(R)-5-ethoxy-4-(1-(naphthalen-1-yl)-2-nitroethyl)furan-3(2H)-one | 1384457-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-5-ethoxy-4-(1-(naphthalen-1-yl)-2-nitroethyl)furan-3(2H)-one
• 英文别名: 5-ethoxy-4-[(1R)-1-naphthalen-1-yl-2-nitroethyl]furan-3-one
• CAS: 1384457-03-7
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: WRQCRISXNNFYNB-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  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-(1-(naphthalen-1-yl)-2-nitroethyl)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