ethyl 4-chloro-2-((S)-2-nitro-1-phenylethyl)-3-oxobutanoate | 1384456-74-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-chloro-2-((S)-2-nitro-1-phenylethyl)-3-oxobutanoate
• CAS: 1384456-74-9
• 化学式: C₁₄H₁₆ClNO₅
• 分子量: 313.738
• InChiKey: BSNGTNXHWBOPQW-JTDNENJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-chloro-2-((S)-2-nitro-1-phenylethyl)-3-oxobutanoate 在 lithium acetate 、 铜色树碱 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 (R)-5-ethoxy-4-(2-nitro-1-phenylethyl)furan-3(2H)-one
  参考文献：
  名称：

  Synthesis of chiral tetronic acid derivatives via organocatalytic conjugate addition of ethyl 4-chloro-3-oxobutanoate to nitroalkenes

  摘要：

  Asymmetric conjugate addition of ethyl 4-chloro-3-oxobutanoate to nitroalkenes and subsequent intramolecular cyclization had been developed. This one-pot reaction provided tetronic acid derivatives in good yields and with excellent enantioselectivities. 6'-Demethyl quinine was found to be the best catalyst for the conjugate addition and AcOLi was identified as the best base for the intramolecular cyclization. Various beta-aryl, heteroaryl, and alkyl nitroalkenes are generally applicable in the reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.082
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 β-硝基苯乙烯 在 铜色树碱 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 ethyl 4-chloro-2-((S)-2-nitro-1-phenylethyl)-3-oxobutanoate
  参考文献：
  名称：

  Synthesis of chiral tetronic acid derivatives via organocatalytic conjugate addition of ethyl 4-chloro-3-oxobutanoate to nitroalkenes

  摘要：

  Asymmetric conjugate addition of ethyl 4-chloro-3-oxobutanoate to nitroalkenes and subsequent intramolecular cyclization had been developed. This one-pot reaction provided tetronic acid derivatives in good yields and with excellent enantioselectivities. 6'-Demethyl quinine was found to be the best catalyst for the conjugate addition and AcOLi was identified as the best base for the intramolecular cyclization. Various beta-aryl, heteroaryl, and alkyl nitroalkenes are generally applicable in the reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.082