Di-tert-butylphenylsilanol | 151340-95-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Di-tert-butylphenylsilanol
• 英文别名: Ditert-butyl-hydroxy-phenylsilane
• CAS: 151340-95-3
• 化学式: C₁₄H₂₄OSi
• 分子量: 236.429
• InChiKey: YAOMQFUAGYZCIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  二氧化碳 、 Di-tert-butylphenylsilanol 在 三甲基硅烷化重氮甲烷 作用下， 生成 1,1-Di-tert-butyl-1H-benzo[c][1,2]oxasilol-3-one 、 3-(Di-tert-butyl-hydroxy-silanyl)-benzoic acid methyl ester 、 4-(Di-tert-butyl-hydroxy-silanyl)-benzoic acid methyl ester
  参考文献：
  名称：

  Silanol reactivity: evaluation of silanolate as a metalation-directing group

  摘要：

  Alkali metal salts of dimethylarylsilanol and di-tert-butylphenylsilanol were treated with organometallic reagents to determine the viability of silanolates as ortho-metalation-directing groups. When dimethylphenylsilanol was treated with an excess of n-butyllithium, metalation was not observed. Heating these reactions led to substitution of the methyl and phenyl groups on silicon by n-butyl groups. When a m-methoxy group was present, metalation of the aromatic ring was observed between the two substituents. The more hindered di-tert-butylphenylsilanol was inert to excess n-butyllithium, but treatment of the potassium salt of this silanol with n-butyllithium results in metalation largely at the meta and para positions, with only traces of ortho products. Calculated deprotonation enthalpies of arylsilanes using AM1 can explain some of the observed acidities from this study as well as observations made in a related study of arylsilane metalation by Schlosser et al.

  DOI：

  10.1021/jo00075a026
• 作为产物：
  描述：

  二-叔丁基二氟硅烷 、 苯基锂 在 sodium hydroxide 作用下， 生成 Di-tert-butylphenylsilanol
  参考文献：
  名称：

  Silanol reactivity: evaluation of silanolate as a metalation-directing group

  摘要：

  Alkali metal salts of dimethylarylsilanol and di-tert-butylphenylsilanol were treated with organometallic reagents to determine the viability of silanolates as ortho-metalation-directing groups. When dimethylphenylsilanol was treated with an excess of n-butyllithium, metalation was not observed. Heating these reactions led to substitution of the methyl and phenyl groups on silicon by n-butyl groups. When a m-methoxy group was present, metalation of the aromatic ring was observed between the two substituents. The more hindered di-tert-butylphenylsilanol was inert to excess n-butyllithium, but treatment of the potassium salt of this silanol with n-butyllithium results in metalation largely at the meta and para positions, with only traces of ortho products. Calculated deprotonation enthalpies of arylsilanes using AM1 can explain some of the observed acidities from this study as well as observations made in a related study of arylsilane metalation by Schlosser et al.

  DOI：

  10.1021/jo00075a026

文献信息

• Silanol reactivity: evaluation of silanolate as a metalation-directing group
  作者：Scott M. Sieburth、Louis Fensterbank

  DOI：10.1021/jo00075a026

  日期：1993.11

  Alkali metal salts of dimethylarylsilanol and di-tert-butylphenylsilanol were treated with organometallic reagents to determine the viability of silanolates as ortho-metalation-directing groups. When dimethylphenylsilanol was treated with an excess of n-butyllithium, metalation was not observed. Heating these reactions led to substitution of the methyl and phenyl groups on silicon by n-butyl groups. When a m-methoxy group was present, metalation of the aromatic ring was observed between the two substituents. The more hindered di-tert-butylphenylsilanol was inert to excess n-butyllithium, but treatment of the potassium salt of this silanol with n-butyllithium results in metalation largely at the meta and para positions, with only traces of ortho products. Calculated deprotonation enthalpies of arylsilanes using AM1 can explain some of the observed acidities from this study as well as observations made in a related study of arylsilane metalation by Schlosser et al.