1,1-dihydro-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene | 16059-00-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1-dihydro-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene
• 英文别名: 2,3,4,5-tetraphenyl-1-germa-2,4-cyclopentadiene；2,3,4,5-tetraphenyl-1-germacyclopentadiene；dihydrogermole；1,1-dihydro-2,3,4,5-tetraphenylgermole；Tetraphenylgerman；Tetraphenylgermol；2,3,4,5-tetraphenyl-1H-germole
• CAS: 16059-00-0
• 化学式: C₂₈H₂₂Ge
• 分子量: 431.073
• InChiKey: DVMLAWQLDQFHRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  29
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1-dihydro-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene 以 四氢呋喃 为溶剂， 生成 3-Cyclohexa-2,5-dien-1-yl-2,4,5-triphenyl-1-germacyclopenta-1,3,5-triene
  参考文献：
  名称：

  Lee, V. Ya.; Nosov, K. S.; Egorov, M. P., Russian Chemical Bulletin, 1995, vol. 44, p. 770 - 771

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-dichloro-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene 、 lithium aluminium tetrahydride 以 四氢呋喃 为溶剂， 以51%的产率得到1,1-dihydro-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene
  参考文献：
  名称：

  Syntheses of Oligometalloles by Catalytic Dehydrocoupling

  摘要：

  The dehydrocoupling polycondensation of dihydro(tetraphenyl)metalloles (M = Si or Ge) with 0.2 mol % H(2)PtCl(6)center dot xH(2)O and excess cyclohexene produces the respective oligometallole in high yield (> 80%), where every silicon or germanium atom of the oligomer backbone is part of a silole or germole ring. Slightly less reactive catalyst systems of 1 mol % of Wilkinson's catalyst, (RhCl(PPh(3))(3)), or Pd(PPh(3))(4) yield the respective oligometallole in good yield (similar to 60%). With these latter systems, and under less vigorous reflux conditions, the (tetraphenyl)silole dimer may be isolated in 40% yield. X-ray structural characterization of the dimer reveals a Si-Si bond length of 2.363(2) angstrom and an H-Si-Si-H torsion angle of 90(2)degrees. Using excess cyclohexene as a coreagent with RhCl(PPh(3))(3) increases the yield of oligomer and also eliminates dimer byproduct. The methyl-terminated dimer forms in the reaction between H(2)PtCl(6)center dot xH(2)O and methylhydro(tetraphenyl)silole, but not in the similar reaction with the Rh and Pd catalysts. The methyl-terminated dimer has a Si-Si bond length of 2.375(1) angstrom and an H-Si-Si-H torsion angle of 92.3(1)degrees. Additionally, the oligosilole may be prepared by placing 1:2 dihydrosilole/cyclohexene and I mol % Wilkinson's catalyst in an Emrys Optimizer microwave synthesizer for 2 h. The molecular weight (M(w)) of the oligometalloles ranges from 3000 to 7000. Even though the metallole possesses a secondary metalloid atom and contains bulky phenyl groups, polymerization may occur because the tetraphenylmetallole monomers have small angles at C-M-C (93.21 degrees on C-Si-C and 90.14 degrees on C-Ge-C), resulting in less steric hindrance at the metalloid center. Oligo(tetraphenyl)germole exhibits an absorption at 378 nm (is an element of = 5400 L/mol Ge(.)cm). The germole is photoluminescent in toluene solution, emitting blue-green light (498 nm, Phi = 0.01). The hydrogen-terminated silole dimer shows a similar UV-vis absorption at 372 nm (is an element of = 9600 L/mol(.)cm) and luminesces green at 506 nm (Phi = 0.007). The methyl-terminated dimer absorbs at 370 nm (is an element of = 11800 L/mol(.)cm) and luminesces blue at 468 nm (Phi = 0.004).

  DOI：

  10.1021/om0490886

文献信息

• Synthese und reaktionen einiger 1R,1R′,2,3,4,5-tetraphenyl-1-germacyclopentadiene
  作者：Peter Jutzi、Alfons Karl

  DOI：10.1016/s0022-328x(00)84612-4

  日期：1981.7

  The synthesis of some new 1R,1R′,2,3,4,5-tetraphenyl-1-germacyclopentadienes is described (R = R′ = ethyl (II), p-tolyl (III), p-dimethylaminophenyl (dap) (IV), pentafluorophenyl (V); R = Cl, R′ = p-tolyl (VI), dap (VII); R = H, R′ = p-tolyl (VIII), dap (IX)). The germanes VIII, IX, X (R′ = phenyl) and XV (R′ = H) react with n-butyllithium in the presence of trimethylchlorosilane nearly quantitatively

  描述了一些新的1R，1R'，2,3,4,5-四苯基-1-锗环戊二烯的合成（R = R'=乙基（II），对甲苯基（III），对二甲基氨基苯基（dap）（ IV），五氟苯基（V）； R = Cl，R'=对甲苯基（VI），dap（VII）； R = H，R'=对甲苯基（VIII），dap（IX））。在三甲基氯硅烷存在下，锗烷VIII，IX，X（R'=苯基）和XV（R'= H）与正丁基锂几乎定量地反应为甲硅烷基化的化合物XI，XII，XIII和XVI。结果表明，即使在-78℃下，中间的1-锂-1-锗环戊二烯也是不稳定的。
• Cycloaddition of dialkylgermoles: synthesis and structures of 2,2,3,3-tetracyano-1,4,5,6-tetraphenyl-7-germanorborn-5-enes
  作者：O. S. Maslennikova、K. S. Nosov、V. I. Faustov、M. P. Egorov、O. M. Nefedov、G. G. Aleksandrov、I. L. Eremenko、S. E. Nefedov

  DOI：10.1007/bf02495774

  日期：2000.7

  Cycloaddition reactions of 1,1-dicyclopropyl-2,3,4,5-tetraphenyl-1-germacyclopentadiene (3) with dehydrobenzene, tetracyanoethylene, cyclooctyne, or dimethyl acetylenedicarboxylate as well as of 1,1-dimethy-2,3,4,5-tetraphenyl-1-germacyclopentadiene (4) and 2,3,4,5-tetraphenyl-1-germacyclopentadiene (5) with tetracyanoethylene or cyclooctyne were studied. Diels—Alder adducts of germoles3, 4, and5 with

  1,1-二环丙基-2,3,4,5-四苯基-1-锗环戊二烯 (3) 与脱氢苯、四氰基乙烯、环辛炔或乙炔二甲酸二甲酯以及 1,1-二甲基-2,3,4 的环加成反应,5-四苯基-1-锗环戊二烯 (4) 和 2,3,4,5-四苯基-1-锗环戊二烯 (5) 与四氰基乙烯或环辛炔进行了研究。制备了 Diels-Gemoles3、4 和 5 与四氰基乙烯的阿尔德加合物。这些加合物的结构是通过 X 射线衍射分析建立的，并检查了它们的热和光化学稳定性。
• Syntheses of Oligometalloles by Catalytic Dehydrocoupling
  作者：Sarah J. Toal、Honglae Sohn、Lev N. Zakarov、W. Scott Kassel、James A. Golen、Arnold L. Rheingold、William C. Trogler

  DOI：10.1021/om0490886

  日期：2005.6.20

  The dehydrocoupling polycondensation of dihydro(tetraphenyl)metalloles (M = Si or Ge) with 0.2 mol % H(2)PtCl(6)center dot xH(2)O and excess cyclohexene produces the respective oligometallole in high yield (> 80%), where every silicon or germanium atom of the oligomer backbone is part of a silole or germole ring. Slightly less reactive catalyst systems of 1 mol % of Wilkinson's catalyst, (RhCl(PPh(3))(3)), or Pd(PPh(3))(4) yield the respective oligometallole in good yield (similar to 60%). With these latter systems, and under less vigorous reflux conditions, the (tetraphenyl)silole dimer may be isolated in 40% yield. X-ray structural characterization of the dimer reveals a Si-Si bond length of 2.363(2) angstrom and an H-Si-Si-H torsion angle of 90(2)degrees. Using excess cyclohexene as a coreagent with RhCl(PPh(3))(3) increases the yield of oligomer and also eliminates dimer byproduct. The methyl-terminated dimer forms in the reaction between H(2)PtCl(6)center dot xH(2)O and methylhydro(tetraphenyl)silole, but not in the similar reaction with the Rh and Pd catalysts. The methyl-terminated dimer has a Si-Si bond length of 2.375(1) angstrom and an H-Si-Si-H torsion angle of 92.3(1)degrees. Additionally, the oligosilole may be prepared by placing 1:2 dihydrosilole/cyclohexene and I mol % Wilkinson's catalyst in an Emrys Optimizer microwave synthesizer for 2 h. The molecular weight (M(w)) of the oligometalloles ranges from 3000 to 7000. Even though the metallole possesses a secondary metalloid atom and contains bulky phenyl groups, polymerization may occur because the tetraphenylmetallole monomers have small angles at C-M-C (93.21 degrees on C-Si-C and 90.14 degrees on C-Ge-C), resulting in less steric hindrance at the metalloid center. Oligo(tetraphenyl)germole exhibits an absorption at 378 nm (is an element of = 5400 L/mol Ge(.)cm). The germole is photoluminescent in toluene solution, emitting blue-green light (498 nm, Phi = 0.01). The hydrogen-terminated silole dimer shows a similar UV-vis absorption at 372 nm (is an element of = 9600 L/mol(.)cm) and luminesces green at 506 nm (Phi = 0.007). The methyl-terminated dimer absorbs at 370 nm (is an element of = 11800 L/mol(.)cm) and luminesces blue at 468 nm (Phi = 0.004).
• JUTZI P.; KARL A., J. ORGANOMETAL CHEM., 1981, 215, NO 1, 19-25
  作者：JUTZI P.、 KARL A.

  DOI：——

  日期：——
• Lee, V. Ya.; Nosov, K. S.; Egorov, M. P., Russian Chemical Bulletin, 1995, vol. 44, p. 770 - 771
  作者：Lee, V. Ya.、Nosov, K. S.、Egorov, M. P.、Nefedov, O. M.

  DOI：——

  日期：——