3-tert-butyl-2-hydroxy-5-(p-vinylbenzyloxy)benzaldehyde | 192803-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-tert-butyl-2-hydroxy-5-(p-vinylbenzyloxy)benzaldehyde
• 英文别名: 5-(4-vinylbenzyloxy)-3-tert-butyl salicylaldehyde；3-(1,1-Dimethylethyl)-5-[(4-ethenylphenyl)methoxy]-2-hydroxybenzaldehyde；3-tert-butyl-5-[(4-ethenylphenyl)methoxy]-2-hydroxybenzaldehyde
• CAS: 192803-38-6
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: UHFYPAFVXJUQNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  L-叔亮氨醇 、 3-tert-butyl-2-hydroxy-5-(p-vinylbenzyloxy)benzaldehyde 以 乙醇 为溶剂， 反应 6.0h， 以70%的产率得到(S)-2-[N-3-tert-butyl-5-(p-vinylbenzyloxy)salicyden]amino-3,3-dimethyl-1-butanol
  参考文献：
  名称：

  Enantioselective sulfoxidation catalyzed by polymer-supported chiral Schiff base–VO(acac)2 complexes

  摘要：

  The preparation of a series of polymer supported chiral Schiff bases derived from salicylic aldehydes and optically active amino alcohols is reported. These heterogeneous ligands have been complexed with VO(acac)(2) and employed to catalyze the enantioselective oxidation of sulfides to sulfoxides with hydrogen peroxide as an environmentally acceptable oxidant. The procedure affords the sulfoxides in good yield and selectivity and with ee values comparable to those obtained with the homogeneous counterparts. The catalyst can be used for at least four cycles without any significant decrease in both efficiency or enantioselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.041
• 作为产物：
  描述：

  4-vinylbenzyl iodide 、 3-叔丁基-2,5-二羟基苯甲醛 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以73%的产率得到3-tert-butyl-2-hydroxy-5-(p-vinylbenzyloxy)benzaldehyde
  参考文献：
  名称：

  Enantioselective sulfoxidation catalyzed by polymer-supported chiral Schiff base–VO(acac)2 complexes

  摘要：

  The preparation of a series of polymer supported chiral Schiff bases derived from salicylic aldehydes and optically active amino alcohols is reported. These heterogeneous ligands have been complexed with VO(acac)(2) and employed to catalyze the enantioselective oxidation of sulfides to sulfoxides with hydrogen peroxide as an environmentally acceptable oxidant. The procedure affords the sulfoxides in good yield and selectivity and with ee values comparable to those obtained with the homogeneous counterparts. The catalyst can be used for at least four cycles without any significant decrease in both efficiency or enantioselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.041

文献信息

• New chloramphenicol Schiff base ligands for the titanium-mediated asymmetric aldol reaction of α,β-unsaturated aldehydes with diketene: a short synthesis of atorvastatin calcium
  作者：Haifeng Wang、Linjie Yan、Fangjun Xiong、Yan Wu、Fener Chen

  DOI：10.1039/c6ra15304f

  日期：——

  Several novel chiral Schiff base ligands were prepared from a commercially available chloramphenicol base and applied to the titanium-mediated asymmetric aldol reaction of diketene with various α,β-unsaturated aldehydes. This reaction proceeded in good yield with high enantioselectivity. The synthetic utility of this methodology was demonstrated in the short synthesis of atorvastatin calcium.

  从可商购的氯霉素碱制备了几种新颖的手性席夫碱配体，并将其应用于双烯酮与各种α，β-不饱和醛的钛介导的不对称醛醇缩合反应。该反应以高收率和高对映选择性进行。这种方法的合成效用在阿托伐他汀钙的短时合成中得到了证明。
• Enantioselective epoxidation of olefins catalyzed by polymer-bound optically active Mn(III)-salen complex
  作者：Binod B. De、Braj B. Lohray、Swaminathan Sivaram、Pradeep K. Dhal

  DOI：10.1016/0957-4166(95)00275-t

  日期：1995.9