1,4-bis(trimethylstannyl)-1,3-butadiyne | 40762-69-4

• 分子结构分类: 有机化合物 - 乙炔化物 - 金属乙炔化物
• 英文名称: 1,4-bis(trimethylstannyl)-1,3-butadiyne
• 英文别名: 1,4-bis(trimethylstannyl)buta-1,3-diyne；bis(trimethylstannyl)diacetylene；bis(trimethylstannyl)butadiyne；Me3SnC*CC*CSnMe3；Me₃Sn(C₄)SnMe₃；1,4-Bis--butadiin-(1,3)；Stannane, 1,3-butadiyne-1,4-diylbis[trimethyl-；trimethyl(4-trimethylstannylbuta-1,3-diynyl)stannane
• CAS: 40762-69-4
• 化学式: C₁₀H₁₈Sn₂
• 分子量: 375.673
• InChiKey: XURYVRLKLHXRGI-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  258.1±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  七氟-2-碘代丙烷 、 1,4-bis(trimethylstannyl)-1,3-butadiyne 在 azobisisobutyronitrile 作用下， 以30%的产率得到Trimethyltin heptafluorisopropyldiacetylene
  参考文献：
  名称：

  Klyuchinskii, S. A.; Demchenko, L. V.; Zavgorodnii, V. S., Journal of general chemistry of the USSR, 1988, vol. 58, p. 208 - 209

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-1-methoxybut-1-en-3-yne 、 三甲基氯化锡 在 Li(C₄H₉) 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到1,4-bis(trimethylstannyl)-1,3-butadiyne
  参考文献：
  名称：

  通过钯催化的碳-金属键形成合成金属乙炔

  摘要：

  The iron complex CpFe(CO)2I (1) undergoes a clean coupling reaction of the Fe-I bond with the Sn-C= bond of various trialkyltin acetylides 3SnC=CR' (R' = H, Pr, Bu, Ph) in the presence of a catalytic amount (5%) of (CH3CN)2PdCl2 to give the corresponding sigma-alkynyl metal complexes CpFe(CO)2C=CR' [R' = H (2), Pr (3), Bu (4), Ph (5)] in 60-70% yields. Under the same conditions, 1 equiv of complex 1, CpFe(CO)2I, in the presence of palladium, reacts with the 1-(trimethylstannyl)-1,3-butadiyne (CH3)3SnC=CC=CH (8) to form the iron complex CP(CO)2FeC=CC=CH (11) and 2 equiv reacts with 1,4-bis(trimethyl-stannyl)-1,3-butadiyne, (CH3)3SnC=CC=CSn(CH3)3 (10), to yield the bimetallic complex Cp-(CO)2FeC=CC=CFe(CO)2Cp (12) possessing the eta2(sigma,sigma)-1,3-butadiyne-1,4-diyl ligand bridging the two iron atoms.

  DOI：

  10.1021/om00060a056

文献信息

• Dinuclear and Mononuclear Chromium Acetylide Complexes
  作者：Carolina Egler‐Lucas、Olivier Blacque、Koushik Venkatesan、Alberto López‐Hernández、Heinz Berke

  DOI：10.1002/ejic.201100929

  日期：2012.3

  (10), respectively. The complexes 2, 2[SnMe3Cl2]2, 2[PF6]2, 3[SnMe3Cl2]2, 3[BPh4]2, and 6–10 displayed paramagnetic behavior. Electrochemical studies performed on the dinuclear complexes (2), (2[SnMe3Cl2]2), (3[SnMe3Cl2]2), and (5) showed one two-electron redox wave revealing a class-I type behavior based on the Robin–Day classification, which is untypical for dinuclear complexes bridged by a butadiyne

  反式-Cl2Cr(dmpe)2 (1) [dmpe = 1,2-双（二甲基膦基）乙烷] 与 0.5 当量的反应。Me3Sn–C≡C–C≡C–SnMe3 或 Me3Sn–C≡C–C6H4–C≡C–SnMe3 得到双核配合物 trans-[Cl(dmpe)2Cr≡C–C≡C–C≡Cr(dmpe )2Cl] (2)、反式-[Cl(dmpe)2Cr–C≡C–C≡C–Cr(dmpe)2Cl][SnMe3Cl2]2 (2[SnMe3Cl2]2) 和反式-[Cl(dmpe) 2Cr–C≡C–C6H4–C≡C–Cr(dmpe)2Cl][SnMe3Cl2]2 (3[SnMe3Cl2]2)，可以转化为 2[PF6]2 和 3[BPh4]2 盐。进行2中的氯基团的取代以获得相应的碘(4)和(三甲基甲硅烷基)炔基(5)配合物。仅使用 1 当量即可使用类似的反应和处理。相应的炔基配体 [Me3Sn–C≡C–R (R
• Di-, tri-, pseudo-di- and pseudo-tetra-acetylenic polymers of platinum: Synthesis, characterization and optical spectra
  作者：Jack Lewis、Muhammad S. Khan、Ashok K. Kakkar、Brian F.G. Johnson、Todd B. Marder、Helen B. Fyfe、Felix Wittmann、Richard H. Friend、Ann E. Dray

  DOI：10.1016/0022-328x(92)80033-t

  日期：1992.2

  Reactions of Me3Sn-CC-(CC-)m-CC-SnMe3 (m= 0, 1) (1, 2), Me3Sn-(CC)m-p-C6H4-(CC)m-SnMe3 (m = 1, 2) (3, 4) with the platinum metal halide complexes, [Pt(XnBu3)2Cl2] (where X = P (5), As (6)) afford high molecular weight polymeric species, [-Pt(XnBu3)2-CC-(CC)m-CC-]n (7-10), and [-Pt(PnBu3)2-(CC)m-p-C6H4-(CC)m-]n (11, 12) in excellent yields. Investigations of the optical absorption and photoluminescence

  的反应我3的Sn-CC-（CC-）米-CC-SnMe 3（米= 0，1）（1，2）中，Me 3 Sn的（CC）米- p - ç 6 ħ 4 - （CC）米-SnMe 3（米= 1，2）（3，4与铂金属卤化物复合物），[PT（X ñ卜3）2氯2 ]（其中X = P （5），As（6））提供高分子量的聚合物，[-Pt（X nBu 3）2- CC-（CC）m- CC-] n（7-10）和[-Pt（P n Bu 3）2-（CC）m - p -C 6 H 4-（CC）m- ] n（11，12）的良率。这些配合物的光吸收和光致发光光谱的研究表明，通过链上金属位点扩展了π电子共轭，三乙炔的π-π*能隙比二乙炔聚合物的配合物低。在吸收和发射方面都观察到与-CC-拉伸频率相关的良好解析的振动子结构，表明二乙炔和三乙炔聚合物具有很强的电子-声子耦合。
• Electronic Communication in C4-Bridged Binuclear Complexes with Paramagnetic Bisphosphane Manganese End Groups
  作者：Sohrab Kheradmandan、Katja Heinze、Helmut W. Schmalle、Heinz Berke

  DOI：10.1002/(sici)1521-3773(19990802)38:15<2270::aid-anie2270>3.0.co;2-6

  日期：1999.8.2

  Building blocks for conducting polymers or NLO materials are the linear, unsaturated carbon chain bridged manganese complexes 1(n+) (n=0-2). All oxidation states were investigated spectroscopically and by X-ray structure determinations. The analytical data confirm a communication of the electrons over the C(4) chain-a prerequisite for electrical conductivity and NLO properties of oligo- or polymeric materials.
• Stepwise Construction of an Iron-Substituted Rigid-Rod Molecular Wire: Targeting a Tetraferra–Tetracosa–Decayne
  作者：Franziska Lissel、Thomas Fox、Olivier Blacque、Walther Polit、Rainer F. Winter、Koushik Venkatesan、Heinz Berke

  DOI：10.1021/ja400078c

  日期：2013.3.13

  trans-Fe(depe)(2)I-2 (depe =1,2-bis(diethylphosphino)ethane) was employed to stepwise incorporate Fe(II) centers into a rigid-rod butadiyne based 5,10,15,20-tetraferratetracosa-1,3,6,8,11,13,16,18,21,23-decayne. The iterative synthesis first connects two Fe(II) centers via a central butadiynediyl ligand to provide I-Fe(depe)(2)-C-4-Fe(depe)(2)-I (2), then extends the system by substituting the terminal halides of 2 to yield Me3SiC4-Fe(depe)(2)-C-4-Fe(depe)(2)-C4SiMe3 (3). Further modification of the termini gives the deprotected and stannylated compounds RC4-Fe(depe)(2)-C-4-Fe(depe)(2)-C4R (4 and 5; R = H, Sn(CH3)(3), respectively). Transmetalation with two more mononuclear units furnishes the homometallic tetranuclear compound I-Fe(depe)(2)-C-4-Fe(depe)(2)-C-4-Fe(depe)(2)-C-4-Fe(depe)(2)-I (6), to which two more butadiynyl units were attached to give Me3SiC4-Fe(depe)(2)-C-4-Fe(depe)(2)-C-4-Fe(depe)(2)-C-4-Fe(depe)(2)-C4SiMe3 (7). All compounds were characterized by NMR, IR, and Raman spectroscopies and by elemental analyses. X-ray diffraction studies were carried out on the dinuclear complexes revealing highly symmetrical rigid-rod structures. Cyclic voltammetric studies showed that compounds 2-7 undergo reversible and well-defined oxidations with high K-c values indicating thermodynamically stable mixed valence species. While the number of the oxidation waves of compounds 2, 6, and 7 are equivalent to the number of metal centers, the dinuclear complexes 3, 4, and 5 exhibit three reversible oxidation waves, one at significantly more positive potential. Two redox waves were attributed to the oxidation of the metal centers, while the remaining one is due to the oxidation of the butadiynediyl ligand. The electronic properties of complexes 2, 3, and 7 were investigated by spectroelectrochemical measurements.
• Synthetic Access to Half-Sandwich Manganese C₄ Cumulenic Complexes
  作者：Koushik Venkatesan、Olivier Blacque、Thomas Fox、Montserrat Alfonso、Helmut W. Schmalle、Heinz Berke

  DOI：10.1021/om049551e

  日期：2004.9.1

  The vinylalkynyl complexes Mn(C5H4R')(R"2PCH2CH2PR"(2))(=C CSnPh3C=-CSnPh3) (5, 6) were obtained in good yields by treatment of Mn(C5H4R')(eta(6)-cycloheptatriene) (R' = H (1a), Me (1b)) with 1 equiv of Ph(3)SnCdropCCdropCSnPh(3) and R"2PCH2CH2PR"(2) (R" = CH3 (dmpe), C2H5 (depe)). The theoretically characterized (DFT) C-4 cumulenic species Mn(C5H4R')(R"2PCH2CH2PR"(2))=C=C=C C(SnPh3)(2)} (7, 8) were obtained by photolysis of the tin-substituted vinylalkynyl complexes 5 and 6. Subsequently 7 and 8 could be converted into the parent cumulenic species Mn(C5H4R')(R"2PCH2CH2PR"(2))=C=C=C=C(H)(2)} (9, 10) by reacting complexes 7 and 8 with TBAF (5% H2O) at -40 degreesC. The difference in the thermodynamic stabilities between the complexes 7 and 8 and complexes 9 and 10 was traced by DFT calculations using Mn(C5H5)(dHpe)=C=C=C=C(SnMe3)(2)} (4-H) and Mn(C5H5)(dHpe)=C=C=C=CH2} (9-H) as model complexes. Treatment of the vinylalkynyl complex with an excess of MeOH led to the formation of a dinuclear complex with a C-8 chain between two manganese centers. The cumulenic complexes and the vinylalkynyl complexes were characterized by NMR and vibrational spectroscopy and elemental analyses. An X-ray diffraction study has been performed on complex 4b.