Methyl 5-[tert-butyl(dimethyl)silyl]oxy-2-diazo-5-(4-nitrophenyl)-3-oxopentanoate | 1020183-51-0

• 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: Methyl 5-[tert-butyl(dimethyl)silyl]oxy-2-diazo-5-(4-nitrophenyl)-3-oxopentanoate
• CAS: 1020183-51-0
• 化学式: C₁₈H₂₅N₃O₆Si
• 分子量: 407.498
• InChiKey: RXSWBXWFKUDMCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 5-[tert-butyl(dimethyl)silyl]oxy-2-diazo-5-(4-nitrophenyl)-3-oxopentanoate 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到Methyl 2-diazo-5-hydroxy-5-(4-nitrophenyl)-3-oxopentanoate
  参考文献：
  名称：

  An efficient methodology to substituted furans via oxidation of functionalized α-diazo-β-ketoacetates

  摘要：

  DMDO oxidation of functionalized alpha-diazo-beta-ketoacetates, formed by zinc triflate catalyzed Mukaiyama-aldol condensation of methyl diazoacetoacetate with aldehydes, occurred in quantitative yield to form dihydrofuranols that undergo acid catalyzed dehydration under mild conditions to generate 3-methoxy-furan-2-carboxylates in good yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.166
• 作为产物：
  描述：

  对硝基苯甲醛 、 methyl 3-tert-butyldimethylsilyloxy-2-diazobut-3-enoate 在 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到Methyl 5-[tert-butyl(dimethyl)silyl]oxy-2-diazo-5-(4-nitrophenyl)-3-oxopentanoate
  参考文献：
  名称：

  Construction of Highly Functionalized Diazoacetoacetates via Catalytic Mukaiyama−Michael Reactions

  摘要：

  Functionalized diazo acelloacetates are prepared by an efficient Mukaiyama-Michael reaction between methyl 3-(trialkylsilanoxy)-2-diazo-3-butenoate and alpha,beta-unsaturated enones. Vinyl ether and ketone derivatives are both accessible in good to excellent yield through this methodology. The mild Lewis acid zinc(II) triflate is the optimal catalyst, and its loading can be as low as 0.1 mol %. In addition, zinc triflate was also found to be a superior catalyst for the related Mukaiyama-aldol reaction.

  DOI：

  10.1021/ol800298n

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.