2-tert-butyl 1-ethyl naphthalene-1,2-dicarboxylate | 1209469-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-tert-butyl 1-ethyl naphthalene-1,2-dicarboxylate
• 英文别名: 2-O-tert-butyl 1-O-ethyl naphthalene-1,2-dicarboxylate
• CAS: 1209469-78-2
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: LLIBAKMHNKTSMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1-萘甲酸乙酯 在 bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 以69%的产率得到2-tert-butyl 1-ethyl naphthalene-1,2-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