Mes2FlGeOGeFlMes2 | 132775-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Mes2FlGeOGeFlMes2
• 英文别名: [(trimethylphenyl)2Ge(fluorenyl)]2O；9H-fluoren-9-yl-[9H-fluoren-9-yl-bis(2,4,6-trimethylphenyl)germyl]oxy-bis(2,4,6-trimethylphenyl)germane
• CAS: 132775-05-4
• 化学式: C₆₂H₆₂Ge₂O
• 分子量: 968.354
• InChiKey: ZODWAPXVCOVSNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.93
• 重原子数：
  65.0
• 可旋转键数：
  8.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (mesityl)2Ge(fluorenylidene) 在 water 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以85%的产率得到Mes2FlGeOGeFlMes2
  参考文献：
  名称：

  来自胚芽的两种胚芽乙炔：形成和结构

  摘要：

  Dimesitylfluorenylidenegermane (1) reacts very readily with aldehydes and ketones, according to a [2 + 2] cycloaddition, leading to the corresponding germaoxetanes. These four-membered-ring heterocycles are quite stable, mainly due to the large steric hindrance of the substituents. In the case of acetone, reaction with the enolic form has been observed, followed by a germanotropic rearrangement. Germaoxetanes 3 (monoclinic, P2(1)/n, a = 12.668 (5) angstrom, b = 16.794 (6) angstrom, c = 14.600 (5) angstrom, beta = 90.25 (3)degrees, V = 3106 (2) angstrom 3, Z = 4, R = 0.0525) and 4 (monoclinic, P2(1)/c, a = 22.807 (5) angstrom, b = 17.713 (6) angstrom, c = 18.425 (4) angstrom, beta = 102.64 (2)degrees, V = 7263 (3) angstrom 3, Z = 8, R = 0.0697), obtained from benzaldehyde and benzophenone, have been characterized by X-ray diffraction methods and their data compared to those of the acyclic digermoxane 6 (triclinic, P1BAR, a = 13.002 (3), angstrom, b = 14.962 (2) angstrom, c = 16.094 (1) angstrom, alpha = 98.92 (1)degrees, beta = 95.90 (2)degrees, gamma = 114.52 (1)degrees, V = 2765 (1) angstrom 3, Z = 2, R = 0.0781) prepared by hydrolysis of germene 1.

  DOI：

  10.1021/om00052a024

文献信息

• The addition of terminal alkynes to dimesitylfluorenylidenegermane
  作者：Nada Y. Tashkandi、Laura C. Pavelka、Margaret A. Hanson、Kim M. Baines

  DOI：10.1139/cjc-2013-0532

  日期：2014.6

  A variety of terminal alkynes were added to dimesitylfluorenylidenegermane, Mes₂Ge=CR₂ (where CR₂ = fluorenylidene). The addition of phenylacetylene and 1-hexyne to Mes₂Ge=CR₂ gave a germacyclohexene via a cycloaddition where the germene acts as the 4π component and the alkyne as the 2π component. Through the use of a mechanistic probe, trans-(2-phenylcyclopropyl)-acetylene, the reaction was postulated to proceed through a concerted [2+4] cycloaddition. The addition of ethoxyacetylene to the germene produced both a [2+2] cycloadduct, a germacyclobutene, and a [2+4] cycloadduct, a germacyclohexene. The results of this study are compared to the results of the addition of alkynes to Mes₂Ge=CHCH₂-t-Bu.

  将各种末端炔烃加入二间苯基芴亚基锗烯，Mes₂Ge=CR₂（其中CR₂ = 芴亚基）。苯基乙炔和1-己炔加入到Mes₂Ge=CR₂中，通过环加成反应形成了一种锗环己烯，其中锗烯充当4π组分，炔烃充当2π组分。通过使用一个机械探针，反式-(2-苯基环丙基)-乙炔，推测该反应通过一个协同的[2+4]环加成进行。将乙氧基乙炔加入到锗烯中产生了一个[2+2]环加成产物，一种锗环丁烯，以及一个[2+4]环加成产物，一种锗环己烯。这项研究的结果与将炔烃加入到Mes₂Ge=CHCH₂-t-Bu的结果进行了比较。
• Reactivity of dimesitylfluorenylidenegermane with unsaturated nitrogen compounds
  作者：M. Lazraq、J. Escudie、C. Couret、J. Satge、M. Soufiaoui

  DOI：10.1021/om00050a054

  日期：1991.4

  Dimesitylfluorenylidenegermane (1) reacts with ethylbenzylideneamine (PhCH = NEt) to give, according to a [2 + 2] cycloaddition, the very thermally stable four-membered-ring germaazetidine 2. In contrast, imines with a NH function, such as (diphenylmethylidene)amine (Ph2C = NH), react only as protic reagents. A [2 + 4] cycloaddition is observed with azobenzene, affording 5, which slowly aromatizes to 6 or thermally rearranges to give the [2 + 2] cycloadduct germadiazetidine 7. In the case of nitrosobenzene, only the germanone dimer 17 and imine 9 have been observed, probably via the preliminary formation of transient four-membered heterocycle 15.
• Addition of Aldehydes to Germenes: The Influence of Solvent
  作者：Christopher J. Allan、Crispin R. W. Reinhold、Laura C. Pavelka、Kim M. Baines

  DOI：10.1021/om200114n

  日期：2011.6.13

  The addition of trans-(2-phenylcyclopropyl)carboxaldehyde to dimesitylfluorenylidenegermane produced four diastereomers of a 1,2-oxagermin, 7a-d, 2,2,4,4-tetramesityl-1,3-dioxadigermetane (8), and fluorenylidene-(trans-2-phenylcyclopropyl)methane (9). The ratio of the products showed a strong dependence on the solvent: 7a-d were formed almost exclusively when ether or benzene was used as the solvent for the reaction, whereas 1,3-dioxadigermetane 8 and alkene 9 were the major products formed in THF. A mechanism is proposed to account for the observations.