6-chloro-2-(3,3-dimethyl-butyl)-1H-benzimidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-chloro-2-(3,3-dimethyl-butyl)-1H-benzimidazole
• 英文别名: 6-chloro-2-(3,3-dimethylbutyl)-1H-benzimidazole
• 化学式: C₁₃H₁₇ClN₂
• 分子量: 236.744
• InChiKey: RIATVLLRJISYJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3-二甲基-1-丁烯 、 5-氯苯并咪唑 在 [RhCl(coe)2]2 tricyclohexylphosphonium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以93%的产率得到6-chloro-2-(3,3-dimethyl-butyl)-1H-benzimidazole
  参考文献：
  名称：

  Intermolecular Coupling of Alkenes to Heterocycles via C−H Bond Activation

  摘要：

  The intermolecular coupling of unactivated alkenes to a range of heterocycles using a Rh(I) catalyst was investigated. A variety of functional groups were incorporated into the alkene, including esters, nitriles, acetals, and phthalimide. Furthermore, the heterocycle tolerated substitution with both electron-rich and electron-deficient groups. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions. An extensive optimization of additives was performed, and HCI.PCY3 (Cy = cyclohexyl) and HCI-P-t-Bu2Et were in general found to be the best additives for the reaction.

  DOI：

  10.1021/jo048666p

文献信息

• Intermolecular Coupling of Alkenes to Heterocycles via C−H Bond Activation
  作者：Kian L. Tan、Steve Park、Jonathan A. Ellman、Robert G. Bergman

  DOI：10.1021/jo048666p

  日期：2004.10.1

  The intermolecular coupling of unactivated alkenes to a range of heterocycles using a Rh(I) catalyst was investigated. A variety of functional groups were incorporated into the alkene, including esters, nitriles, acetals, and phthalimide. Furthermore, the heterocycle tolerated substitution with both electron-rich and electron-deficient groups. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions. An extensive optimization of additives was performed, and HCI.PCY3 (Cy = cyclohexyl) and HCI-P-t-Bu2Et were in general found to be the best additives for the reaction.