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1-[4-(tert-butyldimethylsilyloxy)benzyl]-2-[4-(tertbutyldimethylsilyloxy)phenyl]-1H-benzimidazole | 1407156-96-0

中文名称
——
中文别名
——
英文名称
1-[4-(tert-butyldimethylsilyloxy)benzyl]-2-[4-(tertbutyldimethylsilyloxy)phenyl]-1H-benzimidazole
英文别名
Tert-butyl-[4-[[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]benzimidazol-1-yl]methyl]phenoxy]-dimethylsilane;tert-butyl-[4-[[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]benzimidazol-1-yl]methyl]phenoxy]-dimethylsilane
1-[4-(tert-butyldimethylsilyloxy)benzyl]-2-[4-(tertbutyldimethylsilyloxy)phenyl]-1H-benzimidazole化学式
CAS
1407156-96-0
化学式
C32H44N2O2Si2
mdl
——
分子量
544.885
InChiKey
BTAWZTYDYHZYNV-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    9.52
  • 重原子数:
    38
  • 可旋转键数:
    9
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.41
  • 拓扑面积:
    36.3
  • 氢给体数:
    0
  • 氢受体数:
    3

反应信息

  • 作为产物:
    描述:
    4-[(叔-丁基二甲基甲硅烷)氧代]苯甲醛邻苯二胺2,2,2-三氟乙醇 为溶剂, 反应 0.5h, 以95%的产率得到1-[4-(tert-butyldimethylsilyloxy)benzyl]-2-[4-(tertbutyldimethylsilyloxy)phenyl]-1H-benzimidazole
    参考文献:
    名称:
    Hydrogen-Bond-Driven Electrophilic Activation for Selectivity Control: Scope and Limitations of Fluorous Alcohol-Promoted Selective Formation of 1,2-Disubstituted Benzimidazoles and Mechanistic Insight for Rationale of Selectivity
    摘要:
    Hydrogen-bond-driven electrophilic activation for selectivity control during competitive formation of 1,2-disubstituted and 2-substituted benzimidazoles from o-phenylenediamine and aldehydes is reported. The fluorous alcohols trifluoroethanol and hexafluoro-2-propanol efficiently promote the cyclocondensation of o-phenylenediamine with aldehydes to afford selectively the 1,2-disubstituted benzimidazoles at rt in short times. A mechanistic insight is invoked by NMR, mass spectrometry, and chemical studies to rationalize the selectivity. The ability of the fluorous alcohols in promoting the reaction and controlling the selectivity can be envisaged from their better hydrogen bond donor (HBD) abilities compared to that of the other organic solvents as well as of water. Due to the better HBD values, the fluorous alcohols efficiently promote the initial bisimine formation by electrophilic activation of the aldehyde carbonyl. Subsequently the hydrogen-bond-mediated activation of the in situ-formed bisimine triggers the rearrangement via 1,3-hydride shift to form the 1,2-disubstituted benzimidazoles.
    DOI:
    10.1021/jo301793z
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