(R)-methyl 6-amino-5-cyano-4-(4-nitrophenyl)-4H-pyran-2-carboxylate | 1171110-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-methyl 6-amino-5-cyano-4-(4-nitrophenyl)-4H-pyran-2-carboxylate
• 英文别名: methyl (4R)-6-amino-5-cyano-4-(4-nitrophenyl)-4H-pyran-2-carboxylate
• CAS: 1171110-69-2
• 化学式: C₁₄H₁₁N₃O₅
• 分子量: 301.258
• InChiKey: SBTORKBARRVKAS-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Methyl 4-(4-nitrophenyl)-2-oxobut-3-enoate 、 丙二腈 在 1-[3,5-双(三氟甲基)苯基]-3-[(1R,2R)-(-)-2-(二甲氨基)环己基]硫脲 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以50%的产率得到(R)-methyl 6-amino-5-cyano-4-(4-nitrophenyl)-4H-pyran-2-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of multifunctionalized 4H-pyran derivatives using bifunctional thiourea-tertiary amine catalysts

  摘要：

  A series of novel chiral multifunctionalized 4H-pyran derivatives were easily accessed via the one-pot asymmetric Michael addition-cyclization reaction between malononitrile and beta,gamma-unsaturated alpha-keto esters catalyzed by chiral bifunctional thiourea-tertiary amine catalysts. With the optimized reaction conditions, the desired products were obtained with 50-68% yields and 72-88% ees. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.054

文献信息

• Enantioselective synthesis of multifunctionalized 4H-pyran derivatives using bifunctional thiourea-tertiary amine catalysts
  作者：Sheng-Li Zhao、Chang-Wu Zheng、Gang Zhao

  DOI：10.1016/j.tetasy.2009.02.054

  日期：2009.5

  A series of novel chiral multifunctionalized 4H-pyran derivatives were easily accessed via the one-pot asymmetric Michael addition-cyclization reaction between malononitrile and beta,gamma-unsaturated alpha-keto esters catalyzed by chiral bifunctional thiourea-tertiary amine catalysts. With the optimized reaction conditions, the desired products were obtained with 50-68% yields and 72-88% ees. (c) 2009 Elsevier Ltd. All rights reserved.