tert-butyl 9,10-dihydro-9-anthroate | 89302-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: tert-butyl 9,10-dihydro-9-anthroate
• 英文别名: tert-butyl 9,10-dihydroanthracene-10-carboxylate；Tert-butyl 9,10-dihydroanthracene-9-carboxylate
• CAS: 89302-39-6
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: JROFACYESGEFCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  叔-丁基蒽-9-羧酸酯 在 C₂₄H₃₂N₈Ni⁽²⁺⁾*2I^(1-) 、 sodium amalgam 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以85%的产率得到tert-butyl 9,10-dihydro-9-anthroate
  参考文献：
  名称：

  Reductions of Challenging Organic Substrates by a Nickel Complex of a Noninnocent Crown Carbene Ligand

  摘要：

  The first crown-tetracarbene complex of Ni(II) has been prepared, and its crystal structure determined. The complex can be reduced by Na/Hg, with an uptake of two electrons. The reduced complex reductively cleaves arenesulfonamides, including those derived from secondary aliphatic amines, and effects Birch reduction of anthracenes as well as reductive cleavage of stilbene oxides. Computational studies show that the orbital that receives electrons upon reduction of the complex 2 is predominantly based on the crown carbene ligand and also that the HOMO of the parent complex 2 is based on the ligand.

  DOI：

  10.1021/ja107703n

文献信息

• Metal-ammonia ring reduction of aromatic carboxylic acid esters
  作者：Peter W. Rabideau、Donna M. Wetzel、D. Michael Young

  DOI：10.1021/jo00183a014

  日期：1984.5
• RABIDEAU, P. W.;WETZEL, D. M.;YOUNG, D. M., J. ORG. CHEM., 1984, 49, N 9, 1544-1549
  作者：RABIDEAU, P. W.、WETZEL, D. M.、YOUNG, D. M.

  DOI：——

  日期：——
• Reductions of Challenging Organic Substrates by a Nickel Complex of a Noninnocent Crown Carbene Ligand
  作者：Neil J. Findlay、Stuart R. Park、Franziska Schoenebeck、Elise Cahard、Sheng-ze Zhou、Leonard E. A. Berlouis、Mark D. Spicer、Tell Tuttle、John A. Murphy

  DOI：10.1021/ja107703n

  日期：2010.11.10

  The first crown-tetracarbene complex of Ni(II) has been prepared, and its crystal structure determined. The complex can be reduced by Na/Hg, with an uptake of two electrons. The reduced complex reductively cleaves arenesulfonamides, including those derived from secondary aliphatic amines, and effects Birch reduction of anthracenes as well as reductive cleavage of stilbene oxides. Computational studies show that the orbital that receives electrons upon reduction of the complex 2 is predominantly based on the crown carbene ligand and also that the HOMO of the parent complex 2 is based on the ligand.