3-Ferrocenyl-4-(4-hydroxyphenyl)-hex-3-ene

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Molecules 2014, 19(7), 10350-10369; doi:10.3390/molecules190710350
http://www.mdpi.com/1420-3049/19/7/10350/htm


3-Ferrocenyl-4-(4-hydroxyphenyl)-hex-3-ene (4) 
Zinc powder (1.82 g, 27.9 mmol), titanium tetrachloride (2.04 mL, 18.6 mmol), propionylferrocene (1.13 g, 4.65 mmol), p-hydroxypropiophenone (0.70 g, 4.65 mmol). After column chromatography followed by preparative HPLC (acetonitrile/water 90/10), and recrystallization from a pentane/diethylether, 4 was obtained as orange crystals (0.50 g, 30% yield) consisting of a mixture of Z and E isomers (63/37). 

1H-NMR (300 MHz, CDCl3): 
δ 0.92 (t, J = 7.5 Hz, 3H, CH3), 
1.24 (t, J = 7.5 Hz, 3H, CH3), 
2.28 and 2.41 (q, J = 7.5 Hz, 2H, CH2), 
2.53 and 2.61 (q, J =7.5 Hz, 2H, CH2), 
3.70 and 4.24 (s, 2H, C5H4), 
3.97 and 4.35 (s, 2H, C5H4), 
4.03 and 4.15 (s, 5H, Cp), 
4.70 and 4.72 (s, 1H, OH), 
6.77 and 6.82 (d, J = 8.5 Hz, 2H, C6H4), 6.90 and 7.00 (d, J = 8.5 Hz, 2H, C6H4). 


13C-NMR (75.4 MHz, CDCl3): 
δ 13.0 and 13.2 (CH3), 
15.3 and 16.0 (CH3), 
26.7 and 28.4 (CH2), 
28.8 and 29.5 (CH2), 
67.8 and 67.9 (2CH, C5H4), 
69.0 and 69.1 (2CH, C5H4), 
69.1 and 69.2 (5CH, Cp), 
77.4 (C, C5H4), 
115.1 and 115.2 (2CH, C6H4), 
130.1 and 130.5 (2CH, C6H4), 
133.3 (C), 137.1 and 137.2 (C), 138.0 (C), 153.8 and 153.9 (C). 

IR (KBr, ν cm−1): 3418 (OH), 3094, 3062, 2929, 2871 (CH2, CH3). 

MS (EI, 70 eV) m/z: 360 [M]+., 331 [M-Et]+, 295 [M-Cp]+, 121 [CpFe]+. MS (CI, CH4) m/z: 361 [M+H]+, 360 [M]+., 295. 

HRMS (ESI, C22H24FeO: [M]+.) calcd: 360.11765, found: 360.11711.






http://www.mdpi.com/1420-3049/19/7/10350/htm

Atypical McMurry Cross-Coupling Reactions Leading to a New Series of Potent Antiproliferative Compounds Bearing the Key [Ferrocenyl-Ene-Phenol] Motif

Pascal Pigeon 1,2, Meral Görmen 1, Konrad Kowalski 3, Helge Müller-Bunz 4, Michael J. McGlinchey 4, Siden Top 2,* and Gérard Jaouen 1,2,*

1

Chimie ParisTech, 11 rue Pierre et Marie Curie, Paris F75231 Paris cedex 05, France; E-Mails:pascal.pigeon@chimie-paristech.fr (P.P.); meralgormen@gmail.com (M.G.)

2

Sorbonne Universités, UPMC univ Paris 6, Institut Parisien de Chimie Moléculaire (IPCM) - UMR 8232, 4 place Jussieu, 75252 Paris Cedex 05, France

3

Faculty of Chemistry, Department of Organic Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland; E-Mail: konkow@chemia.uni.lodz.pl

4

UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4 Ireland; E-Mails: helge.muellerbunz@ucd.ie (H.M.-B.); michael.mcglinchey@ucd.ie (M.J.M.)

*

Authors to whom correspondence should be addressed; E-Mails: siden.top@upmc.fr (S.T.);gerard.jaouen@upmc.fr (G.J.); Tel.: +33-1-44-27-66-99 (S.T.); +33-1-43-26-95-55 (G.J.); Fax: +33-1-43-26-00-61 (S.T.); +33-1-43-26-00-61 (G.J.).

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