2-benz[a]anthraldehyde-1-ol | 918797-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-benz[a]anthraldehyde-1-ol
• 英文别名: 1-Hydroxytetraphene-2-carbaldehyde；1-hydroxybenzo[a]anthracene-2-carbaldehyde
• CAS: 918797-15-6
• 化学式: C₁₉H₁₂O₂
• 分子量: 272.303
• InChiKey: CTPHXLBSMHCGFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-氨基-2'-羟基-1,1'-联萘 、 2-benz[a]anthraldehyde-1-ol 以 乙醇 为溶剂， 反应 10.0h， 以81%的产率得到(S)-2-hydroxy-1,1'-binaphthyl-2'-imine-benz[a]anthracene-1-ol
  参考文献：
  名称：

  Synthesis and characterization of TiL 2 complexes with tridentate (ONO) ( S )-NOBIN Schiff-base ligands

  摘要：

  Tridentate (ONO) C-1-symmetric Schiff base ligands were synthesized by the condensation of (S)-2-amino-2'-hydroxy-1,1'-binaphthyalene with 4-hydroxy-3-phenanthrenecarboxaldehyde or 1-hydroxybenz[a]anthracene-2-carboxaldehyde. C-2-symmetric titanium(IV) Schiff base complexes, TiL2, were synthesized and characterized with these ligands. The complex with the benz[a]anthryl unit crystallizes in a facial coordination mode, OC-6-1'3'-C, whereas complex with phenanthryl unit crystallizes in a meridional mode, OC-6-22'-A. A comparison between the complexes and the ligands were done in solution using circular dichroism spectroscopy. Preliminary catalytic studies showed that these complexes can catalyze asymmetric carbonyl-ene addition reactions of 2-methoxypropene with aromatic aldehydes with moderate selectivity. The ligands and complexes were characterized by NMR, HRMS, single crystal X-ray diffraction and CD spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.07.001

文献信息

• Synthesis and characterization of TiL 2 complexes with tridentate (ONO) ( S )-NOBIN Schiff-base ligands
  作者：Sanmitra Barman、John Desper、Christopher J. Levy

  DOI：10.1016/j.poly.2014.07.001

  日期：2014.12

  Tridentate (ONO) C-1-symmetric Schiff base ligands were synthesized by the condensation of (S)-2-amino-2'-hydroxy-1,1'-binaphthyalene with 4-hydroxy-3-phenanthrenecarboxaldehyde or 1-hydroxybenz[a]anthracene-2-carboxaldehyde. C-2-symmetric titanium(IV) Schiff base complexes, TiL2, were synthesized and characterized with these ligands. The complex with the benz[a]anthryl unit crystallizes in a facial coordination mode, OC-6-1'3'-C, whereas complex with phenanthryl unit crystallizes in a meridional mode, OC-6-22'-A. A comparison between the complexes and the ligands were done in solution using circular dichroism spectroscopy. Preliminary catalytic studies showed that these complexes can catalyze asymmetric carbonyl-ene addition reactions of 2-methoxypropene with aromatic aldehydes with moderate selectivity. The ligands and complexes were characterized by NMR, HRMS, single crystal X-ray diffraction and CD spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.