1,3-diphenyl-4H-cyclopenta[c]thiophene | 869729-32-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,3-diphenyl-4H-cyclopenta[c]thiophene
• 英文别名: 1,3-diphenyl-6H-cyclopenta[c]thiophene
• CAS: 869729-32-8
• 化学式: C₁₉H₁₄S
• 分子量: 274.386
• InChiKey: JKIAECXFZFTRBR-UHFFFAOYSA-N

物化性质

• 熔点：
  80-83 °C(Solv: methanol (67-56-1))
• 沸点：
  448.6±45.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-diphenyl-4H-cyclopenta[c]thiophene 、 五羰基溴化锰(I) 在 n-BuLi 、 Me₃SnCl 作用下， 以 not given 为溶剂， 以90%的产率得到tricarbonyl(η5-1,3-diphenylcyclopenta[c]thienyl)manganese
  参考文献：
  名称：

  Synthesis, Characterization, and Structure of Cyclopenta[c]thiophenes and Their Manganese Complexes

  摘要：

  1,3-Diaryl-4H-cyclopenta[c]thiophenes are efficiently prepared from 1,2-diaroylcyclopentadienes by use of Lawesson's reagent. eta5-Cyclopenta[c]thienyl complexes, [Mn(eta5-SC7H3-1,3-R2)(CO)3] (R = Me, Ph), are prepared in high yield by ligand substitution reactions of [MnBr(CO)5] with [SnMe3(SC7H3-1,3-R2)]. Alternatively, thiation with P4S10/NaHCO3 converts [Mn{eta5-1,2-C5H3(COR)2)(CO)3] to [Mn(eta5-SC7H3-1,3-R2)(CO)3] (R = Ph, 4-tolyl, 4-MeOC6H4, benzo[2,3-b]thienyl). The molecular structures of complexes with R = Me, Ph show planar eta5-cyclopenta[c]thienyl ligands, with the manganese atom slightly displaced away from the ring-fusion bond.

  DOI：

  10.1021/ja054513n
• 作为产物：
  描述：

  1-benzoyl-6-phenyl-6-hydroxypentafulvene 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以22.5%的产率得到1,3-diphenyl-4H-cyclopenta[c]thiophene
  参考文献：
  名称：

  Synthesis, Characterization, and Structure of Cyclopenta[c]thiophenes and Their Manganese Complexes

  摘要：

  1,3-Diaryl-4H-cyclopenta[c]thiophenes are efficiently prepared from 1,2-diaroylcyclopentadienes by use of Lawesson's reagent. eta5-Cyclopenta[c]thienyl complexes, [Mn(eta5-SC7H3-1,3-R2)(CO)3] (R = Me, Ph), are prepared in high yield by ligand substitution reactions of [MnBr(CO)5] with [SnMe3(SC7H3-1,3-R2)]. Alternatively, thiation with P4S10/NaHCO3 converts [Mn{eta5-1,2-C5H3(COR)2)(CO)3] to [Mn(eta5-SC7H3-1,3-R2)(CO)3] (R = Ph, 4-tolyl, 4-MeOC6H4, benzo[2,3-b]thienyl). The molecular structures of complexes with R = Me, Ph show planar eta5-cyclopenta[c]thienyl ligands, with the manganese atom slightly displaced away from the ring-fusion bond.

  DOI：

  10.1021/ja054513n

文献信息

• Synthesis, Characterization, and Structure of Cyclopenta[<i>c</i>]thiophenes and Their Manganese Complexes
  作者：Chad A. Snyder、John P. Selegue、Nathan C. Tice、Chad E. Wallace、Mark T. Blankenbuehler、Sean Parkin、Keith D. E. Allen、Ryan T. Beck

  DOI：10.1021/ja054513n

  日期：2005.11.1

  1,3-Diaryl-4H-cyclopenta[c]thiophenes are efficiently prepared from 1,2-diaroylcyclopentadienes by use of Lawesson's reagent. eta5-Cyclopenta[c]thienyl complexes, [Mn(eta5-SC7H3-1,3-R2)(CO)3] (R = Me, Ph), are prepared in high yield by ligand substitution reactions of [MnBr(CO)5] with [SnMe3(SC7H3-1,3-R2)]. Alternatively, thiation with P4S10/NaHCO3 converts [Mneta5-1,2-C5H3(COR)2)(CO)3] to [Mn(eta5-SC7H3-1,3-R2)(CO)3] (R = Ph, 4-tolyl, 4-MeOC6H4, benzo[2,3-b]thienyl). The molecular structures of complexes with R = Me, Ph show planar eta5-cyclopenta[c]thienyl ligands, with the manganese atom slightly displaced away from the ring-fusion bond.