isodicyclopentadiene | 75725-33-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: isodicyclopentadiene
• 英文别名: tricyclo[5.2.1.0(2.6)]deca-2,5-diene；Tricyclo[5.2.1.02,6]deca-2(6),3-diene
• CAS: 75725-33-6
• 化学式: C₁₀H₁₂
• 分子量: 132.205
• InChiKey: NZZPSMDOMWOCST-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 12 Torr)
• 密度：
  0.9918 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  isodicyclopentadiene 生成 3-isocyclopentadiene
  参考文献：
  名称：

  PAQUETTE, L. A.;WILLIAMS, R. V.;CARR, R. V. C.;CHARUMILIND, P.;BLOUNT, J.+, J. ORG. CHEM., 1982, 47, N 23, 4566-4572

  摘要：

  DOI：
• 作为产物：
  描述：

  tetracyclo[6.2.1.12,5.01,6]dodec-6-ene-9,10-dione 生成 isodicyclopentadiene
  参考文献：
  名称：

  SUBRAMANYAM, R.;BARTLETT, P. D.;IGLESIAS, G. Y. M.;WATSON, W. H.;GALLOY, +, J. ORG. CHEM., 1982, 47, N 23, 4491-4498

  摘要：

  DOI：

文献信息

• Structure of lithium isodicyclopentadienide and lithium cyclopentadienide in tetrahydrofuran solution. A combined NMR, IGLO, and MNDO study
  作者：Leo A. Paquette、Walter Bauer、Mark R. Sivik、Michael Buehl、Martin Feigel、Paul v. R. Schleyer

  DOI：10.1021/ja00180a020

  日期：1990.11

  NMR shows lithium isodicyclopentadienide 1 to exist as a monomer-dimer equilibrium in tetrahydrofuran (THF) at low temperatures. In the monomer, a contact ion pair, lithium is located at the exo face (4). The dimer consists of lithium "sandwiched" between the exo faces of two anion moieties (6). The sandwiched lithium in 6 is highly shielded and resonates at -12.8 ppm. The experimental lithium chemical

  一维和二维 NMR 显示异二环戊二烯锂 1 在低温下在四氢呋喃 (THF) 中作为单体-二聚体平衡存在。在单体中，接触离子对，锂位于外表面 (4)。二聚体由“夹在”两个阴离子部分的外表面之间的锂组成 (6)。夹在 6 中的锂是高度屏蔽的，共振频率为 -12.8 ppm。IGLO 计算增强了实验锂化学位移。温度相关 6Li NMR 谱的线形分析揭示了两个动力学过程：(Li(THF)4)+ 与单体结合的锂的快速交换以及夹层和单体结合的锂之间的较慢交换。MNDO 计算证实了单体和二聚体 1 的外锂硫异构体与其内锂硫对应物的相对稳定性的 NMR 结果。此外，MNDO 预测接触离子对对单体和二聚体都有利。在室温下，单体 4-二聚体 6 的平衡明显向单体侧移动。这可能解释了早期的实验结果，即在 +25 0C 时主要是对 1 的外亲电攻击，而不是在 -78 6C 时的首选亲电攻击。发现环戊二烯锂 56 在
• BHIDE, VINAYAK;RINALDI, PETER;FARONA, MICHAEL F., J. ORGANOMET. CHEM., 376,(1989) N, C. 91-101
  作者：BHIDE, VINAYAK、RINALDI, PETER、FARONA, MICHAEL F.

  DOI：——

  日期：——
• Triple-Decker Complexes. 11. Triple-Decker Complexes as Intermediates in Cyclopentadienyl Transfer Reactions: Stereospecific Transfer of Isodicyclopentadienyl Ligands from Ruthenium to Rhodium
  作者：Gerhard E. Herberich、Ursula J. Jansen

  DOI：10.1021/om00002a034

  日期：1995.2

  The two diastereomers Cp*Ru(Idcp) (exo-8 and endo-8; Idcp = tricyclo[5.2.1.0(2.6)]deca-3,5-dien-2-yl) were synthesized from (Cp*RuCl)(4) and Li(Idcp) in THF, and exo-[Cp*Rh(Idcp)]-PF6 (exo-9(PF6)) was obtained from [Cp*Rh(OCMe(2))(3)](BF4)(2) and tricyclo[5.2.1.0(2.6)]deca-2,5-diene (IdcpH) in acetone, The structures of exo-8 and exo-9(PF6) were determined by X-ray diffraction, The ruthenocene derivatives 8 establish an isomerization equilibrium in the presence of a catalytic trace of [Cp*Ru(mu-Cp)RuCp*]CF3SO3 or of other sources of metalloelectrophiles[Cp*Ru(solv)(3)](+) (solv = Me(2)CO, MeCN); above -40 degrees C endo-8 is transformed into exo-8. Both isomers read with [Cp*Rh(OCMe(2))(3)](2+) in acetone to undergo an Idcp transfer reaction, thereby forming endo-9(+) with small admixtures of exo-9(+) and [Cp*Ru(OCMe(2))(3)](+) (7(+)), In the presence of naphthalene as quenching agent for 7(+), exo-8 gives endo-9(+) and endo-8 gives exo-9(+) with 100% stereoselectivity in both cases, Hence, the Idcp transfer reaction from Ru to Rh is stereospecific. The hypothetical triple-decker complexes [Cp*Ru-(mu-Idcp)RuCp*]+ (11(+)) and [Cp*Ru(mu-Idcp)RhCp*]2(+) (12a(2+) and 12b(2+)) are proposed as reaction intermediates for the isomerization and for the Idcp transfer reactions, respectively.