1-ferrocenyl-3-thiabutan-1-one | 360774-25-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-ferrocenyl-3-thiabutan-1-one
• 英文别名: cyclopenta-1,3-diene;1-cyclopenta-1,3-dien-1-yl-2-methylsulfanylethanone;iron(2+)
• CAS: 360774-25-0
• 化学式: C₁₃H₁₄FeOS
• 分子量: 274.167
• InChiKey: YRMKGEPIZFFWLJ-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-ferrocenyl-3-thiabutan-1-one 在 硼烷二甲硫醚络合物 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以88%的产率得到(2-(methylthio)ethyl)ferrocene
  参考文献：
  名称：

  Newly Synthesized Heteronuclear Ruthenium(II)/Ferrocene Complexes Suppress the Growth of Mammary Carcinoma in 4T1-Treated BALB/c Mice by Promoting Activation of Antitumor Immunity

  摘要：

  The two new heterometallic Ru(II)-tpy/ferrocene complexes [Ru(tpy)Cl-2(mtefc)] (1) and [Ru(tpy)-Cl-2(mtpfc)] (2) (where tpy = 2,2':6',2"-terpyridine, mtefc = (2-(methylthio)ethyl)ferrocene, and mtpfc = (3-(methylthio)propyl)ferrocene) have been synthesized and then characterized through elemental analysis, followed by various spectroscopic (IR, UV-vis, 1D and 2D NMR) and mass spectrometric techniques (MALDI TOF and ESI Q-TOF MS). UV-vis and fluorescence spectroscopy and viscometry were employed to study the interactions of the complexes 1 and 2 with calf thymus DNA. Both 1 and 2 expelled ethidium bromide (EB) from the EB/DNA complex (K-sv = (1.5-1.8) X 10(4) M-1), which suggested that the complexes intercalated into the double helix of DNA. Both complexes strongly quenched the fluorescence of tryptophan residues in serum albumin through both static and dynamic quenching. Molecular docking confirmed the intercalative mode of complex interaction with DNA. The docking results implied that 1 and 2 interacted with hydrophobic residues of albumin, particularly with those lying in the proximity of Tyr 160. We here demonstrate the high cytotoxic potential of complexes 1 and 2 against the breast cancer cells that originated either from humans (MDA-MB-231) or from mice (4T1), with apoptosis being the main mechanism of complex-induced cell death. It is worth noting that both complexes promoted activation of innate and acquired antitumor immunity, which contributed to the reduced growth and progression of mammary carcinoma in vivo.

  DOI：

  10.1021/acs.organomet.8b00604
• 作为产物：
  描述：

  二茂铁 、 (甲硫基)乙酸 在 三氯化磷 、 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 1-ferrocenyl-3-thiabutan-1-one
  参考文献：
  名称：

  二甲基（2-氧代-2-二茂铁基乙基）ulf碘化物-在合成含二茂铁的环丙烷中有用的二茂铁基卡宾的合成等价物

  摘要：

  室温下1-二茂铁基-3-硫代丁-1-酮与甲基碘在乙腈中的反应生成二甲基（2-氧代-2-二茂铁基乙基）碘化ulf，其特征在于有光谱数据（1 H NMR，13 C NMR ，IR）和X射线晶体学分析。该盐与碱（氢化钠）在乙腈中反应，生成稳定的内酯-二甲基s铁茂铁酰甲基化物，然后使其与七个共轭烯酮进行反应。获得的结果表明，该方法可能是一种新的有用的方法，用于含二茂铁的环丙烷。

  DOI：

  10.1016/j.tetlet.2012.08.102

文献信息

• The palladium(<scp>ii</scp>) complex of N,N-diethyl-1-ferrocenyl-3-thiabutanamine: synthesis, solution and solid state structure and catalytic activity in Suzuki–Miyaura reaction
  作者：Ivan Damljanović、Dragana Stevanović、Anka Pejović、Danijela Ilić、Marija Živković、Jovana Jovanović、Mirjana Vukićević、Goran A. Bogdanović、Niko S. Radulović、Rastko D. Vukićević

  DOI：10.1039/c4ra08140d

  日期：——

  first results on the synthesis of N,N-diethyl-1-ferrocenyl-3-thiabutanamine, its coordination with palladium(II), the complete characterization of the thus obtained complex (including single crystal X-ray analysis for the complex in two polymorphic forms) and screening of its catalytic activity in Suzuki–Miyaura coupling of phenylboronic acid with several aryl bromides. The complex, either purified and

  在本文中，我们希望提供有关N，N-二乙基-1-二茂铁基-3-硫代丁胺的合成，其与钯（II）的配位，由此获得的配合物（包括单晶X-射线分析复合物的两种多晶型形式），并筛选其在苯硼酸与几种芳基溴化物的Suzuki-Miyaura偶联反应中的催化活性。络合物，先纯化后再添加到反应混合物中，或就地生成，被证明是铃木-宫浦coupling合中极好的前催化剂。溶液中配合物的化学行为通过详细的NMR分析和循环伏安法测量进行评估，这使我们能够得出许多机理结论。
• Sulfur‐Containing Ferrocenyl Alcohols and Oximes: New Promising Antistaphylococcal Agents
  作者：Danijela Ilić、Ivan Damljanović、Dragana Stevanović、Mirjana Vukićević、Polina Blagojević、Niko Radulović、Rastko D. Vukićević

  DOI：10.1002/cbdv.201200029

  日期：2012.10

  values were either under the 10 μg/ml MIC limit recognized to delimit efficient antimicrobials or were comparable to/lower than those of the used positive controls (tetracycline/nystatin). The most susceptible organism was found to be Staphylococcus aureus with MIC values even reaching 0.001 μg/ml. The presence of -CH(OH)(CH(2))(n)S- and -CH(=NOH)(CH(2))(n)S- (n=1 or 2) structural fragments seems to be essential

  一个小型图书馆，包含四个不同系列的新二茂铁衍生物，2-（烷基硫烷基）-1-二茂铁基乙烷-1-醇，3-（烷基硫烷基）-1-二茂铁基丙烷-1-醇，（E）-和（Z）-2 -（烷基硫烷基）-1-二茂铁基乙烷-1-酮肟，和（E）-和（Z）-3-（烷基硫烷基）-1-二茂铁基丙烷-1-酮肟（总共36种化合物）从二茂铁开始合成和相应的硫烷基酸。对所有化合物进行光谱分析（IR和NMR）并进行电化学表征。通常，发现所获得的化合物对被测微生物（六种常见人类病原体）表现出非常强的抗菌活性（肉汤微稀释法）。对于大多数测试化合物，确定的MIC值在10μg/ ml MIC限度以下，该限度被认为可以界定有效的抗菌药物，或者与使用的阳性对照（四环素/制霉菌素）相当或更低。发现最易感的生物是金黄色葡萄球菌，MIC值甚至达到0.001μg/ ml。-CH（OH）（CH（2））（n）S-和-CH（= NOH）（CH（2））（n）S-（n
• Synthesis, spectral characterization, electrochemical properties and antimicrobial screening of sulfur containing acylferrocenes
  作者：Danijela Ilić、Ivan Damljanović、Dragana Stevanović、Mirjana Vukićević、Niko Radulović、Volker Kahlenberg、Gerhard Laus、Rastko D. Vukićević

  DOI：10.1016/j.poly.2010.03.002

  日期：2010.5

  Several known and eight new sulfur containing acylferrocenes of the general formula FcCO(CH2)(n)SR (where Fc = ferrocenyl, n = 1 or 2 and R = alkyl, 4-bromobenzyl or 2,6-dichlorobenzyl group) were synthesized in order to test their in vitro antimicrobial activity against 11 bacterial and three fungal/yeast strains. It has been shown that only four of the 14 ketones are completely inactive at the tested dose, while the activities of the other ones were noteworthy. All new compounds were well characterized by IR and NMR spectral data, and their electrochemical properties were investigated by cyclic voltammetry. The X-ray crystal structures of two representative ketones are also presented. (C) 2010 Elsevier Ltd. All rights reserved.
• Syntheses and crystal structures of (E)/(Z)-isomers of 1-ferrocenyl-1-hydroxyimino-3-thiabutane and 1-ferrocenyl-1-hydroxyimino-4-thiapentane
  作者：Mirjana D. Vukićević、Klaus Wurst、Adrian G. Müller、Gerhard Laus、Rastko D. Vukićević

  DOI：10.1016/j.poly.2004.12.013

  日期：2005.3

  Four new potential bidentate ligands - oximes of ferrocenyl ketones containing sulfur in their side chains [(E)-, and (Z)-(eta(5)-C5H5)Fe(eta(5)-C5H4)-C(=NOH)-(CH2)(n)-SCH3, n = 1 or 2] were synthesised and characterized by IR, H-1 and C-13 NMR spectral data. Single crystal X-ray structure determinations of these compounds are also reported. (c) 2005 Elsevier Ltd. All rights reserved.