4,4'-bis((trimethylstannyl)ethynyl)biphenyl | 120120-22-1

• 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: 4,4'-bis((trimethylstannyl)ethynyl)biphenyl
• 英文别名: bis(trimethylstannylethynyl)-p-biphenyl；4,4'-bis(trimethyltin)ethynylbiphenyl；Me3SnC2(μ-4,4-C6H4-C6H4)C2SnMe3；Trimethyl-[2-[4-[4-(2-trimethylstannylethynyl)phenyl]phenyl]ethynyl]stannane
• CAS: 120120-22-1
• 化学式: C₂₂H₂₆Sn₂
• 分子量: 527.868
• InChiKey: WBHWACIRHXOOAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  trans-chloro(phenylacetylenyl)bis(triphenylphosphine)platinum 、 4,4'-bis((trimethylstannyl)ethynyl)biphenyl 在 copper(l) iodide 作用下， 以 甲苯 为溶剂， 以52%的产率得到ethynylbenzene;1-ethynyl-4-(4-ethynylphenyl)benzene;platinum(2+);triphenylphosphane
  参考文献：
  名称：

  Synthesis of highly ethynylated mono and dinuclear Pt(II) tethers bearing the 4,4′-bis(ethynyl)biphenyl (debp) unit as central core

  摘要：

  Mono and bisubstituted bis(ethynyl)biphenyl Pt(II) complexes, i.e. trans-[(R-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-p-C6H4-p-C6H4-C equivalent toC-H)], R = p-NO2C6H4 (3b), (eta (5)-C5H5)Fe(eta (5)-C5H4) (3c), and trans-[(R-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-p-C6H4-p-C6H4-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-R)], R = C6H5 (4a), p-NO2C6H4 (4b), (eta (5)-C5H5)Fe(eta (5)-C5H4) (4c), have been synthesized by the dehydrohalogenation reaction from the appropriate Pt monochloro acetylides trans-[(RC equivalent toC)Pt(PPh3)(2)Cl], R = C6H5 (1a), R =p-NO2C6H4 (1b), R = (eta (5)-C5H4)Fe(eta (5)-C5H5) (1c) and HC equivalent toC-p-C6H5-p-C6H5-C equivalent to CH, (4,4'-bis-ethynylbiphenyl), (DEBP) (2). In order to make possible a direct evaluation of the role of Pt centers on the properties of these highly ethynylated complexes, the corresponding species without Pt were prepared, i.e. C6H5-C equivalent toC-C equivalent toC-C6H4-C6H4-C equivalent toC-C equivalent toC-C6H5, (4,4'-(bis-phenylethynyl)-diethynylbiphenyl) (7), and (eta (5)-C5H5)Fe(eta (5)-C5H4)-(C equivalent toC-C equivalent toC-C6H4-C6H4-C equivalent toC-C equivalent toC)-(eta (5)-C5H4)Fe(eta (5)-C5H4)Fe(eta (5)-C5H5), (4,4 '-(bis-ferrocenylethynyl)-diethynylbiphenyl) (8). Preparation of the latter compounds was only achieved by the use of the palladium catalyzed Stille coupling reaction, since the dehydrohalogenation route afforded only homocoupled and polymeric products. The electron-donor or electron-withdrawing ligands coordinated to Pt were chosen for the purpose of tuning the optical properties of the complexes through the different charge distribution along the pi -electron conjugation. Characteristic spectroscopic features (UV-vis, FT-IR and NMR) of these complexes are discussed. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00533-7
• 作为产物：
  描述：

  4,4'-二乙炔基联苯 、 二乙胺基三甲基锡 以 neat (no solvent) 为溶剂， 以100%的产率得到4,4'-bis((trimethylstannyl)ethynyl)biphenyl
  参考文献：
  名称：

  Synthesis of highly ethynylated mono and dinuclear Pt(II) tethers bearing the 4,4′-bis(ethynyl)biphenyl (debp) unit as central core

  摘要：

  Mono and bisubstituted bis(ethynyl)biphenyl Pt(II) complexes, i.e. trans-[(R-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-p-C6H4-p-C6H4-C equivalent toC-H)], R = p-NO2C6H4 (3b), (eta (5)-C5H5)Fe(eta (5)-C5H4) (3c), and trans-[(R-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-p-C6H4-p-C6H4-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-R)], R = C6H5 (4a), p-NO2C6H4 (4b), (eta (5)-C5H5)Fe(eta (5)-C5H4) (4c), have been synthesized by the dehydrohalogenation reaction from the appropriate Pt monochloro acetylides trans-[(RC equivalent toC)Pt(PPh3)(2)Cl], R = C6H5 (1a), R =p-NO2C6H4 (1b), R = (eta (5)-C5H4)Fe(eta (5)-C5H5) (1c) and HC equivalent toC-p-C6H5-p-C6H5-C equivalent to CH, (4,4'-bis-ethynylbiphenyl), (DEBP) (2). In order to make possible a direct evaluation of the role of Pt centers on the properties of these highly ethynylated complexes, the corresponding species without Pt were prepared, i.e. C6H5-C equivalent toC-C equivalent toC-C6H4-C6H4-C equivalent toC-C equivalent toC-C6H5, (4,4'-(bis-phenylethynyl)-diethynylbiphenyl) (7), and (eta (5)-C5H5)Fe(eta (5)-C5H4)-(C equivalent toC-C equivalent toC-C6H4-C6H4-C equivalent toC-C equivalent toC)-(eta (5)-C5H4)Fe(eta (5)-C5H4)Fe(eta (5)-C5H5), (4,4 '-(bis-ferrocenylethynyl)-diethynylbiphenyl) (8). Preparation of the latter compounds was only achieved by the use of the palladium catalyzed Stille coupling reaction, since the dehydrohalogenation route afforded only homocoupled and polymeric products. The electron-donor or electron-withdrawing ligands coordinated to Pt were chosen for the purpose of tuning the optical properties of the complexes through the different charge distribution along the pi -electron conjugation. Characteristic spectroscopic features (UV-vis, FT-IR and NMR) of these complexes are discussed. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00533-7

文献信息

• New Access to Homodinuclear Half‐Sandwich Vinylidenemanganese Complexes
  作者：Koushik Venkatesan、Thomas Fox、Helmut W. Schmalle、Heinz Berke

  DOI：10.1002/ejic.200400686

  日期：2005.3

  4-C 4 H 2 S}) and R 2 PCH 2 CH 2 PR 2 (R = Me, Et) at 50 °C for 12 h to yield the corresponding dinuclear complexes in very good yields. These dinuclear tin-substituted vinylidene complexes were further treated with an excess of MeOH to give the corresponding dinuclear parent vinylidene complexes of the type [Mn(MeC 5 H 4 )(R 2 PCH 2 CH 2 PR 2 )=C=C(H)} 2 X}] (X = μ-1,4-C 6 H 4 }, R = Me, 6a; X =

  [Mn(MeC 5 H 4 )(R 2 PCH 2 CH 2 PR 2 )=C=C(SnMe 3 )} 2 X}] ( X = μ-1,4-C 6 H 4 }, R = Me, 2a; X = μ-1,4-C 6 H 4 }, R = Et, 2b; X = μ-1,3 -C 6 H 4 }, R = Me, 3a; X = μ-1,3-C 6 H 4 }, R = Et, 3b; X = μ-4,4-C 6 H 4 -C 6 H 4 }, R = Me, 4a; X = μ-4,4-C 6 H 4 -C 6 H 4 }, R = Et, 4b; X = μ-1,4-C 4 H 2 S }, R = Me, 5a; X = μ-1,4-C 4 H 2 S}, R = Et, 5b) 由[Mn(C 5 H 4 Me) (η 6 -环庚三烯)] 与 0.5 当量。相应的乙炔
• Mono‐ and Dinuclear High‐Spin Half‐Sandwich Manganese( <scp>II</scp> ) Complexes Containing Acetylide and TMEDA Ligands
  作者：Sohrab Kheradmandan、Thomas Fox、Helmut W. Schmalle、Koushik Venkatesan、Heinz Berke

  DOI：10.1002/ejic.200400006

  日期：2004.9

  half-sandwich complexes [Mn(C≡CR)(MeC5H4)(tmeda)] (R = SiMe32; Ph 3; tBu 4; C≡CSiMe35; C≡CPh 6; tmeda = N,N,N′,N′-tetramethylethylenediamine) were prepared by the reaction of [Mn(MeC5H4)2(tmeda)] (1) with 1 equiv. of the corresponding acetylene or the trimethyltin acetylide. The dinuclear complexes [Mn(C≡C−C≡CSiMe3)2(tmeda)]2 (7) and [Mn2(MeCp)2(μ1-tBuC≡C)2(μ1-tmeda)] (8), which contain Mn−Mn bonds,

  d5 高自旋 MnII 半夹心复合物 [Mn(C≡CR)(MeC5H4)(tmeda)] (R = SiMe32; Ph 3; tBu 4; C≡CSiMe35; C≡CPh 6; tmeda = N,N, N',N'-四甲基乙二胺）通过 [Mn(MeC5H4)2(tmeda)](1) 与 1 当量的反应制备。相应的乙炔或三甲基锡乙炔化物。双核配合物[Mn(C≡C-C≡CSiMe3)2(tmeda)]2(7)和[Mn2(MeCP)2(μ1-tBuC≡C)2(μ1-tmeda)](8)，其中含有Mn-Mn 键是通过分别用过量的 HC≡C-C≡CSiMe3 或 HC≡CtBu 处理 1 来合成的。[(MeC5H4)(tmeda)MnC≡C− X−C≡CMn(tmeda)(C5H4Me)] [X = 1,3- 9; 1,4- 10；4,4'-(C6H4)211] 是通过用 0.5 当量处理
• Synthesis and electronic structure of rigid rod octahedral Ru-σ-acetylide complexes
  作者：Muhammad S. Khan、Ashok K. Kakkar、Scott L. Ingham、Paul R. Raithby、Jack Lewis、Brock Spencer、Felix Wittmann、Richard H. Friend

  DOI：10.1016/0022-328x(94)80211-4

  日期：1994.6

  Ru-σ-acetylide complexes, trans-[Ru(CO)2(PnBu3)2(CC C6H5)2], trans-[ClRu(CO)2(PnBu3)2CCpC6H4C6H4 pCCRu(CO)2(PnBu3)2Cl] and trans-[Ru(CO)2(PnBu3)2CC RCC]n(R = p-C6H4, p(CH3)2C6H2) are reported. A study of the electronic structure of model metal-acetylide complexes of Group 8, M(L)2,(L′)2(RH)2, ClRu(L or L′)4RRu(L or L′)4 Cl, [M(PH3)4(RH)]2R and [M(L)(L)2(R)]n, (M  Fe, Ru; L  L′ PH3,

  单-的合成，二-和聚核钌-σ-乙炔化物，反式- [钌（CO）2（P Ñ卜3）2（CCç 6 ħ 5）2 ]，反式- [CLRU（CO）2（p ñ卜3）2 CC p C 6 ħ 4 C 6 ħ 4  p CCRu（CO）2（p ñ卜3）2 CL]和反式-[Ru（CO）2（P Ñ卜3）2 CCRCC] Ñ（R = p -C 6 H ^ 4，p CH（3）2 C ^ 6 ħ 2）的报告。组8，M（L）的模型的金属乙炔化物络合物的电子结构的研究2，（L'）2（RH）2，CLRU（L或L'）4 RRu（L或L'）4 Cl，[M（PH 3）4（RH）] 2 R和[M（L）（L）2（R）] n，（MFe，Ru; LL′PH 3，PMe 3 ; 大号CO，L'PH 3 ; řCC，CCC 6 ħ 4 CC，CHCH p C 6
• Rigid rod σ-acetylide complexes of iron, ruthenium and osmium
  作者：Zeno Atherton、Charlotte W. Faulkner、Scott L. Ingham、Ashok K. Kakkar、Muhammad S. Khan、Jack Lewis、Nicholas J. Long、Paul R. Raithby

  DOI：10.1016/0022-328x(93)83367-5

  日期：1993.12

  [M(DEPE)2CCRCC]n (M  Fe2+, Ru2+), [Os(DPPM)2CCRCC-]n (R = p-C6H4- C6H4-p, p-C6H4, p-C6H2(CH3)2) complexes is demonstrated. The linear arrangement of the acetylenic units around octahedral metal centres is confirmed by a single crystal X-ray structure determination of the model complex trans-[Ru(DPPE) 2(CCC6H5)2].

  双（三甲基锡烷基）炔基中的第8族金属的制备合成的实用程序（铁2+，钌2+，锇2+）σ -乙炔化单体，M（DEPE）2（CCC 6 ħ 5）2（M的Fe 2+，钌2+ ; DEPE = 1,2-双（二乙基膦基）乙烷），钌（DPPE）2（CCC 6 ħ 5）2（DPPE = 1,2-双（二苯基膦基）乙烷），锇（DPPM）2（CCC 6 ħ 5）2（DPPM = 1,2-双（二苯基膦基）甲烷）和聚合物，[M（DEPE）2]CCRCC Ñ（M的Fe 2+，钌2+），[Os（DPPM）2 CCRCC-] Ñ（R = p - ç 6 ħ 4 - Visual C 6 H ^ 4 - p，p -C 6 H ^ 4，p -C 6 H ^ 2（CH 3）2）配合物是证明。乙炔单元在八面体金属中心周围的线性排列通过模型络合物反式-[Ru（DPPE）2的单晶X射线结构确定得到确认（CCC
• Synthesis of monomeric and oligomeric bis(acetylide) complexes of platinum and rhodium
  作者：Simon J. Davies、Brian F. G. Johnson、Muhammad S. Khan、Jack Lewis

  DOI：10.1039/c39910000187

  日期：——

  Treatment of the complexes trans-[M(PBu3)2Cl2](M = Ni, Pd or Pt) with one equivalent of the reagent Me3SnCC–R–CCSnMe3(R =p-C6H4) affords the polymeric species trans-[–M(PBu3)2-CC–R–CC–]n, where as if two equivalents of the tin reagent are used in this reaction, when M = Pt, the complex trans-[Me3SnCC–R–CC–Pt(PBu3)2-CC–R–CCSnMe3] may be isolated, a precursor for further syntheses; the complex mer-trans-[Rh(PMe3)3(SnMe3)(CCPh)2] has been prepared by the addition of Me3SnCCPh to [Rh(PMe3)4][Cl], and this latter species, when treated with Me3SnCC–R′–CCSnMe3(R′=p-C6H4–C6H4–p), affords the oligomeric compound mer-trans-[–Rh(PMe3)3(SnMe3)–CC–R′–CC–]n.

  用一个当量的试剂 Me3SnCC-R-CCSnMe3（R =p-C6H4）处理反式-[M(PBu3)2Cl2]（M = Ni、Pd 或 Pt）络合物，可得到反式-[-M(PBu3)2-CC-R-CC-]n 聚合物、其中，如果在该反应中使用两个当量的锡试剂，当 M = Pt 时，可以分离出反式-[Me3SnCC-R-CC-Pt(PBu3)2-CC-R-CCSnMe3]复合物，它是进一步合成的前体；通过在[Rh(PMe3)4][Cl]中加入 Me3SnCCPh，制备出复合物 mer-trans-[Rh(PMe3)3(SnMe3)(CCPh)2]，后一种复合物、用 Me3SnCC-R′-CCSnMe3(R′=p- - -p)处理后，得到低聚化合物 mer-trans-[-Rh(PMe3)3(SnMe3)-CC-R′-CC-]n。