ethyl (3R,4S)-3-benzoyl-2,4-diphenyl-3,4-dihydropyrazole-5-carboxylate | 90878-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (3R,4S)-3-benzoyl-2,4-diphenyl-3,4-dihydropyrazole-5-carboxylate
• CAS: 90878-44-7
• 化学式: C₂₅H₂₂N₂O₃
• 分子量: 398.461
• InChiKey: KCRXASQYTQNLMF-FYYLOGMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (3R,4S)-3-benzoyl-2,4-diphenyl-3,4-dihydropyrazole-5-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以62%的产率得到ethyl 1,4-diphenyl-5-benzoylpyrazole-3-carboxylate
  参考文献：
  名称：

  Nuclear magnetic resonance spectroscopy and the structures of the regioisomeric products of the cycloaddition of C-ethoxycarbonyl-N-arylnitrilimines to α,β-unsaturated ketones

  摘要：

  H-1 NMR chemical shifts were used to assign the structures of the regioisomeric products obtained from the reactions of C-ethoxycarbonyl-N-arylnitrilimines 2A-E to alpha,beta-unsaturated ketones 3a-j. The assignments were based on the large observed difference between chemical shifts of the H-4 and H-5 of the 2-pyrazoline ring residue. Values of 1.29 +/- 0.06 and 0.34 +/- 0.03 ppm were found for DELTA-delta-4,5 for the 5-aroyl- and 4-aroyl-2-pyrazoline regioisomers 4 and 5, respectively. The regioselectivity in the studied cycloaddition reactions is interpreted in terms of FMO method.

  DOI：

  10.1016/0584-8539(92)80127-i
• 作为产物：
  描述：

  ethyl (phenylhydrazono)chloroacetate 、 反式-查耳酮 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 ethyl (3R,4S)-3-benzoyl-2,4-diphenyl-3,4-dihydropyrazole-5-carboxylate
  参考文献：
  名称：

  Hassaneen, Hamdi M.; Hilal, Rifaat H.; Elwan, Nehal M., Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1013 - 1016

  摘要：

  DOI：

文献信息

• The Reaction of<i>N</i>-Aryl-<i>C</i>-ethoxycarbonylnitrilimine with Olefins
  作者：Tomio Shimizu、Yoshiyuki Hayashi、Toshiyuki Nishio、Kazuhiro Teramura

  DOI：10.1246/bcsj.57.787

  日期：1984.3

  C-Ethoxycarbonylnitrilimines treated with monosubstituted olefins predominantly gave 5-substituted 3-ethoxycarbonyl-2-pyrazolines. From the analysis of the relative rate and regioselectivity of a variety of monosubstituted olefins for the cycloaddition, the nitrilimine is shown to have reactivity and regioselectivity similar to the throughly studied diphenylnitrilimine. The cycloaddition regioselectivity is discussed in terms of frontier orbital energies and coefficients.

  用单取代的烯烃处理C-乙氧基羰基氮亚胺主要产生5-取代的3-乙氧基羰基-2-吡唑啉。通过对各种单取代烯烃环加成反应的相对速率和区域选择性的分析，表明氮亚胺具有与经过深入研究的二苯基氮亚胺类似的反应活性和区域选择性。根据前沿轨道能量和系数讨论了环加成区域选择性。
• SHIMIZU, TOMIO;HAYASHI, YOSHIYUKI;NISHIO, TOSHIYUKI;TERAMURA, KAZUHIRO, BULL. CHEM. SOC. JAP., 1984, 57, N 3, 787-790
  作者：SHIMIZU, TOMIO、HAYASHI, YOSHIYUKI、NISHIO, TOSHIYUKI、TERAMURA, KAZUHIRO

  DOI：——

  日期：——
• Hassaneen, Hamdi M.; Hilal, Rifaat H.; Elwan, Nehal M., Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1013 - 1016
  作者：Hassaneen, Hamdi M.、Hilal, Rifaat H.、Elwan, Nehal M.、Harhash, Abdelhamid、Shawali, Ahmad S.

  DOI：——

  日期：——
• Nuclear magnetic resonance spectroscopy and the structures of the regioisomeric products of the cycloaddition of C-ethoxycarbonyl-N-arylnitrilimines to α,β-unsaturated ketones
  作者：Ahmad S. Shawali、Saleh T. Ezmirly、Ahmad M. Bukhari

  DOI：10.1016/0584-8539(92)80127-i

  日期：1992.8

  H-1 NMR chemical shifts were used to assign the structures of the regioisomeric products obtained from the reactions of C-ethoxycarbonyl-N-arylnitrilimines 2A-E to alpha,beta-unsaturated ketones 3a-j. The assignments were based on the large observed difference between chemical shifts of the H-4 and H-5 of the 2-pyrazoline ring residue. Values of 1.29 +/- 0.06 and 0.34 +/- 0.03 ppm were found for DELTA-delta-4,5 for the 5-aroyl- and 4-aroyl-2-pyrazoline regioisomers 4 and 5, respectively. The regioselectivity in the studied cycloaddition reactions is interpreted in terms of FMO method.