1'-(tri-n-butylstannyl)-1-ferrocenecarboxaldehyde | 124944-43-0

• 英文名称: 1'-(tri-n-butylstannyl)-1-ferrocenecarboxaldehyde
• 英文别名: 1'-(tri-n-butylstannyl)ferrocene-1-carboxaldehyde；[Fe(η5-C5H4-CHO)(η5-C5H4Sn(nBu)3)]
• CAS: 124944-43-0
• 化学式: C₂₃H₃₆FeOSn
• 分子量: 503.095
• InChiKey: DMEYSKNUFKAGSY-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：
  None
• 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'-(tri-n-butylstannyl)-1-ferrocenecarboxaldehyde 在 碘 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到1'-iodoferrocenecarboxaldehyde
  参考文献：
  名称：

  没有内置螯合基团的甲酰胺和炔烃的对映选择性双CH环。

  摘要：

  在没有内置螯合基团的情况下，可轻松获得的甲酰胺和炔烃实现了两次CH环化。事实证明，由庞大的BINOL衍生的手性仲氧化膦（SPO）配体实现的Ni-Al双金属催化对于高反应性和高选择性至关重要。该反应使用现成的甲酰胺作为起始原料，并为40-98％的收率和93-99％ee的广泛的手性二茂铁提供了一条简明的合成途径。

  DOI：

  10.1002/anie.202001267
• 作为产物：
  描述：

  1,1'-bis(tri-n-butylstannyl)ferrocene 、 N,N-二甲基甲酰胺 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到1'-(tri-n-butylstannyl)-1-ferrocenecarboxaldehyde
  参考文献：
  名称：

  1,1'-双（三正丁基锡烷基）二茂铁：选择性重金属化反应用于合成新的二茂铁配体

  摘要：

  DOI：

  10.1021/om00117a049

文献信息

• Synthesis and characterization of water-soluble ferrocene-dendrimers
  作者：Edwin R. de Jong、Eric Manoury、Jean-Claude Daran、Cédric-Olivier Turrin、Jérôme Chiffre、Alix Sournia-Saquet、Wolfgang Knoll、Jean-Pierre Majoral、Anne-Marie Caminade

  DOI：10.1016/j.jorganchem.2012.07.048

  日期：2012.11

  The synthesis of two new families of water-soluble phosphorus dendrimers of type Poly(PhosphorHydrazone) (PPH) incorporating ferrocene(s) in their internal structure is reported. In the first series, the ferrocene is located at the core and the dendrimers (first and second generations) are ended either by ammonium groups or carboxylate groups, both ensuring the solubility in water. The electrochemical

  据报道，合成了两个新的聚磷（Hydrazone）型（PPH）型水溶性磷树枝状聚合物，其内部结构中包含二茂铁。在第一个系列中，二茂铁位于核心，树枝状大分子（第一代和第二代）的末端是铵基或羧酸酯基，均确保了其在水中的溶解度。报告了其中之一的电化学性质。合成了适合用作树枝状大分子的分支的新的双官能二茂铁，并通过X射线衍射对其进行了表征。它已被用于合成第二系列的树枝状大分子，该树枝状大分子包含24个二茂铁，位于第二代水平的分支中。
• 1,1′-Disubstituted Ferrocenyl Carbohydrate Chloroquine Conjugates as Potential Antimalarials
  作者：Christoph Herrmann、Paloma F. Salas、Jacqueline F. Cawthray、Carmen de Kock、Brian O. Patrick、Peter J. Smith、Michael J. Adam、Chris Orvig

  DOI：10.1021/om300354x

  日期：2012.8.27

  This work presents a new class of organometallic antimalarials, based on a ferrocene scaffold, bearing a chloroquine derivative and a 1,2;3,5-(diisopropylidene)-alpha-D-glucofuranose moiety in a 1,1'-heteroannular substitution pattern. Synthesis proceeds via orthogonal functionalization of ferrocene, giving 1-acetoxy-1'-(1,3-dioxan-2-yl)ferrocene (15) as the precursor for modular introduction of the carbohydrate (16, 17) followed by subsequent reductive amination with chloroquine building blocks 8-10, yielding the 1-[3-(7-chloroquinolin-4-ylamino)alkylamino]-1'-[6-(1,2;3,5-diisopropylidene)-alpha-D-glucofuranosidyl]ferrocenes 18-20. After complete characterization of these new, trifunctional conjugates, they were examined for their antiplasmodial activity in a chloroquine-susceptible strain of Plasmodium falciparum (D10) and in two chloroquine-resistant strains (Dd2 and K1). Their activity was compared to that of the monosubstituted reference conjugates 1-3 and the 1,2-disubstituted regioisomers 4-6. Compounds 19 and 20 exhibited consistently high activity in in vitro antiplasmodial activity assays performed in Dd2 and K1 strains, performing better than the reference compounds chloroquine and the monosubstituted and 1,2-disubstituted compounds 1-6.
• Cellulose-Based Polymers with Long-Chain Pendant Ferrocene Derivatives as Organometallic Chromophores
  作者：Fan Zhang、Volkmar Vill、Jürgen Heck

  DOI：10.1021/om0343216

  日期：2004.8.1

  Selective transmetalation reactions via 1,1'-distannylated ferrocene enables the synthesis of the new ferrocenyl chromophore [Fe(eta(5)-C5H4-CH2OH)(eta(5)-C5H4-CH=CH-C7H7)] (6). Coupling reactions of complex 6 with corresponding alkyl halides reveal the sandwich compounds [Fe(eta(5)-C5H4-CH2OCH3)(eta(5)-C5H4-CH=CH-C7H7)] (7), [Feeta(5)-C5H4-CH2O(CH2)(6)Br}(eta(5)-C5H4-CH=CH-C7H7)] (8), [Feeta(5)-C5H4-CH2O(CH2)(6)OTHP}(eta(5)-C5H4-CH=CH-C7H7)] (9) (THP = tetrahydropyranyl), and [Feeta(5)-C5H4-CH2O(CH2)(6)I}(eta(5)-C5H4-CH=CH-C7H7)] (10), which are potential precursors for dipolar donor-acceptor complexes, providing nonlinear optical properties. The synthesis of the THP derivative 9 was intended as a precursor for the hydroxy-terminated compound [Feeta(5)-C5H4-CH2O(CH2)(6)OH}(eta(5)-C5H4-CH=CH-C7H7)] (11), which would be a suitable starting material for a coupling reaction with modified cellulose. However, an acid-catalyzed cleavage of the THP group of 9 in ethanol solution resulted in the formation of [Fe(eta(5)-C5H4-CH2OCH2CH3)(eta(5)-C5H4-CH=CH-C7H7)] (12) instead of 11. The fixation of ferrocenyl chromophores to 2,3-di-O-methyl cellulose was successful by using the ferrocenyl derivative 10, which reveals 2,3-di-O-methyl-6-O-partially[Feeta(5)-C5H4-CH2O(CH2)(6)}(eta(5)-C5H4-CH=CH-C7H7)] cellulose (18) with different DS [0.1 (18a), 0.2 (18b), 0.3 (18c), 0.5 (18d), 0.6(18e)], depending on the reaction conditions. 1.8a-e were characterized by H-1 NMR, H-1-C-13 correlation spectroscopy, UV/vis spectra, and cyclic voltammetry (18c). Polarization microscopy observations of the cellulose derivative 18c demonstrate its thermotropic and lyotropic liquid crystallinities. Reaction of 12 with [Cp*Ru(CH3CN)(3)]PF6 forms the dipolar monohydro sesquifulvalene complex [Fe(eta(5)-C5H4-CH2OC2H5)eta(5) -C5H4-CH= CH-(eta(6)-C7H7)}RuCp*]PF6 (13), indicating that the ferrocenyl derivatives 7-10 can in principle be transformed to dinuclear, dipolar, monocationic, monohydro sesquifulvalene complexes and opens the feasibility of introducing dinuclear and dipolar sesquifulvalene units as pendant units of a cellulose backbone, which have potential nonlinear optical properties.
• Selective functionalization of the 1′-position in ferrocenecarbaldehyde
  作者：Gabriel Iftime、Caroline Moreau-Bossuet、Eric Manoury、Gilbert G. A. Balavoine

  DOI：10.1039/cc9960000527

  日期：——

  An efficient and selective new method for the preparation of unsymmetrical 1,1'-disubstituted ferrocenes by a one-pot procedure, starting from ferrocenecarbaldehyde, is disclosed.
• WRIGHT, MICHAEL E., ORGANOMETALLICS, 9,(1990) N, C. 853-856
  作者：WRIGHT, MICHAEL E.

  DOI：——

  日期：——