2-[(4-chlorophenyl)-(trimethylsiloxy)-methyl]-malonic acid di-tert-butyl ester | 1204142-50-6

• 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: 2-[(4-chlorophenyl)-(trimethylsiloxy)-methyl]-malonic acid di-tert-butyl ester
• 英文别名: Ditert-butyl 2-[(4-chlorophenyl)-trimethylsilyloxymethyl]propanedioate；ditert-butyl 2-[(4-chlorophenyl)-trimethylsilyloxymethyl]propanedioate
• CAS: 1204142-50-6
• 化学式: C₂₁H₃₃ClO₅Si
• 分子量: 429.029
• InChiKey: WMMQNPZFCQUALL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 2-[(4-chlorophenyl)-hydroxymethyl]-malonic acid di-tert-butyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-[(4-chlorophenyl)-(trimethylsiloxy)-methyl]-malonic acid di-tert-butyl ester
  参考文献：
  名称：

  Synthesis of β-hydroxymalonates: the direct aldol addition of malonates to aldehydes in the presence of SiCl4 and i-Pr2EtN

  摘要：

  The direct aldol addition of malonates to aromatic, hetero-aromatic and unsaturated aldehydes leading to beta-hydroxymalonates is described. The stability of these products, the trimethyl silyl protection of the hydroxyl group as well as the role of both SiCl4 and i-Pr2EtN in attaining the final products are also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.057

文献信息

• Trimethylchlorosilane and Silicon Tetrachloride in Two Novel Methodologies for the Efficient and Mild Aldol Addition of β-Keto Esters and Malonates to Aldehydes
  作者：Antonio Massa、Ada Roscigno、Paolo De Caprariis、Rosanna Filosa、Antonia Di Mola

  DOI：10.1002/adsc.201000573

  日期：2010.12.17

  mild aldol additions of β-keto esters and malonates to aldehydes are described using two novel protocols in the presence of silicon tetrachloride and trimethylchlorosilane, respectively. Scope and limitations of the methods have been discussed. Moreover the stability of the obtained products, trimethylsilyl protection of the hydroxy group, as well as the role of both silicon tetrachloride and trimethylchlorosilane

  描述了分别在四氯化硅和三甲基氯硅烷存在下使用两种新颖的方法将β-酮酸酯和丙二酸酯高效和温和地添加到醛中的方法。已经讨论了方法的范围和局限性。此外，还分析了所得产物的稳定性，羟基的三甲基甲硅烷基保护以及四氯化硅和三甲基氯硅烷在获得最终产物中的作用。