methyl (E)-5-[tert-butyl(dimethyl)silyl]oxy-2-diazo-7-(4-methoxyphenyl)-3-oxohept-6-enoate | 1208449-79-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (E)-5-[tert-butyl(dimethyl)silyl]oxy-2-diazo-7-(4-methoxyphenyl)-3-oxohept-6-enoate
• CAS: 1208449-79-9
• 化学式: C₂₁H₃₀N₂O₅Si
• 分子量: 418.565
• InChiKey: JNZSBBWBHLYMRR-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-Diazo-3-oxo-butyric acid methyl ester 、 4-甲氧基肉桂醛 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 、 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到methyl (E)-5-[tert-butyl(dimethyl)silyl]oxy-2-diazo-7-(4-methoxyphenyl)-3-oxohept-6-enoate
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Functionalized α-Diazo-β-ketoalkanoates via Catalytic One-Pot Mukaiyama-Aldol Reactions

  摘要：

  Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce delta-siloxy-alpha-diazo-beta-ketoalkanoates in good yield, and delta-hydroxy-alpha-diazo-beta-ketoalkanoates are formed with high diastereoselectivity in reactions with alpha-diazo-beta-ketopentanoate promoted by dibutylboron triflate.

  DOI：

  10.1021/ol902872y

文献信息

• Stereoselective Synthesis of Highly Functionalized α-Diazo-β-ketoalkanoates via Catalytic One-Pot Mukaiyama-Aldol Reactions
  作者：Lei Zhou、Michael P. Doyle

  DOI：10.1021/ol902872y

  日期：2010.2.19

  Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce delta-siloxy-alpha-diazo-beta-ketoalkanoates in good yield, and delta-hydroxy-alpha-diazo-beta-ketoalkanoates are formed with high diastereoselectivity in reactions with alpha-diazo-beta-ketopentanoate promoted by dibutylboron triflate.