1,4-dimethyl-2,3-diphenylfulvene | 51985-23-0

• 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: 1,4-dimethyl-2,3-diphenylfulvene
• 英文别名: (2,4-Dimethyl-3-methylidene-5-phenylcyclopenta-1,4-dien-1-yl)benzene
• CAS: 51985-23-0
• 化学式: C₂₀H₁₈
• 分子量: 258.363
• InChiKey: QKUVGYVQJVSFKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-dimethyl-2,3-diphenylfulvene 、 二苯基膦 、 iron(II) chloride 在 lithium 作用下， 以 四氢呋喃 为溶剂， 以45.8%的产率得到1,1'-bis-diphenylphosphinomethyl-2,2',5,5'-tetramethyl-3,3',4,4'-tetraphenylferrocene
  参考文献：
  名称：

  1,4-Dimethyl-2,3-diphenylfulvene: A convenient precursor to heteroatom-substituted-1-methyl-2,5-dimethyl-3,4-diphenylcyclopentadienyl transition metal complexes

  摘要：

  Reaction of 2,5-dimethyl-3,4-diphenylcyclopent-2-enone (1) with Ph(3)P=CH2 in THF gave 2,5-dimethyl-3,4-diphenylcyclopent-2-ene-1-ylidene (2) in 75% yield. Treatment of 2 with one equivalent of Br-2, followed by two equivalents of triethylamine gave 1,4-dimethyl-2,3-diphenylfulvene (3) in 60% overall yield. Treatment of 3 with LiCH3 and LiC6H5 followed by FeCl2 gave [eta(5)-1-CH3CH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2 and [eta(5)-1-C6H5CH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2, respectively, in good yield. Treatment of 3 with LiNHC(CH3)(3) and LiP(C6H5)(2) followed by FeCl2 gave [eta(5)-1-(CH3)(3)CNHCH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2 and [eta(5)-1-(C6H5)(2)PCH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2, respectively, in good yield. Treatment of 3 with (R)-LiNHCH(CH3)C6H5 followed by FeCl2 gave the corresponding enantiomerically pure ferrocene complex (R,R)-[eta(5)-1-C6H5CH(CH3)NHCH2-2.5-(CH3)(2)- 3,4-(C6H5)(2)C-5]Fe-2 in 44% yield.

  DOI：

  10.1016/0022-328x(95)06083-9
• 作为产物：
  描述：

  2,5-dimethyl-3,4-diphenylcyclopent-2-en-1-one 在 甲基锂 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 53.5h， 生成 1,4-dimethyl-2,3-diphenylfulvene
  参考文献：
  名称：

  1,4-Dimethyl-2,3-diphenylfulvene: A convenient precursor to heteroatom-substituted-1-methyl-2,5-dimethyl-3,4-diphenylcyclopentadienyl transition metal complexes

  摘要：

  Reaction of 2,5-dimethyl-3,4-diphenylcyclopent-2-enone (1) with Ph(3)P=CH2 in THF gave 2,5-dimethyl-3,4-diphenylcyclopent-2-ene-1-ylidene (2) in 75% yield. Treatment of 2 with one equivalent of Br-2, followed by two equivalents of triethylamine gave 1,4-dimethyl-2,3-diphenylfulvene (3) in 60% overall yield. Treatment of 3 with LiCH3 and LiC6H5 followed by FeCl2 gave [eta(5)-1-CH3CH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2 and [eta(5)-1-C6H5CH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2, respectively, in good yield. Treatment of 3 with LiNHC(CH3)(3) and LiP(C6H5)(2) followed by FeCl2 gave [eta(5)-1-(CH3)(3)CNHCH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2 and [eta(5)-1-(C6H5)(2)PCH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2, respectively, in good yield. Treatment of 3 with (R)-LiNHCH(CH3)C6H5 followed by FeCl2 gave the corresponding enantiomerically pure ferrocene complex (R,R)-[eta(5)-1-C6H5CH(CH3)NHCH2-2.5-(CH3)(2)- 3,4-(C6H5)(2)C-5]Fe-2 in 44% yield.

  DOI：

  10.1016/0022-328x(95)06083-9

文献信息

• Hamer,N.K.; Wills,A.J., Journal of the Chemical Society. Perkin transactions II, 1974, p. 88 - 93
  作者：Hamer,N.K.、Wills,A.J.

  DOI：——

  日期：——
• 1,4-Dimethyl-2,3-diphenylfulvene: A convenient precursor to heteroatom-substituted-1-methyl-2,5-dimethyl-3,4-diphenylcyclopentadienyl transition metal complexes
  作者：Jana Donovalova、Carl R. Jackson、Eric A. Mintz

  DOI：10.1016/0022-328x(95)06083-9

  日期：1996.4

  Reaction of 2,5-dimethyl-3,4-diphenylcyclopent-2-enone (1) with Ph(3)P=CH2 in THF gave 2,5-dimethyl-3,4-diphenylcyclopent-2-ene-1-ylidene (2) in 75% yield. Treatment of 2 with one equivalent of Br-2, followed by two equivalents of triethylamine gave 1,4-dimethyl-2,3-diphenylfulvene (3) in 60% overall yield. Treatment of 3 with LiCH3 and LiC6H5 followed by FeCl2 gave [eta(5)-1-CH3CH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2 and [eta(5)-1-C6H5CH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2, respectively, in good yield. Treatment of 3 with LiNHC(CH3)(3) and LiP(C6H5)(2) followed by FeCl2 gave [eta(5)-1-(CH3)(3)CNHCH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2 and [eta(5)-1-(C6H5)(2)PCH2-2,5-(CH3)(2)-3,4-(C6H5)(2)C-5]Fe-2, respectively, in good yield. Treatment of 3 with (R)-LiNHCH(CH3)C6H5 followed by FeCl2 gave the corresponding enantiomerically pure ferrocene complex (R,R)-[eta(5)-1-C6H5CH(CH3)NHCH2-2.5-(CH3)(2)- 3,4-(C6H5)(2)C-5]Fe-2 in 44% yield.