ethyl 4-hydroxy-6-(naphthalen-2-yl)-7-nitro-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate | 1266754-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 4-hydroxy-6-(naphthalen-2-yl)-7-nitro-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate
• 英文别名: ethyl (3aS,6R,7S,7aR)-4-hydroxy-6-naphthalen-2-yl-7-nitro-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate
• CAS: 1266754-52-2
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: LCEFKWSSDXYBGJ-RMJJICAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 四甲基胍 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以37.7 mg的产率得到ethyl 4-hydroxy-6-(naphthalen-2-yl)-7-nitro-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

文献信息

• Organocatalytic Sequential Michael Reactions: Stereoselective Synthesis of Multifunctionalized Tetrahydroindan Derivatives
  作者：Peng He、Xiaohua Liu、Jian Shi、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol1029832

  日期：2011.3.4

  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.