(α,α-dimethylbenzyl)dimethylsilanol | 144467-97-0

• 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: (α,α-dimethylbenzyl)dimethylsilanol
• 英文别名: (1-phenyl-1-methylethyl)dimethylsilanol；Silanol, dimethyl(1-methyl-1-phenylethyl)-；hydroxy-dimethyl-(2-phenylpropan-2-yl)silane
• CAS: 144467-97-0
• 化学式: C₁₁H₁₈OSi
• 分子量: 194.349
• InChiKey: QDBMRBGBZWPJOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (α,α-dimethylbenzyl)dimethylsilanol 在 N-甲基吗啉 、 硝酸铵 、 草酰氯 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 三氟乙酸酐 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.33h， 生成 N-(9-fluorenylmethoxycarbonyl)-O-[(4-amino-α,α-dimethylbenzyl)dimethylsilyl]-L-serine allyl ester
  参考文献：
  名称：

  A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis

  摘要：

  In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00649-3
• 作为产物：
  描述：

  phenyl(1-hydroxy-1-methylethyl)dimethylsilane 在 二氯乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到(α,α-dimethylbenzyl)dimethylsilanol
  参考文献：
  名称：

  Rearrangements of organosilicon compounds using organoaluminum reagents. Conversion of phenyl- and alkenyl(chloromethyl)silanes to benzyl- and allylsilanes

  摘要：

  Various (chloromethyl)silanes undergo Wagner-Meerwein-type rearrangements using a catalytic amount of EtAlCl2 in dichloromethane. The resulting chlorosilanes have been converted to alkyl(or aryl)silanes with RMgX and/or to fluorosilanes with NH4BF2. In this way phenyl-, alkenyl-, and allyl(chloromethyl)silanes were converted to benzyl-, allyl-, and homoallylsilanes, respectively. Attempted rearrangements of methyl-, alkynyl-, and furyl(chloromethyl)silanes under these conditions were not successful.

  DOI：

  10.1021/jo00050a034

文献信息

• Rearrangements of organosilicon compounds using organoaluminum reagents. Conversion of phenyl- and alkenyl(chloromethyl)silanes to benzyl- and allylsilanes
  作者：Paul F. Hudrlik、Yousef M. Abdallah、Ashok K. Kulkarni、Anne M. Hudrlik

  DOI：10.1021/jo00050a034

  日期：1992.11

  Various (chloromethyl)silanes undergo Wagner-Meerwein-type rearrangements using a catalytic amount of EtAlCl2 in dichloromethane. The resulting chlorosilanes have been converted to alkyl(or aryl)silanes with RMgX and/or to fluorosilanes with NH4BF2. In this way phenyl-, alkenyl-, and allyl(chloromethyl)silanes were converted to benzyl-, allyl-, and homoallylsilanes, respectively. Attempted rearrangements of methyl-, alkynyl-, and furyl(chloromethyl)silanes under these conditions were not successful.
• A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis
  作者：Kazuhiko Nakamura、Akira Ishii、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0040-4020(99)00649-3

  日期：1999.9

  In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.