ethyl 3(R)-azido-2(R)-hydroxy-2-methyl-4-oxo-4-phenylbutanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3(R)-azido-2(R)-hydroxy-2-methyl-4-oxo-4-phenylbutanoate
• 英文别名: ethyl (2R,3R)-3-azido-2-hydroxy-2-methyl-4-oxo-4-phenylbutanoate
• 化学式: C₁₃H₁₅N₃O₄
• 分子量: 277.28
• InChiKey: MZCUJBIMWBXYPU-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙酮酸乙酯 、 2-azido-1-phenylethan-1-one 在 氢化奎宁(蒽醌-1,4-二基)二醚 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以30%的产率得到
  参考文献：
  名称：

  Asymmetric aldol addition of α-azido ketones to ethyl pyruvate mediated by a cinchona-based bifunctional urea catalyst

  摘要：

  The first asymmetric synthesis of ethyl 4-aryl-3-azido-2-hydroxy-2-methyl-4-oxobutanoates via a cinchona organocatalyst induced aldol addition of alpha-azido ketones to ethyl pyruvate has been developed. The coupling reaction under optimized conditions was carried out to furnish tetrafunctionalized synthons with enantioselectivities of up to 91:9 and enriched diastereoselectivities of up to 95:5 (syn:anti). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.018

文献信息

• Asymmetric aldol addition of α-azido ketones to ethyl pyruvate mediated by a cinchona-based bifunctional urea catalyst
  作者：Seda Okumuş、Cihangir Tanyeli、Ayhan S. Demir

  DOI：10.1016/j.tetlet.2014.06.018

  日期：2014.7

  The first asymmetric synthesis of ethyl 4-aryl-3-azido-2-hydroxy-2-methyl-4-oxobutanoates via a cinchona organocatalyst induced aldol addition of alpha-azido ketones to ethyl pyruvate has been developed. The coupling reaction under optimized conditions was carried out to furnish tetrafunctionalized synthons with enantioselectivities of up to 91:9 and enriched diastereoselectivities of up to 95:5 (syn:anti). (C) 2014 Elsevier Ltd. All rights reserved.