ethyl 2-(cyclopent-1-enecarbonyl)-4-nitro-3-phenylbutanoate | 1266754-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(cyclopent-1-enecarbonyl)-4-nitro-3-phenylbutanoate
• CAS: 1266754-78-2
• 化学式: C₁₈H₂₁NO₅
• 分子量: 331.368
• InChiKey: LVOQYLSICZRDQG-AAFJCEBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(cyclopent-1-enecarbonyl)-4-nitro-3-phenylbutanoate 在 四甲基胍 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以32.8 mg的产率得到ethyl 4-hydroxy-7-nitro-6-phenyl-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate
  参考文献：
  名称：

  Organocatalytic Sequential Michael Reactions: Stereoselective Synthesis of Multifunctionalized Tetrahydroindan Derivatives

  摘要：

  Multifunctionalized tetrahydroindan derivatives with four stereocenters were constructed via two sequential Michael reactions between cyclic gamma,delta-unsaturated-beta-ketoester and nitroalkenes initiated with 0.5-2 mol % of cinchona alkaloid based bifunctional organocatalysts and then with 1 equiv of tetramethylguanidine for cyclization. The desired products could be obtained in high yields (up to 99% yield) with excellent enantioselectivities (95-99% ee) as well as diastereoselectivities (up to >99:1 dr) even on a gram scale.

  DOI：

  10.1021/ol1029832
• 作为产物：
  描述：

  β-硝基苯乙烯 、 3-Oxo-3--propionsaeureaethylester 在 (8Α,9R)-9-(9-苯基甲氧基)奎宁-6'-醇 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 ethyl 2-(cyclopent-1-enecarbonyl)-4-nitro-3-phenylbutanoate
  参考文献：
  名称：

  Organocatalytic Sequential Michael Reactions: Stereoselective Synthesis of Multifunctionalized Tetrahydroindan Derivatives

  摘要：

  Multifunctionalized tetrahydroindan derivatives with four stereocenters were constructed via two sequential Michael reactions between cyclic gamma,delta-unsaturated-beta-ketoester and nitroalkenes initiated with 0.5-2 mol % of cinchona alkaloid based bifunctional organocatalysts and then with 1 equiv of tetramethylguanidine for cyclization. The desired products could be obtained in high yields (up to 99% yield) with excellent enantioselectivities (95-99% ee) as well as diastereoselectivities (up to >99:1 dr) even on a gram scale.

  DOI：

  10.1021/ol1029832