1-(β-chloroethyl)-4-t-Bu-imidazole | 1068442-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(β-chloroethyl)-4-t-Bu-imidazole
• 英文别名: 4-Tert-butyl-1-(2-chloroethyl)imidazole
• CAS: 1068442-27-2
• 化学式: C₉H₁₅ClN₂
• 分子量: 186.684
• InChiKey: HEBQBOQYWKHTIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(β-chloroethyl)-4-t-Bu-imidazole 在 氢氧化钾 、 对苯二酚 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 以86%的产率得到4-tert-butyl-1-vinyl-1H-imidazole
  参考文献：
  名称：

  Imidazol-2-yl Complexes of Cp*Ir as Bifunctional Ambident Reactants

  摘要：

  Loss of chloride ion from imidazol-2-yl complex 4a activates the H-H bond of dihydrogen or the C-H bond of actelyene, forming and Ir(III) N-heterocyclic (NHC) complex (3b or 9). Deprotonation of Ir(III) hydride 4b gives one new species, formulated as IR(I) carbene complex 5. Protonation or alkylation of 5 occurs at the metal, returning the IR(III) core of 6a,b. Deprotonation of cationic NHC complex 3a gives neutral imidazol-2-yl analogue 4a; as seen by X-ray diffraction, the Ir-C bond in 3a is shorter than that in 4a. These and other comparisons and interconversions of NHC complexes with an NH function and related imidazol-2-yl species expand the potential of NHC complexes by showing their bifunctional character.

  DOI：

  10.1021/ja804713u
• 作为产物：
  描述：

  5-叔丁基-1H-咪唑 、 1,2-二氯乙烷 在 氢氧化钾 、 四丁基溴化铵 、 potassium carbonate 作用下， 反应 4.0h， 以67%的产率得到1-(β-chloroethyl)-4-t-Bu-imidazole
  参考文献：
  名称：

  Imidazol-2-yl Complexes of Cp*Ir as Bifunctional Ambident Reactants

  摘要：

  Loss of chloride ion from imidazol-2-yl complex 4a activates the H-H bond of dihydrogen or the C-H bond of actelyene, forming and Ir(III) N-heterocyclic (NHC) complex (3b or 9). Deprotonation of Ir(III) hydride 4b gives one new species, formulated as IR(I) carbene complex 5. Protonation or alkylation of 5 occurs at the metal, returning the IR(III) core of 6a,b. Deprotonation of cationic NHC complex 3a gives neutral imidazol-2-yl analogue 4a; as seen by X-ray diffraction, the Ir-C bond in 3a is shorter than that in 4a. These and other comparisons and interconversions of NHC complexes with an NH function and related imidazol-2-yl species expand the potential of NHC complexes by showing their bifunctional character.

  DOI：

  10.1021/ja804713u