4-trifluoromethylbenzoic acid endo-3-(2-oxo-pyrrolidine-3-carbonyl)-bicyclo[2.2.1]hept-5-en-2-yl ester | 740815-65-0

• 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: 4-trifluoromethylbenzoic acid endo-3-(2-oxo-pyrrolidine-3-carbonyl)-bicyclo[2.2.1]hept-5-en-2-yl ester
• 英文别名: [(1R,2R,3R,4S)-3-(2-oxopyrrolidine-1-carbonyl)-2-bicyclo[2.2.1]hept-5-enyl] 4-(trifluoromethyl)benzoate
• CAS: 740815-65-0
• 化学式: C₂₀H₁₈F₃NO₄
• 分子量: 393.362
• InChiKey: BDVKAUXXHRBBSV-DLTLXFJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-trifluoromethylbenzoic acid endo-3-(2-oxo-pyrrolidine-3-carbonyl)-bicyclo[2.2.1]hept-5-en-2-yl ester 在 1,1-bis(8,8a,3a-tri(H)-indeno[1,2-d]oxazol-2yl)cPr*Cu(SbF₆)2 、 samarium(III) trifluoromethanesulfonate 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 24.33h， 生成 甲基(1S,4R)-双环[2.2.1]庚-2,5-二烯-2-羧酸酯
  参考文献：
  名称：

  Enantioselective Diels–Alder reactions of 3-(acyloxy)acrylates

  摘要：

  Diels-Alder reactions with 3-(acyloxy)acrylates using chiral Lewis acid catalysts have been successfully carried out. These reactions proceed with high enantioselectivity when a chiral Lewis acid derived from Cu(OTf)(2) and a bisoxazoline is used. The facility of the reaction is dependent on the nature of the acyloxy group in the dienophile. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.090
• 作为产物：
  描述：

  1-(3-chloroacryloyl)-2-pyrrolidinone 在 1,1-bis(8,8a,3a-tri(H)-indeno[1,2-d]oxazol-2yl)cPr*Cu(SbF₆)2 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 25.5h， 生成 4-trifluoromethylbenzoic acid endo-3-(2-oxo-pyrrolidine-3-carbonyl)-bicyclo[2.2.1]hept-5-en-2-yl ester
  参考文献：
  名称：

  Enantioselective Diels–Alder reactions of 3-(acyloxy)acrylates

  摘要：

  Diels-Alder reactions with 3-(acyloxy)acrylates using chiral Lewis acid catalysts have been successfully carried out. These reactions proceed with high enantioselectivity when a chiral Lewis acid derived from Cu(OTf)(2) and a bisoxazoline is used. The facility of the reaction is dependent on the nature of the acyloxy group in the dienophile. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.090

文献信息

• Enantioselective Diels–Alder reactions of 3-(acyloxy)acrylates
  作者：Mukund P. Sibi、Hirofumi Matsunaga

  DOI：10.1016/j.tetlet.2004.05.090

  日期：2004.7

  Diels-Alder reactions with 3-(acyloxy)acrylates using chiral Lewis acid catalysts have been successfully carried out. These reactions proceed with high enantioselectivity when a chiral Lewis acid derived from Cu(OTf)(2) and a bisoxazoline is used. The facility of the reaction is dependent on the nature of the acyloxy group in the dienophile. (C) 2004 Elsevier Ltd. All rights reserved.