(phenylacetylenyl)triethoxygermane | 489433-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (phenylacetylenyl)triethoxygermane
• 英文别名: (triethoxygermyl)phenylacetylene；PhCCGe(OEt)3；Triethoxy(phenylethynyl)germane；triethoxy(2-phenylethynyl)germane
• CAS: 489433-02-5
• 化学式: C₁₄H₂₀GeO₃
• 分子量: 308.901
• InChiKey: OSWUBXDGRQXWOU-UHFFFAOYSA-N

物化性质

• 沸点：
  299.1±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (phenylacetylenyl)triethoxygermane 、 2-[bis(2-hydroxyethyl)amino]-1,1-diphenyl-1-ethanol 以 苯 为溶剂， 以76%的产率得到N(CH2CH2O)2(CH2CPh2O)GeCCPh
  参考文献：
  名称：

  三种具有两个苯基团的 1-苯基乙炔基锗烷的 X 射线衍射研究

  摘要：

  摘要 treo-N(CH2CH2O)2(CHPhCHPhO)GeC CPh (1), erythro-N(CH2CH2O)2(CHPhCHPhO)GeC CPh (2) 和 N(CH2CH2O)2(CH2CPh2O)GeC CPh (3) 的单晶结构由 X 射线衍射研究确定。这些化合物表现出跨环的 N→Ge 相互作用；这种相互作用的强度取决于 Ph 基团在 atrane 骨架中的位置 (1, d(N→Ge)=2.210(4) A; 2, d(N→Ge)=2.166(4) A; 3, d(N) →Ge)=2.138(3) A)。这些化合物的结构与执行的 DFT 计算数据一起讨论。综述了在 atrane 骨架中含有碳取代基的 14 族元素 (Si, Ge) 金属特拉烷的分子结构的一般趋势。

  DOI：

  10.1016/j.molstruc.2004.12.025
• 作为产物：
  描述：

  乙醇 、 trichlorogermylphenylacetylene 在 Et₃N 作用下， 以 乙醚 、 乙醇 为溶剂， 以94%的产率得到(phenylacetylenyl)triethoxygermane
  参考文献：
  名称：

  Synthesis and Crystal Structure of the Germatrane E-N(CH)₂CH₂O₃GeC(Br)=C(Br)Ph

  摘要：

  (苯基乙炔基)三乙氧基锗烷，(EtO)3GeC≡CPh（3），在CHCl3/CCl4溶液中与溴反应，生成Z-和E-的(EtO)3GeC(Br)=C(Br)Ph（4）混合物，Z/E比为3/1。用N(CH2CH2OH)3处理该产物得到Z-和EN(CH2CH2O)3GeC(Br)=C(Br)Ph（2）的混合物，收率很高。E-2化合物收率为16%。所有新化合物的分子组成和结构都通过元素分析，1H和13C NMR光谱确定。E-2的晶体结构已报告。讨论了DFT计算在3和N(CH2CH2O)3GeC≡CPh（1）溴化产物中不同Z/E比率的可能原因。

  DOI：

  10.1515/znb-2003-0703

文献信息

• Synthesis and characterization of 3- and 4-phenylgermatranes: X-ray crystal structures of N(CH2CH2O)2(CH2CHPhO)GeZ (Z=F, OSiMe3, CCPh) and N(CH2CH2O)2(CHPhCH2O)GeOH
  作者：Ekaterina V. Gauchenova、Sergey S. Karlov、Anastasia A. Selina、Eleonora S. Chernyshova、Andrei V. Churakov、Judith A.K. Howard、Nikolaj A. Troitsky、Stanislav N. Tandura、Jörg Lorberth、Galina S. Zaitseva

  DOI：10.1016/s0022-328x(03)00225-0

  日期：2003.6

  Reaction of excess of product A [(HOCH2CH2)(2)NCH2CH(Ph)OH (1):(HOCH2CH2)(2)NCH(Ph)CH2OH (2) = 9:1] with GeCl4 led to a mixture of 1-chloro-3-phenylgermatrane (3) and 1-chloro-4-phenylgermatrane (4). Compound 4 was isolated in yield 9% from this mixture. Reaction of (EtO)(3)GeCl with product A gave 3 in yield 55%. 1-(Phenylethynyl)-3-phenylgermatrane (5) was prepared in yield 31% by treatment of (EtO)(3)GeCdropCPh with product A. Reaction of product A with mixture of GeO2 and H2O produced N(CH2CH2O)(2)(CH2CHPhO)GeOH (6) in yield 73%. The presence of N(CH2CH2O)(2)(CHPhCH2O)GeOH (7) among the products of this reaction was confirmed by H-1-, C-13-NMR spectroscopy and X-ray analysis. N(CH2CH2O)(2)(CH2CHPhO)GeF (8) is formed by the treatment of 6 with BF3 . Et2O. N(CH2CH2O)(2)(CH2CHPhO)GeOSiMe3 (9) was obtained by silylation of 6 with (Me3Si)(2)NH or Me3SiCl-Et3N. Refluxing of a suspension of 6 in xylene with continuous removal of water by azeotropic distillation afforded [N(CH2CH2O)(2)(CH(2)CHPh0)Ge](2)O (10). 9 reacted with SOCl2, Me3SiBr and Me3SiOTf to give N(CH2CH2O)(2)(CH2CHPhO)GeX (3, X = Cl; 11, X = Br; 12, X = OTf), respectively. Reaction of 11 with Et3SnOMe led to the formation of N(CH2CH2O)(2)(CH2CHPhO)GeO e (13). Germatranes N(CH2CH2O)(2)(CH2CHPhO)GeY [14, Y = Flu (fluorenyl); 15, Y = N(SiMe3)(2)] were obtained from the nucleophilic substitution of the substituent X in N(CH2CH2O)(2)(CH2CHPhO)GeX (X = OSiMe3, Br) with the corresponding LiY. All compounds were characterized by H-1- and C-13-NMR spectroscopy and mass spectrometry. Single-crystal structures of 5 and 7-9 were determined by X-ray diffraction studies. (C) 2003 Elsevier Science B.V. All rights reserved.
• Synthesis and Crystal Structure of the Germatrane E-N(CH)₂CH₂O₃GeC(Br)=C(Br)Ph
  作者：Anastasia A. Selina、Sergey S. Karlova、Klaus Harms、Daniil A. Tyurina、Yuri F. Oprunenko、Jörg Lorberth、Galina S. Zaitseva

  DOI：10.1515/znb-2003-0703

  日期：2003.7.1

  The reaction of (phenylacetylenyl)triethoxygermane, (EtO)₃GeC≡CPh (3), with bromine in CHCl₃/CCl₄ solution leads to a mixture of Z- and E- (EtO)₃GeC(Br)=C(Br)Ph (4) in the ratio Z/E = 3/1. Treatment of this product with N(CH₂CH₂OH)3 affords a mixture of Z- and EN(CH₂CH₂O)₃GeC(Br)=C(Br)Ph (2) in high yield. Compound E-2 was isolated in 16% yield. The molecular composition and the structure of all new compounds have been established by elemental analyses, ¹H and ¹³C NMR spectroscopy. The crystal structure of E-2 is reported. The possible reasons for the different Z/E ratios in the products of the bromination of 3 and N(CH₂CH₂O)₃GeC≡CPh (1) are discussed using DFT calculations.

  (苯基乙炔基)三乙氧基锗烷，(EtO)3GeC≡CPh（3），在CHCl3/CCl4溶液中与溴反应，生成Z-和E-的(EtO)3GeC(Br)=C(Br)Ph（4）混合物，Z/E比为3/1。用N(CH2CH2OH)3处理该产物得到Z-和EN(CH2CH2O)3GeC(Br)=C(Br)Ph（2）的混合物，收率很高。E-2化合物收率为16%。所有新化合物的分子组成和结构都通过元素分析，1H和13C NMR光谱确定。E-2的晶体结构已报告。讨论了DFT计算在3和N(CH2CH2O)3GeC≡CPh（1）溴化产物中不同Z/E比率的可能原因。
• X-ray diffraction studies of three 1-phenylethynylgermatranes with two phenyl groups in atrane skeleton
  作者：Sergey S. Karlov、Anastasia A. Selina、Eleonora S. Chernyshova、Maxim V. Zabalov、Andrei V. Churakov、Judith A.K. Howard、Victor A. Tafeenko、Galina S. Zaitseva

  DOI：10.1016/j.molstruc.2004.12.025

  日期：2005.4

  166(4) A; 3, d(N→Ge)=2.138(3) A). The structures of these compounds are discussed along with performed DFT calculations data. General trends for molecular structures of the group 14 elements (Si, Ge) metallatranes containing carbon substituents in atrane framework are reviewed.

  摘要 treo-N(CH2CH2O)2(CHPhCHPhO)GeC CPh (1), erythro-N(CH2CH2O)2(CHPhCHPhO)GeC CPh (2) 和 N(CH2CH2O)2(CH2CPh2O)GeC CPh (3) 的单晶结构由 X 射线衍射研究确定。这些化合物表现出跨环的 N→Ge 相互作用；这种相互作用的强度取决于 Ph 基团在 atrane 骨架中的位置 (1, d(N→Ge)=2.210(4) A; 2, d(N→Ge)=2.166(4) A; 3, d(N) →Ge)=2.138(3) A)。这些化合物的结构与执行的 DFT 计算数据一起讨论。综述了在 atrane 骨架中含有碳取代基的 14 族元素 (Si, Ge) 金属特拉烷的分子结构的一般趋势。