1,1-diethynyl-1-stannacyclohexane | 179804-65-0

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 1,1-diethynyl-1-stannacyclohexane
• 英文别名: 1,1-Diethynylstanninane
• CAS: 179804-65-0
• 化学式: C₉H₁₂Sn
• 分子量: 238.904
• InChiKey: JDGRLPLMHRCHLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-diethynyl-1-stannacyclohexane 以 氘代甲苯 为溶剂， 生成 2,3-diethyl-4-(ethoxyethylboryl)-1-trimethylstannyl-5-stannaspiro[4,5]dec-2-ene
  参考文献：
  名称：

  Stannacyclohexanes and spiro-tin compounds with s stannole or a stannolene group

  摘要：

  1,1-Diethynyl-1-stannacyclohexane (5) was prepared, and its reaction with triethylborane or 9-isobutyl-9-borabicyclo[3.3.1]nonane gave the corresponding spiro-tin compounds 6 and 7 with a stannole fragment, The molecular structure of the derivative 7 was determined by X-ray analysis (triclinic, space group P (1) over bar; a = 835.2(7), b = 1117.5(2), c = 1165.6(2) pm; alpha = 72.05(3), beta = 74.32(3), gamma = 50.61(3)degrees). Treatment of 6 with trimethyltin ethoxide gave at first quantitatively the spiro-tin compound 8 with a 2-stannolene unit which rearranges upon heating into the spiro-tin compound 9 with a 3-stannolene unit, The reaction of 7 with trimethyltin butoxide gave quantitatively another tetracyclic compound 10, analogous to 8, All compounds were characterised by H-1, B-11, C-13 and Sn-119 NMR data. Numerous coupling signs (n)J((SnH)-Sn-119-H-1) and (n)J((SnC)-Sn-119-C-13) and (2)J((SnSn)-Sn-119-Sn-117) were determined by 2D(13)C/H-1 and Sn-119/H-1 heteronuclear shift correlations. Compound 7 was studied by solid-state C-13 and Sn-119 CPMAS NMR. This revealed the presence of a second crystalline phase in the bulk of the solid material, as confirmed by powder X-ray diffraction data. Sn-119 CPMAS NMR spectra of 7 show resolved scalar Sn-119-B-11 coupling ((3)J((SnB)-Sn-119-B-11) = 68 +/- 5 and 65 +/- 5 Hz).

  DOI：

  10.1016/0022-328x(96)06162-1
• 作为产物：
  描述：

  1,1-dibromo-1-stannacyclohexane 、 乙炔基溴化镁 以 四氢呋喃 为溶剂， 以39.8%的产率得到1,1-diethynyl-1-stannacyclohexane
  参考文献：
  名称：

  Stannacyclohexanes and spiro-tin compounds with s stannole or a stannolene group

  摘要：

  1,1-Diethynyl-1-stannacyclohexane (5) was prepared, and its reaction with triethylborane or 9-isobutyl-9-borabicyclo[3.3.1]nonane gave the corresponding spiro-tin compounds 6 and 7 with a stannole fragment, The molecular structure of the derivative 7 was determined by X-ray analysis (triclinic, space group P (1) over bar; a = 835.2(7), b = 1117.5(2), c = 1165.6(2) pm; alpha = 72.05(3), beta = 74.32(3), gamma = 50.61(3)degrees). Treatment of 6 with trimethyltin ethoxide gave at first quantitatively the spiro-tin compound 8 with a 2-stannolene unit which rearranges upon heating into the spiro-tin compound 9 with a 3-stannolene unit, The reaction of 7 with trimethyltin butoxide gave quantitatively another tetracyclic compound 10, analogous to 8, All compounds were characterised by H-1, B-11, C-13 and Sn-119 NMR data. Numerous coupling signs (n)J((SnH)-Sn-119-H-1) and (n)J((SnC)-Sn-119-C-13) and (2)J((SnSn)-Sn-119-Sn-117) were determined by 2D(13)C/H-1 and Sn-119/H-1 heteronuclear shift correlations. Compound 7 was studied by solid-state C-13 and Sn-119 CPMAS NMR. This revealed the presence of a second crystalline phase in the bulk of the solid material, as confirmed by powder X-ray diffraction data. Sn-119 CPMAS NMR spectra of 7 show resolved scalar Sn-119-B-11 coupling ((3)J((SnB)-Sn-119-B-11) = 68 +/- 5 and 65 +/- 5 Hz).

  DOI：

  10.1016/0022-328x(96)06162-1

文献信息

• 1,1-Carboboration of Dialkynyltin Compounds using Tri­organoboranes of Greatly Different Lewis Acid Strength. 1,4-Stannabora-cyclohexa-2,5-dienes and Characterization of Zwitterionic Intermediates
  作者：Bernd Wrackmeyer、Peter Thoma、Simone Marx、Germund Glatz、Rhett Kempe

  DOI：10.1002/zaac.201300007

  日期：2013.6

  stannoles with diethynyltin compounds, whereas the strongly electrophilic B(C6F5)3 leads selectively to 1,4-stannabora-cyclohexa-2,5-dienes for all dialkynyltin compounds studied. In several cases, zwitterionic intermediates could be detected by multinuclear magnetic resonance spectroscopy (1H, 11B, 13C, and 119Sn NMR), and the molecular structure of such an intermediate as well as that of the final

  摘要。比较了三有机硼烷 BR3、Et-9-BBN、BPh3 和 B(C6F5)3 对各种二炔基（二有机）锡化合物的反应性（R12Sn(C≡C-R2)2，其中 R12 = –(CH2)5– , R2 = H (a), R1 = nBu, R2 = H (b), R1 = Ph, R2 = H (c), R1 = R2 = nBu (d))。1,1-碳硼化很容易在两个连续的步骤（分子间和分子内）中发生，产生锡醇或 1,4-锡硼-环六-2,5-二烯，或它们的混合物。最弱的路易斯酸性三有机硼烷 BEt3 和 Et-9-BBN 与二炔锡化合物选择性地生成锡醇，而强亲电性 B( )3 对所有研究的二炔基锡化合物选择性地生成 1,4-锡硼-环六-2,5-二烯. 在一些情况下，两性离子中间体可以通过多核磁共振波谱（1H、11B、13C 和 119Sn NMR）检测到，
• New phosphabenzenes by [4 + 2] cycloaddition of stannoles to 1-phospha-1-alkynes — determination of signs of coupling constants
  作者：Bernd Wrackmeyer、Uwe Klaus

  DOI：10.1016/0022-328x(96)06316-4

  日期：1996.8

  Stannoles bearing dialkylboryl groups in 3-position react with 1-phospha-1-alkynes P=C-(t)Bu (1) and P=C-CH(2)(t)Bu (2) by [4 + 2] cycloaddition and elimination of stannylene to give phosphabenzenes in high yield. The stannylenes oligomerise to give [R(2)(1)Sn](n) with n greater than or equal to 7 (R = Me, Et, -(CH2)(5)- or, in the case of R(1) = (t)Bu, react with the stannole itself. All phosphabenzenes are characterised by their consistent sets of NMR data. The absolute signs of the coupling constants (n)J(P-31, H-1), (n)J(P-31, C-13), (2)J(P-31, Si-29) and (2)J(Sn-119, P-31) were determined by appropriate 1D and 2D NMR experiments.