4-(tert-butoxycarbonylmethylamino)cyclohexylzinc iodide | 1537869-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(tert-butoxycarbonylmethylamino)cyclohexylzinc iodide
• CAS: 1537869-26-3
• 化学式: C₁₂H₂₂INO₂Zn
• 分子量: 404.607
• InChiKey: CWWSZBOCNPMAEA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-碘苯甲酸甲酯 、 4-(tert-butoxycarbonylmethylamino)cyclohexylzinc iodide 在 Ruphos 、 lithium chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 N-乙基-2-吡咯烷酮 作用下， 以 四氢呋喃 为溶剂， 反应 48.17h， 以78%的产率得到methyl 4-(trans-4-(tert-butoxycarbonylmethylamino)cyclohexyl) benzoate
  参考文献：
  名称：

  Diastereoconvergent Negishi Cross-Coupling Using Functionalized Cyclohexylzinc Reagents

  摘要：

  Highly diastereoselective Pd-catalyzed cross-coupling reactions of functionalized 2-, 3-, and 4-substituted cyclohexylzinc reagents with aryl, heteroaryl, and alkenyl iodides have been performed under mild conditions. The use of Ruphos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl) as a ligand as well as LiCl and N-ethylpyrrolidone (NEP) as additives leads to especially high diastereoselectivities and displays good functional group tolerance. The stereoselectivity can be explained by assuming that the intermediate palladium moiety occupies an equatorial position of the cyclohexyl ring.

  DOI：

  10.1021/ol403673e
• 作为产物：
  描述：

  4-(N-Boc-N-甲氨基)环己醇 在 N-甲基咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-(tert-butoxycarbonylmethylamino)cyclohexylzinc iodide
  参考文献：
  名称：

  Diastereoconvergent Negishi Cross-Coupling Using Functionalized Cyclohexylzinc Reagents

  摘要：

  Highly diastereoselective Pd-catalyzed cross-coupling reactions of functionalized 2-, 3-, and 4-substituted cyclohexylzinc reagents with aryl, heteroaryl, and alkenyl iodides have been performed under mild conditions. The use of Ruphos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl) as a ligand as well as LiCl and N-ethylpyrrolidone (NEP) as additives leads to especially high diastereoselectivities and displays good functional group tolerance. The stereoselectivity can be explained by assuming that the intermediate palladium moiety occupies an equatorial position of the cyclohexyl ring.

  DOI：

  10.1021/ol403673e