Diphenyl selenide

25 MHz ¹³C NMR spectrum of diphenyl selenide in CDCl₃.

  Figure shows the fully coupled and decoupled ¹³C NMR spectra of diphenyl selenide. Although the large ¹J_C-H splittings are easy to identify, the fine structure of the individual multiplets is not first order (e.g., only the para carbon has an approximately centrosymmetric pattern, the others do not). This is because we are looking at the X part of an AA'BB'CXpattern (^JABC^j are protons, X is carbon). Since the AA' and BB' parts are strongly coupled, we see the usual complex effects of "virtual coupling" on the X resonance  When noise {¹H} decoupling is applied, the spectrum becomes much more intense, and only 4 lines remain, one for each carbon.

  In this compound we have a second magnetically active nucleus (⁷7Se, natural abundance 7.5%, I = 1/2), so each of the ¹³C peaks has ⁷7Se satellites, although coupling between C-4 and the selenium is too small to detect (the satellites are under the main peak).

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Abstract: The title compound, ethyl 3-{2-[(3-methyl-1H-indol-2-yl)carbonyl]hydrazinylidene} butanoate (3), was prepared via reaction of 3-methyl-1H-indole-2-carbohydrazide (1) and ethyl 3-oxo­butanoate (2) under reflux. The structure of the synthesized compound was assigned on the basis of elemental analysis, IR, 1H-NMR, mass spectral and X-ray data.




http://www.mdpi.com/1422-8599/2012/1/M749

Molbank 2012, 2012(1), M749; doi:10.3390/M749

Short Note

Ethyl 3-{2-[(3-Methyl-1H-indol-2-yl)carbonyl]­hydrazinylidene}­butanoate

Thoraya A. Farghaly and Sobhi M. Gomha * 

 E-Mail: s.m.gomha@hotmail.com.

Department of Chemistry, Faculty of Science, University of Cairo, Giza 12613, Egypt

* Author to whom correspondence should be addressed.

DR SOBHI M GOMHA - UNIVERSITY OF CAIRO

http://cu.edu.eg/ar/Home

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Synthesis of Ethyl 3-{2-[(3-Methyl-1H-indol-2-yl)carbonyl]hydrazinylidene}butanoate (3)

A mixture of the hydrazide 1 (1.89 g, 10 mmol) and ethyl 3-oxobutanoate 2 (10 mmol) in absolute

ethanol (20 mL) was heated at reflux temperature for 2 h. The reaction mixture was then cooled and

the formed precipitate was filtered off, washed with ethanol to afford the title compound 3. Yield:

84%; yellow microcrystals (from ethanol); mp: 238–240 °C.

 IR (KBr): v 1706, 1668 (2 C=O), 3409,3234 (2 NH) cm−1

1H NMR (DMSO-d6): δ 1.24 (t, J = 7.0 Hz, 3H, CH3), 2.03 (s, 3H, CH3), 2.53 (s,

3H, CH3), 3.43 (s, 2H, CH2), 4.23 (q, J = 7.0 Hz, 2H, CH2), 6.87–7.98 (m, 4H, ArH ), 10.38 (s, 1H,

D2O exchangeable, NH), 11.21 (s, 1H, D2O exchangeable, NH). 

MS m/z (%): 301 (M+, 42), 189 (100),155 (318), 117 (46), 77 (21).

Anal. Calcd for C16H19N3O3 (301.34): C, 63.77; H, 6.36; N, 13.94. Found C, 63.39; H, 6.46; N, 13.65.

References and Notes

1. Ismail, M.F.; Shmeiss, N.A.M.M.; El-Diwani, H.I.; Arbid, M.S. Synthesis and pharmacological

activity of some 2,3-diphenylindole derivative. Indian J. Chem. Sect. B 1997, 36B, 288–292.

2. von Angerer, E.; Knebel, N.; Kager, M.; Ganss, B.J. 1-(Aminoalkyl)-2-phenylindoles as novel

pure Estrogen Antagonists. J. Med. Chem. 1900, 33, 2635–2640. 

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STATAN A

Example 4

Structural elucidation of Statan A

Accurate mass analysis was done on a Agilent HP 1100 liguid chromatograph with a diode array detector (DAD) coupled to a LCT Micromass oaTOF instrument with Z-spray electro spray source (ESI) and a lockspray probe. 1 microL of sample was injected on an Agilent Hypersil BDS-C₁₈ 125x2 mm column with 3 micro m particles. A water-acetonitrile gradient, starting with 15% acetonitrile-water going to 100% acetonitrile in 40 min, maintaining 100% acetonitrile for 5 min, before returning to the start conditions in 8 min equilibrating for 5 min. TFA, 50 ppm was added to the water. 

The MS was operated in the positive ESI mode using leucineenkephalin as lockmass ([M+H]+ ion at 556.2771 Da/e). The molecular ion of protonated Statan A appeared at 301.1421 corresponding to the composition C₁₈H₂₀O₄ (Δ -6.3 ppm) corresponding to 9 DBE.

NMR spectra of statans were recorded in 5 mm tubes at 600.13 MHz for ¹H and at 150.92 MHz for ¹³C and at 300 K, using DMSO-cf₆, on a Bruker DRX 600 according to Larsen et al. ,2001, (J Agricult and Food Chem 49: 5081-5084). The ¹³C and the C.H-COSY spectra revealed the presence of one methyl, four methylene, and two methine groups, together with 5 aromatic protons, two hydroxy protons (9.95 and 5.20 ppm), 5 quartemary aromatic carbon atoms and finally a carboxy group at 170.2 indicating an ester or lactone. 

The ¹H and H,H- COSY spectra revealed the presence of one aliphatic (-CH₂-CHOH-CH₂-CH-CH₂-CH₂-) and two aromatic spin systems (AB and ABC) together with a single methyl group. Interpretation of the heteronuclear multiple bond coherence spectrum (HMBC) established the structure of Statan A.

 The chemical shift values of the carbons in the naphthalene part of the molecule were very similar to the values of the model compound 7,8-dimethyl-1-naphtol (Jung, K.-Y., Koreeda, M., 1989, J Organic Chem 54: 5667-5675) and similarly the chemical shift values of the aliphatic part of the molecule were very similar to those reported for solistatin (Sørensen et al., 1999, Phytochemistry 51 : 1027-1029) and other statins, altogether strongly supporting the proposed structure.

¹H NMR (DMSO-d6): δ 9.95 (1 H, bs, 8'-OH), 7.54 (1 H, d, J = 8.2 Hz, H-4'), 7.24 (1 H, d, J = 8.2 Hz, H-3'), 7.24 (1 H, d, J = 7.9 Hz, H-5'), 7.16 (1 H, dd, J = 7.9 and 7.5 Hz, H-6'), 6.83 (1 H, d, J = 7.5 Hz, H-7'), 5.20 (1 H, br s, 3-OH), 4.72 (1 H, m, 5-H), 4.16, br s, 3-H), 3.45 (1 H, br s, H-7a), 3.36 (1H, br s, H-7b), 2.68 (1 H, dd, J = 17.2 and 4.7 Hz, H-2a), 2.44 (3H, s, Me), 2.43 (1 H, d m, 17.2 Hz, H-2b), 1.92 (2H, m, H-6), 1.91 (1 H, m, H-4a), 1.79 (1 H, ddd, 14.3, 11.7 and 3.3 Hz, H-4b).

¹³C NMR (DMSO-d6): δ 170.2 (C-1), 154.8 (C-8"), 135.1 (C-1')_F 135.1 (C-4'a), 132.1 (C-2'), 129.0 (C-3'), 125.8 (C-4'), 124.7 (C-6'), 123.1 (C-8'a), 119.5 (C-5'), 109.9 (C-7'), 75.5 (C-5), 61.0 (C-3), 38.5 (C-2), 36.5 (C-6), 34.8 (C-4), 27.0 (C-7), 19.5 (Me).

http://www.google.com/patents/WO2003048148A2?cl=en

3-[(S)-1 -(4-bromophenyl)ethyl]-Trans-9-hydroxy-1 -oxa-3- azaspiro[5.5]undecan-2-one.

Sodium borohydride (47 mg) is added to 3-[(S)-1 -(4-bromo-phenyl)-ethyl]-1 -oxa-3- aza-spiro[5.5]undecane-2,9-dione (0.45 g) dissolved in tetrahydrofuran (4.5 mL) and water (0.6 mL) at room temperature. The mixture is stirred at room temperature for 2 h and then diluted with diethyl ether and acidified with 1 M aqueous hydrochloric acid. The organic phase is separated, washed with aqueous K₂CO3 solution and brine, and dried (Na₂SO₄). The solvent is evaporated and the residue is submitted to HPLC on reversed phase (methanol/water) to give the title compound in a ca. 9:1 mixture with 3-[(S)-1 -(4-bromophenyl)ethyl]-frans-9-hydroxy-1 -oxa-3- azaspiro[5.5]undecan-2-one. Yield: 0.25 g (55% of theory); LC (method 1 ): t_R= 3.42 min; 

Mass spectrum (ESI⁺): m/z = 368/370 (Br) [M+H]⁺; 

¹H NMR (400 MHz, DMSO- d₆) δ 1 .33-1 .55 (m, 4H) superimposed on 1 .47 (d, J = 7.1 Hz, 3H), 1 .55-1 .87 (m, 6H), 2.66-2.76 (m, 1 H), 3.13-3.22 (m, 1 H), 3.45 (m_c, 1 H), 4.53 (d, J = 4.5 Hz, 1 H), 5.44 (q, J = 7.1 Hz, 1 H), 7.25 (d, J = 8.4 Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H).

http://www.google.com/patents/EP2585444A1?cl=en

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