rel-(4S,4'R)-bis(4-anisyl-5,5-dimethyl-4,5-dihydro-1H-pyrazol-3-yl)ketone | 220656-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: rel-(4S,4'R)-bis(4-anisyl-5,5-dimethyl-4,5-dihydro-1H-pyrazol-3-yl)ketone
• 英文别名: [(4R)-4-(4-methoxyphenyl)-5,5-dimethyl-1,4-dihydropyrazol-3-yl]-[(4S)-4-(4-methoxyphenyl)-5,5-dimethyl-1,4-dihydropyrazol-3-yl]methanone
• CAS: 220656-29-1
• 化学式: C₂₅H₃₀N₄O₃
• 分子量: 434.538
• InChiKey: VPEXFVXQPCRLNP-BGYRXZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rel-(4S,4'R)-bis(4-anisyl-5,5-dimethyl-4,5-dihydro-1H-pyrazol-3-yl)ketone 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (4-anisyl-3,3-dimethyl-5-yl)(4-anisyl-5,5-dimethyl-4,5-dihydro-1H-pyrazol-3-yl)ketone
  参考文献：
  名称：

  Steroe- and chemoselectivity in 1,3-dipolar cycloaddition reaction of 2-diazopropane with diarylidenacetones

  摘要：

  1,3-Dipolar cycloaddition reaction of 2-diazopropane I with diarylideneacetones 2 carried out at 0 degrees C led to a minor Delta(2)-pyrazoline monocycloadduct 4 and two diastereoisomeric bicycloadducts 5 and 6. The same addition realised at -60 degrees C has enabled us to observe, beside bis-Delta(2)-pyrazolines 5 and 6, the formation of unexpected Delta(3)-(1,3,4)oxadiazoline derivatives 9 and 10. These two diastereoisomers result from the addition of 2-diazopropane on the carbonyl of unstable Delta(1)-pyrazoline intermediates 3' and 3 " with an unusual regiochemical way. Oxidation of 5 and 6 gave 3H-pyrazoles 7 and 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01056-4
• 作为产物：
  描述：

  (1E,4e)-1,5-双(4-甲氧基苯基)-1,4-戊二烯-3-酮 、 2-重氮丙烷 以 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 rel-(4R)-(4-anisyl-5,5-dimethyl-4,5-dihydro-1H-pyrazol-3-yl)(2-phenylethenyl)ketone 、 rel-(4S,4'R)-bis(4-anisyl-5,5-dimethyl-4,5-dihydro-1H-pyrazol-3-yl)ketone 、 rel-(4S,4'S)-bis(4-anisyl-5,5-dimethyl-4,5-dihydro-1H-pyrazol-3-yl)ketone
  参考文献：
  名称：

  Steroe- and chemoselectivity in 1,3-dipolar cycloaddition reaction of 2-diazopropane with diarylidenacetones

  摘要：

  1,3-Dipolar cycloaddition reaction of 2-diazopropane I with diarylideneacetones 2 carried out at 0 degrees C led to a minor Delta(2)-pyrazoline monocycloadduct 4 and two diastereoisomeric bicycloadducts 5 and 6. The same addition realised at -60 degrees C has enabled us to observe, beside bis-Delta(2)-pyrazolines 5 and 6, the formation of unexpected Delta(3)-(1,3,4)oxadiazoline derivatives 9 and 10. These two diastereoisomers result from the addition of 2-diazopropane on the carbonyl of unstable Delta(1)-pyrazoline intermediates 3' and 3 " with an unusual regiochemical way. Oxidation of 5 and 6 gave 3H-pyrazoles 7 and 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01056-4

文献信息

• Steroe- and chemoselectivity in 1,3-dipolar cycloaddition reaction of 2-diazopropane with diarylidenacetones
  作者：N. Boukamcha、R. Gharbi、M.-T. Martin、A. Chiaroni、Z. Mighri、A. Khemiss

  DOI：10.1016/s0040-4020(98)01056-4

  日期：1999.1

  1,3-Dipolar cycloaddition reaction of 2-diazopropane I with diarylideneacetones 2 carried out at 0 degrees C led to a minor Delta(2)-pyrazoline monocycloadduct 4 and two diastereoisomeric bicycloadducts 5 and 6. The same addition realised at -60 degrees C has enabled us to observe, beside bis-Delta(2)-pyrazolines 5 and 6, the formation of unexpected Delta(3)-(1,3,4)oxadiazoline derivatives 9 and 10. These two diastereoisomers result from the addition of 2-diazopropane on the carbonyl of unstable Delta(1)-pyrazoline intermediates 3' and 3 " with an unusual regiochemical way. Oxidation of 5 and 6 gave 3H-pyrazoles 7 and 8. (C) 1998 Elsevier Science Ltd. All rights reserved.