1-ferrocenyl-4-thiapentan-1-one | 360774-29-4

• 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-4-thiapentan-1-one
• 英文别名: 1-ferrocenyl-3-(methylthio)propan-1-one；FcC(O)CH2CH2SMe；cyclopenta-1,3-diene;1-cyclopenta-1,3-dien-1-yl-3-methylsulfanylpropan-1-one;iron(2+)
• CAS: 360774-29-4
• 化学式: C₁₄H₁₆FeOS
• 分子量: 288.193
• InChiKey: GBUDUENLZOWUOQ-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-4-thiapentan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96.3%的产率得到1-ferrocenyl-3-(methylsulfanyl)propan-1-ol
  参考文献：
  名称：

  含硫的二茂铁醇和肟：新的有希望的抗葡萄球菌药物。

  摘要：

  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

  DOI：

  10.1002/cbdv.201200029
• 作为产物：
  描述：

  二茂铁 、 3-(甲基硫代)丙酸 在 三氯化磷 、 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-ferrocenyl-4-thiapentan-1-one
  参考文献：
  名称：

  含硫的二茂铁醇和肟：新的有希望的抗葡萄球菌药物。

  摘要：

  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

  DOI：

  10.1002/cbdv.201200029

文献信息

• 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.
• Synthesis, characterization, and nucleophilic substitutions of dimethyl(2-ferrocenoylethyl)sulfonium iodide
  作者：Anka Pejović、Ivan Damljanović、Dragana Stevanović、Danijela Ilić、Mirjana Vukićević、Goran A. Bogdanović、Rastko D. Vukićević

  DOI：10.1016/j.tetlet.2013.06.130

  日期：2013.8

  Dimethyl(2-ferrocenoylethyl)sulfonium iodide was synthesized by reacting 1-ferroceny1-4-thiapentan-1-one with iodomethane and characterized from spectral data and single crystal X-ray structure analysis. This compound was capable of reacting with different N-, S-, and O-nucleophiles giving the corresponding beta-functionalized ferrocene-containing ketones. Furthermore, dimethyl sulfide can be displaced from the dimethyl(2-ferrocenoylethyl)sulfonium ion with cyanide or carbanions derived from 1,3-bifunctional compounds and nitropropane, leading to products with a new carbon-carbon bond. (C) 2013 Elsevier Ltd. All rights reserved.
• 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
  作者：Milan M. Milutinović、Petar P. Čanović、Dragana Stevanović、Romana Masnikosa、Milan Vraneš、Aleksandar Tot、Milan M. Zarić、Bojana Simović Marković、Maja Misirkić Marjanović、Ljubica Vučićević、Maja Savić、Vladimir Jakovljević、Vladimir Trajković、Vladislav Volarević、Tatjana Kanjevac、Ana Rilak Simović

  DOI：10.1021/acs.organomet.8b00604

  日期：2018.11.26

  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.