(E)-di-tert-butyl 2-(4-hydroxy-2-methylbenzyl)-2-(4-[(methoxycarbonyl)oxy]but-2-en-1-yl)malonate | 1254472-77-9

• 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: (E)-di-tert-butyl 2-(4-hydroxy-2-methylbenzyl)-2-(4-[(methoxycarbonyl)oxy]but-2-en-1-yl)malonate
• 英文别名: ditert-butyl 2-[(4-hydroxy-2-methylphenyl)methyl]-2-[(E)-4-methoxycarbonyloxybut-2-enyl]propanedioate
• CAS: 1254472-77-9
• 化学式: C₂₅H₃₆O₈
• 分子量: 464.556
• InChiKey: KNQWAPTYWCSCJE-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-di-tert-butyl 2-(4-hydroxy-2-methylbenzyl)-2-(4-[(methoxycarbonyl)oxy]but-2-en-1-yl)malonate 在 (R,R)-ANDEN-phenyl Trost Ligand 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 di-tert-butyl 6-methyl-8-oxo-4-vinylspiro[4.5]deca-6,9-diene-2,2-dicarboxylate 、 di-tert-butyl 6-methyl-8-oxo-4-vinylspiro[4.5]deca-6,9-diene-2,2-dicarboxylate 、 di-tert-butyl 6-methyl-8-oxo-4-vinylspiro[4.5]deca-6,9-diene-2,2-dicarboxylate
  参考文献：
  名称：

  Enantioselective construction of all-carbon quaternary spirocenters through a Pd-catalyzed asymmetric intramolecular ipso-Friedel–Crafts allylic alkylation of phenols

  摘要：

  A novel catalytic asymmetric synthetic method for making spirocyclohexadienones with an all-carbon quaternary spirocenter was developed based on the Pd-catalyzed intramolecular ipso-Friedel-Crafts allylic alkylation of phenols. When 5 mol % of the Pd catalyst and 12 mol % of (-)-9-NapBN (-)-3e were used, the spirocyclic adduct was obtained with up to 93% ee, albeit with low chemical yield. On the other hand, when using 6 mol% of the Trost ligand (R,R)-3k, the spirocyclic adducts were obtained in good yields with up to 89% ee (diastereoselectivity = 9.2:1). (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.026