2,5-bis(diphenylmethylene)-3-cyclopentenone | 144760-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis(diphenylmethylene)-3-cyclopentenone
• 英文别名: 2,5-Dibenzhydrylidenecyclopent-3-en-1-one
• CAS: 144760-04-3
• 化学式: C₃₁H₂₂O
• 分子量: 410.515
• InChiKey: IBLOTPIUYKZYIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-bis(diphenylmethylene)-3-cyclopentenone 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-Benzhydrylidene-3a-methyl-8-phenyl-3,3a-dihydro-cyclopenta[a]indene
  参考文献：
  名称：

  3,5-Dimethylenecyclopentenyl ions. Syntheses and properties of tetraphenyl derivatives

  摘要：

  While 3,5-bis(diphenylmethylene)cyclopentenyl anion is substantially stable, the corresponding cation is unstable probably due to its favorable structure for an intramolecular cyclization.

  DOI：

  10.1016/s0040-4039(00)61100-0
• 作为产物：
  描述：

  2-diphenylmethyl-6,6-diphenylfulvene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以96%的产率得到2,5-bis(diphenylmethylene)-3-cyclopentenone
  参考文献：
  名称：

  3,5-Dimethylenecyclopentenyl ions. Syntheses and properties of tetraphenyl derivatives

  摘要：

  While 3,5-bis(diphenylmethylene)cyclopentenyl anion is substantially stable, the corresponding cation is unstable probably due to its favorable structure for an intramolecular cyclization.

  DOI：

  10.1016/s0040-4039(00)61100-0

文献信息

• 2,5-Bis(diphenylmethylene)-3-cyclopentenone: a solvent-dependent cobalt cluster mediated propargyl radical coupling process
  作者：John H Kaldis、Michael J McGlinchey

  DOI：10.1016/s0040-4039(02)00692-5

  日期：2002.5

  Protonation of (1,1-diphenyl-2-propyn-1-ol)Co-2(CO)(6) with HBF4 in dichloromethane generates the expected metal-stabilized propargyl cation, and also rearranges to give the tricobalt cluster Ph2C=CH-CCo3(CO)(9) 9. In contrast, use of THF as solvent affords the radical (Co-2(CO)(6))[HCdropC-CPh2.] 2, which dimerizes at the methyne position; subsequent cyclization and carbonylation yields 2,5-bis-(diphenylmethylene)-3-cyclopentenone 11. The products have been characterized by X-ray crystallography, and the scope and mechanism of the reaction are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.