(Z)-4-Nitro-5-phenyl-pent-4-enoic acid ethyl ester | 52175-26-5

• 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: (Z)-4-Nitro-5-phenyl-pent-4-enoic acid ethyl ester
• 英文别名: Ethyl 4-nitro-5-phenylpent-4-enoate
• CAS: 52175-26-5
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: STGXHVBKOHDVJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (Z)-4-Nitro-5-phenyl-pent-4-enoic acid ethyl ester 在 lithium aluminium tetrahydride 、 四溴化碳 、 sodium ethanolate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Regioselective Synthesis of Sulfonylpyrazoles via Base Mediated Reaction of Diazosulfones with Nitroalkenes and a Facile Entry into Withasomnine

  摘要：

  A base mediated reaction of alpha-diazo-beta-ketosulfone with nitroalkenes affords sulfonylpyrazoles as single regioisomers in excellent yield in a one-pot room temperature reaction. Aryl, heteroaryl, styrenyl, alkyl, hydroxymethyl, and hydrazinyl groups could be introduced on the pyrazole ring by the appropriate choice of nitroalkenes. Synthesis of sulfonylpyrazole fused to other heterocycles and application of the methodology to an expedient synthesis of a pyrazole alkaloid, Withasomnine, are also reported.

  DOI：

  10.1021/ol201534f
• 作为产物：
  描述：

  β-硝基苯乙烯 、 丙烯酸乙酯 生成 (Z)-4-Nitro-5-phenyl-pent-4-enoic acid ethyl ester
  参考文献：
  名称：

  Regioselective Synthesis of Sulfonylpyrazoles via Base Mediated Reaction of Diazosulfones with Nitroalkenes and a Facile Entry into Withasomnine

  摘要：

  A base mediated reaction of alpha-diazo-beta-ketosulfone with nitroalkenes affords sulfonylpyrazoles as single regioisomers in excellent yield in a one-pot room temperature reaction. Aryl, heteroaryl, styrenyl, alkyl, hydroxymethyl, and hydrazinyl groups could be introduced on the pyrazole ring by the appropriate choice of nitroalkenes. Synthesis of sulfonylpyrazole fused to other heterocycles and application of the methodology to an expedient synthesis of a pyrazole alkaloid, Withasomnine, are also reported.

  DOI：

  10.1021/ol201534f

文献信息

• Phosphonylpyrazoles from Bestmann−Ohira Reagent and Nitroalkenes: Synthesis and Dynamic NMR Studies
  作者：Rajendran Muruganantham、Irishi Namboothiri

  DOI：10.1021/jo902595e

  日期：2010.4.2

  also included Morita−Baylis−Hillman adducts of conjugated nitroalkenes with various electrophiles. Detailed dynamic NMR studies were performed on the prototropic tautomerism exhibited by the phosphonylpyrazoles using CDCl3 and DMSO-d6 as solvents and 1H and 31P as the probe nuclei. These studies unraveled the existence of two tautomers in solution with a small energy difference but considerable barrier

  1-重氮-2-氧代丙基膦酸二乙酯（Bestmann-Ohira试剂）作为硝基烯与环加成伙伴的应用已得到广泛研究。Bestmann-Ohira试剂与各种硝基烯烃（例如，碳环或杂环的一部分的β-取代的，α，β-二取代的和硝基乙烯）进行的碱介导反应通过室温下的一锅区域选择性反应提供了官能化的磷酸ny唑。高产。这些反应中使用的取代硝基烯烃还包括共轭硝基烯烃与各种亲电试剂的森田-贝利斯-希尔曼加合物。使用CDCl 3和DMSO- d 6作为溶剂，对膦酰基吡唑显示的质子互变异构进行了详细的动态NMR研究。1 H和31 P作为探针核。这些研究揭示了溶液中两种互变异构体的存在，它们的能量差很小，但对互变具有很大的障碍。
• Gaur, S. P.; Jain, Padam C.; Anand, Nitya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 1, p. 46 - 51
  作者：Gaur, S. P.、Jain, Padam C.、Anand, Nitya

  DOI：——

  日期：——
• Regioselective Synthesis of Sulfonylpyrazoles via Base Mediated Reaction of Diazosulfones with Nitroalkenes and a Facile Entry into Withasomnine
  作者：Rahul Kumar、Irishi N. N. Namboothiri

  DOI：10.1021/ol201534f

  日期：2011.8.5

  A base mediated reaction of alpha-diazo-beta-ketosulfone with nitroalkenes affords sulfonylpyrazoles as single regioisomers in excellent yield in a one-pot room temperature reaction. Aryl, heteroaryl, styrenyl, alkyl, hydroxymethyl, and hydrazinyl groups could be introduced on the pyrazole ring by the appropriate choice of nitroalkenes. Synthesis of sulfonylpyrazole fused to other heterocycles and application of the methodology to an expedient synthesis of a pyrazole alkaloid, Withasomnine, are also reported.