1,3-dibromo-5-(ferrocenylethynyl)benzene | 189580-49-2

• 英文名称: 1,3-dibromo-5-(ferrocenylethynyl)benzene
• 英文别名: 1-(η5-cyclopentadienyl)Fe(η5-C5H4CC)-3,5-Br2C6H3；[1,3-dibromo-5-(ferrocenyl)ethynylbenzene]；1-(FcCC)-3,5-Br2-C6H3；[1,3-Br2-5-FcCC-C6H3]；1-(FcCC)-3,5-Br2C6H3
• CAS: 189580-49-2
• 化学式: C₁₈H₁₂Br₂Fe
• 分子量: 443.948
• InChiKey: LPHDQOJHUJBCRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
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• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-5-(ferrocenylethynyl)benzene 、 碘 在 n-BuLi 、 sodium thiosulfate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到[1-iodo-3-bromo-5-(ferrocenyl)ethynylbenzene]
  参考文献：
  名称：

  基于1,3,5-三乙炔基苯连接单元的过渡金属配合物

  摘要：

  报道了一系列独特的杂多核过渡金属化合物的合成。配合物1‐I‐3‐Br‐5‐（FcC≡C）‐C 6 H 3（4），1‐Br‐3‐3（bpy‐C≡C）‐5‐（FcC≡C）‐C 6 H 3（6），1,3-（BPY-C≡C）2 -5-（FcC≡C）-C 6 H ^ 3（7），1-（X C≡C）-3-（BPY-C≡ C）‐5‐（FcC≡C）‐C 6 H 3（8，X = SiMe 3 ; 9，X = H），1‐（HC≡C）‐3 ‐ [（CO）3 ClRe（bpy‐C [C）]-5-（FcCC）-6 H 3（11），1 [[（Ph 3 P）AuC≡C] -3 [[CO）3 ClRe（bpy-C≡C）]-5-（FcC≡C）-C 6 H 3（13）， 1 - [（PH 3 P）AuC≡C] -3-（BPY-C≡C）-5-（FcC≡C）-C 6 H ^ 3（14），[1 - [（PH 3 PAuC≡C] -3

  DOI：

  10.1002/zaac.201000243
• 作为产物：
  描述：

  二茂铁乙炔 、 1,3-二溴-5-碘苯 在 (PPh₃)2PdCl₂ 、 CuI 作用下， 以 not given 为溶剂， 生成 1,3-dibromo-5-(ferrocenylethynyl)benzene
  参考文献：
  名称：

  基于1,3,5-三乙炔基苯连接单元的过渡金属配合物

  摘要：

  报道了一系列独特的杂多核过渡金属化合物的合成。配合物1‐I‐3‐Br‐5‐（FcC≡C）‐C 6 H 3（4），1‐Br‐3‐3（bpy‐C≡C）‐5‐（FcC≡C）‐C 6 H 3（6），1,3-（BPY-C≡C）2 -5-（FcC≡C）-C 6 H ^ 3（7），1-（X C≡C）-3-（BPY-C≡ C）‐5‐（FcC≡C）‐C 6 H 3（8，X = SiMe 3 ; 9，X = H），1‐（HC≡C）‐3 ‐ [（CO）3 ClRe（bpy‐C [C）]-5-（FcCC）-6 H 3（11），1 [[（Ph 3 P）AuC≡C] -3 [[CO）3 ClRe（bpy-C≡C）]-5-（FcC≡C）-C 6 H 3（13）， 1 - [（PH 3 P）AuC≡C] -3-（BPY-C≡C）-5-（FcC≡C）-C 6 H ^ 3（14），[1 - [（PH 3 PAuC≡C] -3

  DOI：

  10.1002/zaac.201000243

文献信息

• Heterotrimetallic M−M′−M′′ Transition Metal Complexes Based on 1,3,5-Triethynylbenzene: Synthesis, Solid State Structure, and Electrochemical and UV−Vis Characterization. EPR Analysis of the <i>in Situ</i> Generated Associated Radical Cations
  作者：Rico Packheiser、Petra Ecorchard、Tobias Rüffer、Manja Lohan、Björn Bräuer、Frédéric Justaud、Claude Lapinte、Heinrich Lang

  DOI：10.1021/om800206k

  日期：2008.7.1

  The synthesis of a series of complexes with different organometallic building blocks unsymmetrically arranged around the periphery of a 1,3,5-triethynylbenzene core is discussed. They are accessible by diverse consecutive reaction sequences, which allow the introduction of transition metal units such as Fc, [((t)Bu(2)bpy)(CO)(3)Re], [(eta(5)-C5H5)(Ph3P)(2)Ru], [(eta(5)-C5H5)(Ph3P)(2)Os], and trans-[(Ph3P)(2)(Cl)Pt] (Fc = (eta(5)-C5H5)(eta(5)-C5H4)Fe; (t)Bu(2)bpy = 4,4 '-di-tert-butyl-2,2 '-bipyridyl). The solid state structures of five complexes have been determined. The electrochemical behavior of the newly synthesized mono-, heterobi-, and heterotrimetallic assemblies have been studied, showing that there is no significant electronic interaction between the respective metal atoms. UV-vis spectroscopic measurements suggest a weak interaction between the appropriate metal atoms. The associated radical cations were in situ generated by stepwise chemical oxidation and characterized by continuous wave electron paramagnetic resonance (EPR) investigations in X-band performed at low temperatures.
• Ethynylferrocene Compounds of 1,3,5-Tribromobenzene
  作者：Herbert Fink、Nicholas J. Long、Angela J. Martin、Giuliana Opromolla、Andrew J. P. White、David J. Williams、Piero Zanello

  DOI：10.1021/om9701027

  日期：1997.6.1

  The new compounds 1,3-dibromo-5-(ferrocenylethynyl)benzene (1), 1-bromo-3,5-bis(ferrocenylethynyl)benzene (2), and 1,3,5-tris(ferrocenylethynyl)benzene (3) have been synthesized by palladium-catalyzed cross-coupling reactions and characterized, and the crystal structures of 1 and 3 have been determined; electrochemical studies show chemically reversible oxidations with single-step one-electron, two-electron, and three-electron processes per molecule, respectively, indicating that in 2 and 3 the iron(II) centers do not electronically communicate with each other.
• Mixed transition–metal complexes based on multitopic 1,3,5-triethynyl- and 1-diphenylphosphino-3,5-diethynyl-benzene linking units
  作者：Rico Packheiser、Heinrich Lang

  DOI：10.1016/j.ica.2010.10.029

  日期：2011.1

  The synthesis and reaction chemistry of heteromultimetallic transition metal complexes in which Fc, [(eta(6)-C6H5)Cr(CO)(3)], [(Ar3P)Au], [AuC C-bpy] and [[Ti](mu-sigma,pi-C CSiMe3)(2)}Cu](+) units (Fc = (eta(5)-C5H4)(eta(5)-C5H5)Fe; [Ti] = (eta(5)-C5H4SiMe3)(2)Ti; bpy = 2,2'-bipyridyl-5-yl) are linked by alkynyl-, benzene-and phosphane- or bipyridyl-based connecting moieties is discussed. In context with this background the preparation of neutral heterotrimetallic 1-(FcC C)-3-[(CO)(3)Cr(eta(6)-C6H5C C)]-5-[(Ph3P)AuC C]C6H3 (10) and ionic heteropentametallic [1-(FcC C)-3-[(CO)(3)Cr(eta(6)-C6H5C C)]-5-[(PPh2)AuC C-bpy([Ti](mu-sigma,pi-C CSiMe3)(2)}Cu)]C6H3](PF6) (19) from 1-iodo-3,5-dibromobenzene (1) is reported by applying consecutive reaction methodologies including substitution, complexation and carbon-carbon cross-coupling reactions.The identities of all complexes have been confirmed by elemental analysis and IR, H-1 and P-31H-1} NMR spectroscopy; heteropentametallic 19 was additionally characterized by ESI-TOF mass-spectrometry. (C) 2010 Elsevier B.V. All rights reserved.