(1E,3Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1E,3Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone
• 英文别名: 3-methyl-3-[(1E,3Z)-4-methylsulfanyl-2-nitrobuta-1,3-dienyl]oxolan-2-one
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: QGOLPQPPYJTMKM-NEEAAVDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1E,3Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone 以 氘代氯仿 为溶剂， 以20%的产率得到(Z,Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone
  参考文献：
  名称：

  Nitroalkylation and nitroalkenylation reactions of γ-lactone enolates. A facile ring switch from polysubstituted γ-lactones to polysubstituted γ-lactams

  摘要：

  Michael addition of lithium enolates of gamma-butyrolactone 1 and alpha-methyl-gamma-butyrolactone 1' to (E)-1-nitropropene 2, (E)-beta-nitrostyrene 3 and (E)-2-vitro-1-phenylpropene 4 is described. Reactions of the lithium enolate of 1' with 2 and 4 occurred with high diasteroselectivity (80 and 92% d.e., respectively). Reactions of the zinc enolate of 1' with two beta-nitroenamines and two methylthiosubstituted 1-amino-2-vitro-1,3-dienes were also examined. Catalytic reduction of the nitroalkylated and nitroalkenylated products allowed the achievement of functionalized gamma-lactams and/or cyclic hydroxamic acids. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.084
• 作为产物：
  描述：

  (1Z,3E)-1-methylthio-4-pyrrolidinyl-3-nitro-1,3-butadiene 、 α-甲基-γ-丁内酯 在 lithium diisopropyl amide 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以52%的产率得到(1E,3Z)-4,5-dihydro-3-methyl-3-[4-(methylthio)-2-nitrobuta-1,3-dien-1-yl]-2(3H)-furanone
  参考文献：
  名称：

  Nitroalkylation and nitroalkenylation reactions of γ-lactone enolates. A facile ring switch from polysubstituted γ-lactones to polysubstituted γ-lactams

  摘要：

  Michael addition of lithium enolates of gamma-butyrolactone 1 and alpha-methyl-gamma-butyrolactone 1' to (E)-1-nitropropene 2, (E)-beta-nitrostyrene 3 and (E)-2-vitro-1-phenylpropene 4 is described. Reactions of the lithium enolate of 1' with 2 and 4 occurred with high diasteroselectivity (80 and 92% d.e., respectively). Reactions of the zinc enolate of 1' with two beta-nitroenamines and two methylthiosubstituted 1-amino-2-vitro-1,3-dienes were also examined. Catalytic reduction of the nitroalkylated and nitroalkenylated products allowed the achievement of functionalized gamma-lactams and/or cyclic hydroxamic acids. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.084

文献信息

• Nitroalkylation and nitroalkenylation reactions of γ-lactone enolates. A facile ring switch from polysubstituted γ-lactones to polysubstituted γ-lactams
  作者：C. Forzato、P. Nitti、G. Pitacco、E. Valentin、S. Morganti、E. Rizzato、D. Spinelli、C. Dell'Erba、G. Petrillo、C. Tavani

  DOI：10.1016/j.tet.2004.07.084

  日期：2004.11

  Michael addition of lithium enolates of gamma-butyrolactone 1 and alpha-methyl-gamma-butyrolactone 1' to (E)-1-nitropropene 2, (E)-beta-nitrostyrene 3 and (E)-2-vitro-1-phenylpropene 4 is described. Reactions of the lithium enolate of 1' with 2 and 4 occurred with high diasteroselectivity (80 and 92% d.e., respectively). Reactions of the zinc enolate of 1' with two beta-nitroenamines and two methylthiosubstituted 1-amino-2-vitro-1,3-dienes were also examined. Catalytic reduction of the nitroalkylated and nitroalkenylated products allowed the achievement of functionalized gamma-lactams and/or cyclic hydroxamic acids. (C) 2004 Elsevier Ltd. All rights reserved.