(E)-methyl 5-nitropent-2-enoate | 67810-58-6

• 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: (E)-methyl 5-nitropent-2-enoate
• 英文别名: 5-Nitro-pent-2-ensaeure-methylester；Methyl (E)-5-nitro-2-pentenoat；methyl (E)-5-nitropent-2-enoate
• CAS: 67810-58-6
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: HANFSKQIDADPNC-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-亚苄基-4-甲基苯磺酰胺 、 (E)-methyl 5-nitropent-2-enoate 在 C₃₅H₄₇N₃O₂ 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到methyl 2-((2S, 4R, 5S)-4-nitro-5-phenyl-1-tosylpyrrolidin-2-yl)acetate
  参考文献：
  名称：

  A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade

  摘要：

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.

  DOI：

  10.1021/ol4006129
• 作为产物：
  描述：

  (2E)-5-羟基-2-戊烯酸甲酯 在 silver(I) nitrite 、 三乙胺 、 lithium bromide 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 生成 (E)-methyl 5-nitropent-2-enoate
  参考文献：
  名称：

  Synthesis in the tropane class of alkaloids. Pseudotropine and dl-cocaine

  摘要：

  DOI：

  10.1021/ja00503a033

文献信息

• Synthesis in the tropane class of alkaloids. Pseudotropine and dl-cocaine
  作者：Joseph J. Tufariello、George B. Mullen、John J. Tegeler、Eugene J. Trybulski、Shing Chun Wong、S. Asrof Ali

  DOI：10.1021/ja00503a033

  日期：1979.4
• A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade
  作者：Tao Cheng、Sixuan Meng、Yong Huang

  DOI：10.1021/ol4006129

  日期：2013.4.19

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.