2-methyl-3,4-bis(p-bromophenyl)-5-phenylcyclopentadienone | 170935-97-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-methyl-3,4-bis(p-bromophenyl)-5-phenylcyclopentadienone
• CAS: 170935-97-4
• 化学式: C₂₄H₁₆Br₂O
• 分子量: 480.198
• InChiKey: FYBIDZGOLMDMLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-D-galacto-hept-1-enitol 、 2-methyl-3,4-bis(p-bromophenyl)-5-phenylcyclopentadienone 以 甲苯 为溶剂， 反应 72.0h， 以45%的产率得到(5S,6R)-1-methyl-2,3-bis(4-bromophenyl)-4-phenyl-5-exo-(D-galacto-penta-O-acetylpentitol-1-yl)-6-endo-nitrobicyclo<2.2.1>hept-2-en-7-one
  参考文献：
  名称：

  Diastereoselective synthesis of C-glycosylnorbornenones

  摘要：

  Thermal reaction of (E)-3,4,5,6,7-penra-O-aceryl-1,2-dideoxy (la)and-D-manno-hept-1-enitol (1b) with 2-methyl-3,4-diaryl-5-phenylcyclopentadienones (2a-c) afforded diastereoselectively 1-methyl-2,3-diruyl-4-phenyl-(5S,6R)-5-exo-(D-galacto- (3a-c) and -(SR,6S)-5-exo-(D-manno-penta-O-acetylpentitol-1-yl)-6-endo- nitrobicyclo[2.2.1]hept-2-en-7-ones (6a-c) and variable amounts of the 1-phenyl-4-methyl regioisomers 4a-e and 7a-c, depending upon the p-subsrituent in the aryl moiety. 1-C-Arylalditols 5, 8-9 are also obtained in refluxing xylene.

  DOI：

  10.1016/0040-4020(95)00428-b
• 作为产物：
  描述：

  3-苯基-2-丁酮 、 4,4'-二溴联苯酰 以78%的产率得到2-methyl-3,4-bis(p-bromophenyl)-5-phenylcyclopentadienone
  参考文献：
  名称：

  Diastereoselective synthesis of C-glycosylnorbornenones

  摘要：

  Thermal reaction of (E)-3,4,5,6,7-penra-O-aceryl-1,2-dideoxy (la)and-D-manno-hept-1-enitol (1b) with 2-methyl-3,4-diaryl-5-phenylcyclopentadienones (2a-c) afforded diastereoselectively 1-methyl-2,3-diruyl-4-phenyl-(5S,6R)-5-exo-(D-galacto- (3a-c) and -(SR,6S)-5-exo-(D-manno-penta-O-acetylpentitol-1-yl)-6-endo- nitrobicyclo[2.2.1]hept-2-en-7-ones (6a-c) and variable amounts of the 1-phenyl-4-methyl regioisomers 4a-e and 7a-c, depending upon the p-subsrituent in the aryl moiety. 1-C-Arylalditols 5, 8-9 are also obtained in refluxing xylene.

  DOI：

  10.1016/0040-4020(95)00428-b

文献信息

• Diastereoselective synthesis of C-glycosylnorbornenones
  作者：José L. Del Valle、Tomás Torroba、Stefane Marcaccini、Paola Paoli、David J. Williams

  DOI：10.1016/0040-4020(95)00428-b

  日期：1995.7

  Thermal reaction of (E)-3,4,5,6,7-penra-O-aceryl-1,2-dideoxy (la)and-D-manno-hept-1-enitol (1b) with 2-methyl-3,4-diaryl-5-phenylcyclopentadienones (2a-c) afforded diastereoselectively 1-methyl-2,3-diruyl-4-phenyl-(5S,6R)-5-exo-(D-galacto- (3a-c) and -(SR,6S)-5-exo-(D-manno-penta-O-acetylpentitol-1-yl)-6-endo- nitrobicyclo[2.2.1]hept-2-en-7-ones (6a-c) and variable amounts of the 1-phenyl-4-methyl regioisomers 4a-e and 7a-c, depending upon the p-subsrituent in the aryl moiety. 1-C-Arylalditols 5, 8-9 are also obtained in refluxing xylene.