1,1',2,2',3,3'-六苯基-1,1'-联(2-环丙烯) | 4997-62-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 中文名称: 1,1',2,2',3,3'-六苯基-1,1'-联(2-环丙烯)
• 英文名称: hexaphenyl-[3,3']bicycloprop-1-enyl
• 英文别名: 3,3'-Bis-(triphenylcyclopropenyl)；Bis-triphenylcyclopropenyl；Bistriphenylcyclopropenyl；Benzene, 1,1',1'',1''',1'''',1'''''-(bi-2-cyclopropen-1-yl)-1,1',2,2',3,3'-hexaylhexakis-；[2,3-diphenyl-1-(1,2,3-triphenylcycloprop-2-en-1-yl)cycloprop-2-en-1-yl]benzene
• CAS: 4997-62-0
• 化学式: C₄₂H₃₀
• 分子量: 534.7
• InChiKey: DQELQSOUCKXCIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  1,1',2,2',3,3'-六苯基-1,1'-联(2-环丙烯) 生成 六苯基苯
  参考文献：
  名称：

  THE SYNTHESIS OF BIS-TRIPHENYLCYCLOPROPENYL, AN UNDISSOCIATED DIMER OF THE TRIPHENYLCYCLOPROPENYL RADICAL, AND ITS ISOMERIZATION TO HEXAPHENYLBENZENE

  摘要：

  DOI：

  10.1021/ja01526a077
• 作为产物：
  描述：

  1,2,3-triphenylcyclopropenyl-3-ium tetrafluoroborate 在 chromium dichloride 作用下， 以 盐酸 为溶剂， 生成 1,1',2,2',3,3'-六苯基-1,1'-联(2-环丙烯)
  参考文献：
  名称：

  碳正离子的单电子还原。V. 用 Cr(II) 还原取代的环丙烯离子的动力学研究

  摘要：

  一系列苯基和/或正丙基取代的环丙烯鎓离子与 Cr(II) 的单电子还原已在 10% HCl 溶液中进行。三苯基环丙烯 (Ia)、二苯基-正-丙基环丙烯 (Ib) 和苯基二-正-丙基环丙烯 (Ic) 离子的还原定量得到各自环丙烯基的二聚体，即双（环丙烯基）衍生物，而三-n -丙基环丙烯鎓离子 (Id) 非常不活泼。动力学研究表明，这些稳定的碳正离子对单电子还原剂（Cr（II））的反应性随着苯基取代基数量的减少而降低：k225°C=3.0×10-4l/g- Ia 为 ion·s，Ib 为 2.7×10-6l/g-ion·s，Ic 为 2.8×10-9l/g-ion·s，Id 为 <10-11l/g-ion·s。发现添加的 NaCl 会加速 Ia 的还原速率，而添加的 HCl 显示出初始速率增强效应，随后是轻微的速率延迟效应。logk2 与相应阳离子的电子亲和力的关系图，估计...

  DOI：

  10.1246/bcsj.46.3881

文献信息

• The One-Electron Reduction of Carbonium Ions. V. A Kinetic Study on the Reduction of the Substituted Cyclopropenium Ions with Cr(II)
  作者：Kunio Okamoto、Koichi Komatsu、Akira Hitomi

  DOI：10.1246/bcsj.46.3881

  日期：1973.12

  cyclopropenium ions with Cr(II) has been carried out in a 10% HCl solution. The reduction of triphenylcyclopropenium (Ia), diphenyl-n-propylcyclopropenium (Ib), and phenyldi-n-propylcyclopropenium (Ic) ions quantitatively gives dimers of the respective cyclopropenyl radicals, i.e., the bis(cyclopropenyl) derivatives, whereas the tri-n-propylcyclopropenium ion (Id) is quite unreactive. A kinetic study has shown

  一系列苯基和/或正丙基取代的环丙烯鎓离子与 Cr(II) 的单电子还原已在 10% HCl 溶液中进行。三苯基环丙烯 (Ia)、二苯基-正-丙基环丙烯 (Ib) 和苯基二-正-丙基环丙烯 (Ic) 离子的还原定量得到各自环丙烯基的二聚体，即双（环丙烯基）衍生物，而三-n -丙基环丙烯鎓离子 (Id) 非常不活泼。动力学研究表明，这些稳定的碳正离子对单电子还原剂（Cr（II））的反应性随着苯基取代基数量的减少而降低：k225°C=3.0×10-4l/g- Ia 为 ion·s，Ib 为 2.7×10-6l/g-ion·s，Ic 为 2.8×10-9l/g-ion·s，Id 为 <10-11l/g-ion·s。发现添加的 NaCl 会加速 Ia 的还原速率，而添加的 HCl 显示出初始速率增强效应，随后是轻微的速率延迟效应。logk2 与相应阳离子的电子亲和力的关系图，估计...
• Metal-Catalyzed Cyclopropene Rearrangements for Benzannulation: Evaluation of an Anthraquinone Synthesis Pathway and Reevaluation of the Parallel Approach via Carbene-Chromium Complexes
  作者：M. F. Semmelhack、Suzzy Ho、D. Cohen、M. Steigerwald、M. C. Lee、G. Lee、Adam M. Gilbert、William D. Wulff、Richard G. Ball

  DOI：10.1021/ja00095a014

  日期：1994.8

  The reaction of 3-arylcyclopropenes with Cr(CO)(6) and Mo(CO)(6) produces naphthols, in an example of metal-promoted benzannulation. Substituents at C-3 (in addition to aryl) have a strong effect on the success of the process: 3-H derivatives are generally effective, but the yields decrease for 3-alkyl derivatives as the size of the alkyl group increases. The 3,3-diphenyl and 3-cyano derivatives are unreactive. The mechanism is postulated to involve metal-complexed vinyl carbene units, parallel with the benzannulation reaction involving arylcarbene complexes with alkynes. The regioselectivity has been probed with various unsymmetrically 1,2-disubstituted 3-arylcyclopropenes. The results suggest a simple correlation with steric size, consistent with initial cleavage of the cyclopropene sigma bond bearing the smaller substituent. The result of this regioselectivity is a product structure showing a substituent arrangement opposite to that from the carbene-chromium approach; the smaller substituent of the cyclopropyl double bond ends up adjacent to the phenol OH in the product. Catalytic activity at low efficiency was observed, using a Mo(CO)a catalyst. However, the use of Mo(CO)(6) also promotes formation of indenes as significant byproducts at the expense of naphthalenes. Attempts to use the arylcyclopropene rearrangement to convert a 3-(1,4-dimethoxy-2-naphthyl)cyclopropene to an anthraquinone skeleton produced instead a phenanthrene via an unusual substitution for a methoxy substituent. A related example previously reported to produce anthraquinones via the naphthylcarbene-chromium/ alkyne reaction was shown to be in error; the correct structure is again a phenanthrone, and the product is exactly parallel with that observed in the cyclopropene rearrangement. A naphthoquinone substituted with a cyclopropene at C-2 does provide the first example of metal-promoted benzannulation to give an anthraquinone.
• THE SYNTHESIS OF BIS-TRIPHENYLCYCLOPROPENYL, AN UNDISSOCIATED DIMER OF THE TRIPHENYLCYCLOPROPENYL RADICAL, AND ITS ISOMERIZATION TO HEXAPHENYLBENZENE
  作者：Ronald Breslow、Peter Gal

  DOI：10.1021/ja01526a077

  日期：1959.9
• Isomerization of Biscyclopropenyls to Benzenes^1,2
  作者：Ronald Breslow、Peter Gal、Hai Won Chang、L. J. Altman

  DOI：10.1021/ja00950a028

  日期：1965.11
• Gompper,R. et al., Chemische Berichte, 1979, vol. 112, p. 218 - 233
  作者：Gompper,R. et al.

  DOI：——

  日期：——

表征谱图