(R)-5-ethoxy-4-(2-nitro-1-phenylethyl)furan-3(2H)-one | 1361938-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (R)-5-ethoxy-4-(2-nitro-1-phenylethyl)furan-3(2H)-one
• 英文别名: 5-ethoxy-4-[(1R)-2-nitro-1-phenylethyl]furan-3-one
• CAS: 1361938-46-6
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: MJQBPRLZROPENU-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-5-ethoxy-4-(2-nitro-1-phenylethyl)furan-3(2H)-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以95%的产率得到
  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-溴乙酰乙酸乙酯 在 lithium acetate 、 铜色树碱 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 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

文献信息

• From the Feist-Bénary Reaction to Organocatalytic Domino Michael-Alkylation Reactions: Asymmetric Synthesis of 3(2 H)-Furanones
  作者：Xiaowei Dou、Xiaoyu Han、Yixin Lu

  DOI：10.1002/chem.201102796

  日期：2012.1.2

  It all adds up! A modified Feist–Bénary reaction employing a domino Michael–alkylation sequence was designed for the enantioselective synthesis of 3(2 H)‐furanones. L‐Threonine‐derived tertiary amine/thiourea catalysts were prepared for the first time; such catalysts promoted the designed domino Michael–alkylation reactions in a highly enantioselective manner (see scheme).

  这一切加起来！使用多米诺骨牌迈克尔-烷基化序列的改进的Feist-Bénary反应设计用于3（2 H）-呋喃酮的对映选择性合成 。首次制备了L-苏氨酸衍生的叔胺/硫脲催化剂；这类催化剂以高度对映选择性的方式促进了设计的多米诺骨牌迈克尔-烷基化反应（参见方案）。