin crossover led to alkyne hydrosilylation, whereas spin conservation resulted in a novel allylic C(sp³)−H silylation reaction. This chemoselectivity, governed by the spin‐crossover efficiency, reveals an unexpected dimension in spin effects and a first in the realm of transition‐metal‐catalyzed in situ silylation of allylic C(sp³)−H bonds, which had been previously inhibited by the heightened reactivity of alkenes in hydrosilylation reactions. Furthermore, this spin crossover can either accelerate or hinder the reaction at different stages within a single catalytic reaction, a phenomenon scarcely documented. Moreover, we identify a substrate‐assisted C−H activation mechanism, a departure from known ligand‐assisted processes, offering a fresh perspective on C−H activation strategies.