5-(5H-dibenzo[a,d]cycloheptene-5-ylidene)-5H-dibenzo[a,d]cycloheptene | 19301-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 5-(5H-dibenzo[a,d]cycloheptene-5-ylidene)-5H-dibenzo[a,d]cycloheptene
• 英文别名: 5,5'-bi(dibenzo[a,d]cyclohepten-5-ylidene)；[5,5']bi[dibenzo[a,d]cycloheptenylidene]；[5,5']Bi(dibenzo[a,d]cycloheptenyliden)；Δ^5,5'-Bis-5H-dibenzocyclohepten, 2,3;6,7;2',3';6',7'-Tetrabenzoheptafulvalen；anti-2.3,6.7,2'.3',6'.7'-Tetrabenzoheptafulvalen；syn-2.3,6.7,2'.3',6'.7'-Tetrabenzoheptafulvalen；5,5'-Bi-(5h-dibenzo[a,d]cyclohepten-5-ylidene)；2-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene
• CAS: 19301-89-4；25689-65-0；25689-66-1
• 化学式: C₃₀H₂₀
• 分子量: 380.489
• InChiKey: DIEUEXQHCNAGGH-UHFFFAOYSA-N

物化性质

• 熔点：
  324 °C
• 沸点：
  541.2±50.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  5-(5H-dibenzo[a,d]cycloheptene-5-ylidene)-5H-dibenzo[a,d]cycloheptene 在 磺酰氯 、 五氟化锑 作用下， 生成
  参考文献：
  名称：

  Antiaromaticity in Fluorenylidene Dications. Experimental and Theoretical Evidence for the Relationship between the HOMO/LUMO Gap and Antiaromaticity

  摘要：

  The relationship between the calculated energy of the HOMO-LUMO gap, where (epsilon(LUMO) - epsilon(HOMO))/2 is defined as Delta(HL), and of the longest wavelength transition in the UV-visible spectrum, DeltaE, was examined for a series of aromatic and antiaromatic cations and dications. TD-DFT calculations accurately modeled the energies of a series of dications including fluorenylidene dications whose UV-visible spectra are reported, as well as the energies of a series of aromatic and antiaromatic monocations whose spectra were previously reported. There is a linear correlation of the energy of the longest wavelength transition, DeltaE(calc), with Delta(HL). There is no linear relationship between DeltaE(calc) and the sum of the NICS values, but there is a linear relationship between DeltaE(calc) multiplied by the number of atoms in the conjugated system, DeltaE(calc(T)), and the sum of the NICS values. There is also an approximate linear relationship between the average H-1 NMR shift and the sum of the NICS values. These relationships give further support to the suggestion that the magnetic and energetic criteria of aromaticity and antiaromaticity are related. Furthermore, the data suggest that species that have DeltaE(calc(T)) < 20 are antiaromatic whereas those with DeltaE(calc(T)) > 30 are aromatic.

  DOI：

  10.1021/jo0499266
• 作为产物：
  描述：

  5-二苯并环庚烯酮 在 盐酸 、 amalgamated zinc 、 甲苯 作用下， 生成 5-(5H-dibenzo[a,d]cycloheptene-5-ylidene)-5H-dibenzo[a,d]cycloheptene
  参考文献：
  名称：

  Treibs; Klinkhammer, Chemische Berichte, 1951, vol. 84, p. 671,679

  摘要：

  DOI：

文献信息

• Cage Hydrocarbons Derived from Dibenzosuberenone
  作者：Marcus Pillekamp、Wasim Alachraf、Iris M. Oppel、Gerald Dyker

  DOI：10.1021/jo9018057

  日期：2009.11.6

  The reinvestigation of the synthesis of the fascinating cage compound 2 reveals an incorrect structure of photodimer 2, as well as of the putatively isolated intermediate 9. These products have to be reassigned as monomeric pyramidalized alkene 3 and spirocyclic dichloride 10, respectively.

  对令人着迷的笼状化合物2的合成进行的重新研究显示，光二聚体2以及推定的中间体9的结构不正确。这些产物必须分别重新分配为单体金字塔形的烯烃3和螺环二氯化物10。
• Bergmann et al., Bulletin de la Societe Chimique de France, 1951, p. 669,680
  作者：Bergmann et al.

  DOI：——

  日期：——
• Schoenberg,A. et al., Chemische Berichte, 1969, vol. 102, p. 1453 - 1467
  作者：Schoenberg,A. et al.

  DOI：——

  日期：——
• AGRANAT, ISRAEL;COHEN, SHMUEL;ISAKSSON, ROLAND;SANDSTROM, JAN;SUISSA, M. +, J. ORG. CHEM., 55,(1990) N6, C. 4943-4950
  作者：AGRANAT, ISRAEL、COHEN, SHMUEL、ISAKSSON, ROLAND、SANDSTROM, JAN、SUISSA, M. +

  DOI：——

  日期：——