(1R,2R,4R)-2-benzoylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester | 195515-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,4R)-2-benzoylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester
• 英文别名: ethyl (1R,2R,4R)-2-benzoylbicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 195515-50-5
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: DVCAYBKPUKBOHP-HACGYAERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R)-2-benzoylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester 在 溴 作用下， 以 四氯化碳 为溶剂， 以92%的产率得到(1R,3R,6R,7S)-3-benzoyl-9-bromo-5-oxacyclo[4.2.1.0^3,7]nonane-4-one
  参考文献：
  名称：

  Reactivity of 2-methylene-1,3-dicarbonyl compounds: catalytic enantioselective Diels–Alder reaction

  摘要：

  The catalytic enantioselective Diets-Alder reaction of 1,1-dicarbonylethenes 3 with cyclopentadiene in the presence of Ti-TADDOLs, Mg-Ph-box and Mg-Ph-mox complexes was investigated. Although both exo- and enantioselectivity with Ti-TADDOL catalysts were poor, they were much improved using Mg-Ph-box or Mg-Ph-mox complexes as chiral catalysts. Thus, 3 was an efficient two-point binding dienophile and the non-C-2-syrrimetric Ph-mox 8 could be used as a chiral ligand. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00559-6
• 作为产物：
  描述：

  ethyl 2-benzoylacrylate 、 环戊二烯 、 氯化锌 生成 (1R,2R,4R)-2-benzoylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  YAMAUCHI, MASASHIGE;WATANABE, TOSHIO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 1, 27-28

  摘要：

  DOI：

文献信息

• Enantioselective catalytic Diels–Alder reaction of ethyl 2-benzoylacrylate with chiral bis(oxazoline)– or mono(oxazoline)–magnesium complex
  作者：Yuko Honda、Tadamasa Date、Hajime Hiramatsu、Masashige Yamauchi

  DOI：10.1039/a702920i

  日期：——

  The magnesium catalysed Diels–Alder reaction of 2-benzoylacrylate gave the endo-adduct enantioselectively with bis(oxazoline) 5 as a C 2 -symmetric ligand or mono(oxazoline) 4 as a non-C 2 -symmetric ligand.

  在镁催化下，2-苯甲酰基丙烯酸酯与作为 C 2 - 不对称配体的双（噁唑啉）5 或作为非 C 2 - 不对称配体的单（噁唑啉）4 发生 DielsâAlder 反应，产生了对映体加成物。
• YAMAUCHI, MASASHIGE;WATANABE, TOSHIO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 1, 27-28
  作者：YAMAUCHI, MASASHIGE、WATANABE, TOSHIO

  DOI：——

  日期：——
• Reactivity of 2-methylene-1,3-dicarbonyl compounds: catalytic enantioselective Diels–Alder reaction
  作者：Masashige Yamauchi、Takashi Aoki、Ming-Zhu Li、Yuko Honda

  DOI：10.1016/s0957-4166(01)00559-6

  日期：2001.12

  The catalytic enantioselective Diets-Alder reaction of 1,1-dicarbonylethenes 3 with cyclopentadiene in the presence of Ti-TADDOLs, Mg-Ph-box and Mg-Ph-mox complexes was investigated. Although both exo- and enantioselectivity with Ti-TADDOL catalysts were poor, they were much improved using Mg-Ph-box or Mg-Ph-mox complexes as chiral catalysts. Thus, 3 was an efficient two-point binding dienophile and the non-C-2-syrrimetric Ph-mox 8 could be used as a chiral ligand. (C) 2002 Elsevier Science Ltd. All rights reserved.