di-tert-butyl 4'-cyanobiphenyl-2,4-dicarboxylate | 1209469-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: di-tert-butyl 4'-cyanobiphenyl-2,4-dicarboxylate
• CAS: 1209469-77-1
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: JUABRSMTGCWZAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  76.39
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-溴苯腈 、 间苯二甲酸二叔丁酯 在 bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex 、 zinc(II) chloride 、 palladium diacetate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以75%的产率得到di-tert-butyl 4'-cyanobiphenyl-2,4-dicarboxylate
  参考文献：
  名称：

  Scaleable Preparation of Functionalized Organometallics via Directed Ortho Metalation Using Mg- and Zn-Amide Bases

  摘要：

  A range of aryl and heteroaryl organometallics are efficiently prepared in THF via directed ortho metalation by using the previously reported amide bases tmpMgCl center dot LiCl (tmp = 2,2,6,6-tetramethylpiperidyl), tmp(2)Mg center dot 2LiCl and tmp(2)Zn center dot 2MgCl(2)center dot 2LiCl. These metalation reactions are carried out at 80-100 mmol scale. The unsaturated organometallic compounds undergo smooth reactions with various electrophiles, e.g. additions to carbonyl groups, Pd-catalyzed cross-coupling reactions or Cu-catalyzed acylations. In all cases, the metalation rates have been compared with corresponding small-scale reactions (1-2 mmol). Moreover, a procedure for the recovery of the valuable tmp-H from the aqueous layer is reported.

  DOI：

  10.1021/op9002888