2,4-dimorpholinocyclopent-2-enone

1465003-25-1 cas

2,4-dimorpholinocyclopent-2-enone (1b):

1H NMR (300 MHz, CDCl3) 6.24 (d, J = 2.9 Hz, 1H, COC=CH), 3.78 (t, J = 4.7 Hz, 4H, morpholine), 3.73 (t, J = 4.7 Hz, 4H, morpholine), 3.73-3.72 (m, 1H, COCH2CHN), 3.15-3.14 (m, 4H, morpholine), 2.54-2.52 (m, 4H, morpholine), 2.49-2.48 (m, 1H, COCH2), 2.46-2.45 (m, 1H, COCH2);

13C NMR (75 MHz, CDCl3) 38.1, 48.1, 50.0, 60.3, 66.6, 67.1, 129.5, 151.7, 202.0.

Water excellent solvent for the synthesis of bifunctionalized cyclopentenones from furfural

M. Nardi,*ab  P. Costanzo,c  A. De Nino,a  M. L. Di Gioia,d  F. Olivito,c  G. Sindonaa  and  A. Procopioc 

*Corresponding authors

aDipartimento di Chimica, Università della Calabria, Cubo 12C, 87036-Arcavacata di Rende, Italy
E-mail: monica.nardi@unical.it
Fax: +39 0984493307
Tel: +39 0984 492850

bDipartimento di Agraria, Università Telematica San Raffaele, 247, Roma Via di Val Cannuta, Italy

cDipartimento di Scienze della Salute, Università Magna Graecia, Viale Europa, 88100-Germaneto, Italy

dDipartimento di Farmacia e Scienze della Salute e della Nutrizione, Edificio Polifunzionale, Università della Calabria, 87030 Arcavacata di Rende, Italy

Abstract

Chiral cyclopentenones are important precursors in the asymmetric synthesis of target molecules. In particular, C-2 amino cyclopentenones could be utilised as intermediates towards antitumor natural products. On the basis of our previous experience, we report an environmentally friendly protocol for the synthesis of bifunctionalized cyclopentenones in water from furfural. The use of water and MW gives high regioselectivity and good to excellent yields. The reaction can be realized in short times with various nucleophiles.

Monica Nardi

PostDoc

Università della Calabria , Rende · Dipartimento di Chimica e Tecnologie Chimiche - CTC

Università della Calabria

Department

• Dipartimento di Chimica e Tecnologie Chimiche - CTC

• Research experience

  • Oct 2014–present

    Visiting Lectur

    The School of Pharmacy · School of Pharmacy · Prof Steve Brocchini
    United Kingdom · London
  • Jan 2014–present

    PostDoc Position

    Università della Calabria · Department of Pharmacy, Health and Nutritional Sciences
    Italy · Rende
  • Mar 2001–Sep 2014

    PostDoc

    Università della Calabria · Department of Management
    Italy · Rende
  • Mar 2001–Dec 2013

    PostDoc Position

    Università della Calabria · Dipartimento di Chimica e Tecnologie Chimiche - CTC · Prof Giovanni Sindona
    Italy · Rende

Dipartimento di Chimica, Università della Calabria

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1 Estevão, Mónica S.; Afonso, Carlos A.M.; Tetrahedron Letters; vol. 58; nb. 4; (2017); p. 302 - 304

2  Green Chemistry; vol. 19; nb. 1; (2017); p. 164 - 168



“ORG SPECT INT” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

Ethyl(E)-3-(4-methoxyphenyl)acrylate

ethyl(E)-3-(4-methoxyphenyl)acrylate (Table 4, entry 3):

The product was purified with column chromatography on silica gel 60-120 mesh (hexane/ethyl acetate= 9:1) as a white solid; yield 88 % (165 mg);

mp 74-76C;

1H NMR (CDCl3 , 200 MHz):  7.55 (d, 1H, J=15.9 Hz), 7.40-7.43 (d, 2H, J=6 Hz), 6.81-6.84 (d, 2H, J=6 Hz), 6.21 (d, 1H, J=15.9 Hz), 4.16 (q, 2H, J=7.1 Hz), 3.73 (s, 3 H), 1.24 (t, 3H, J=7.1 Hz);

13C NMR (CDCl3 , 50 MHz): 167.3, 161.3, 144.2, 129.7, 127.7, 127.2, 115.8, 114.3, 60.3, 55.3, 14.4 ppm;

MS (ESI) C12H14O3 : m/z 206.

(E)-ethyl 3-(4-methoxyphenyl)acrylate

13C NMR PREDICT

An Efficient Palladium Catalyzed Mizoroki-Heck Cross-Coupling in Water

Green Chem., 2017, Accepted Manuscript
DOI: 10.1039/C7GC02869E, Paper

Sanjay Jadhav, C. V. Rode
The homogeneous Pd-catalysed Mizoroki-Heck coupling reaction has been successfully conducted in water in the absence of any additives under aerobic condition. The various key reaction parameters that affect the yield...

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“ORG SPECT INT” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

Problem, [(E)-hex-2-en-2-yl]benzene

Molecular Formula:	C12H16
Molecular Weight:	160.26 g/mol

 [(E)-hex-2-en-2-yl]benzene

NMR IS EASY

MOM CAN TEACH

13 CNMRPREDICT

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CC(C)c1ccc(cc1CC(=O)O)C=O

“ORG SPECT INT” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent


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C/C(=C\CCC)c1ccccc1

4-methyl-2-phenylbenzoxazole

4-methyl-2-phenylbenzoxazole

77791-11-8

4-methyl-2-phenylbenzoxazole (2b) [ref] White solid, 39mg, isolated yield 94%. 1H NMR (400 MHz, CDCl3) δ 8.17 (dd, J = 6.6, 3.0 Hz, 2H), 7.49 – 7.37 (m, 3H), 7.30 (d, J = 8.0 Hz, 1H), 7.14 (t, J = 7.7 Hz, 1H), 7.04 (d, J = 7.5 Hz, 1H), 2.59 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 162.2, 150.4, 141.3, 131.2, 130.5, 128.8, 128.7, 128.7, 127.5, 127.3, 124.9, 124.6, 107.8, 16.5.

X. Meng, Y. Wang, Y. Wang, B. Chen, Z. Jing, G. Chen, P. Zhao, J. Org. Chem., 2017, 82, 6922.

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OMS-2/H2O2/Dimethyl Carbonate: An Environmentally-Friendly Heterogeneous Catalytic System for Oxidative Synthesis of Benzoxazoles at Room Temperature

Xu Meng,a Yuanguang Wang,a Baohua Chen,b Gexin Chen,a Zhenqiang Jing,c Peiqing Zhaoa,* a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, China. Fax: + 96 931 8277008; Tel: + 86 931 4968688; E-mail: xumeng@licp.cas.cn; zhaopq@licp.cas.cn b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China c Suzhou Institute of Nano-Tech and Nano-Bionic (SINANO), Chinese Academy of Sciences, Suzhou 215123, China

CC1=C2C(=CC=C1)OC(=N2)C3=CC=CC=C3

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Problem, 2-(5-formyl-2-isopropylphenyl)acetic acid

2-(5-formyl-2-isopropylphenyl)acetic acid

13 C NMR PREDICT

NMR IS EASY

MOM CAN TEACH

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CC(C)c1ccc(cc1CC(=O)O)C=O

“ORG SPECT INT” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

4-(6-Benzoxazoyl)morpholine

4-(6-Benzoxazoyl)morpholine

1 H NMR (600 MHz, CDCl3) δ 8.23 (s, 1H), 7.83 (d, J = 8.3 Hz, 1H), 7.71 (s, 1H) 7.44 (d, J = 7.6 Hz, 1H), 4.00–3.25 (br, 8H).

13C NMR (150 MHz, CDCl3) δ 169.52, 153.87, 149.67, 141.24, 132.90, 123.79, 120.76, 110.48, 66.81.

HRMS (DART) m/z calcd for C12H13N2O3 [MH]+ : 233.0926, found 233.0926.

4-(6-Benzoxazoyl)morpholine (8) ( 13C NMR, 150 MHz, CDCl3)

4-(6-Benzoxazoyl)morpholine (8) ( 1 H NMR, 600 MHz, CDCl3)

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NMR PROBLEM, 3-ethoxy-2,5-dimethylhex-4-enenitrile

3-ethoxy-2,5-dimethylhex-4-enenitrile

NMR IS EASY

MOM CAN TEACH

13C NMR PREDICT

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“ORG SPECT INT” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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C/C(C)=C/C(OCC)C(C)C#N