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Friday, 20 October 2017

Ethyl(1R,2S,3S,4S)-2-(furan-2-yl)-3-nitro-6-oxobicyclo[2.2.2]octane-1-carboxylate



Ethyl(1R,2S,3S,4S)-2-(furan-2-yl)-3-nitro-6-oxobicyclo[2.2.2]octane-1-carboxylate


Compound 7 Ethyl(1R,2S,3S,4S)-2-(furan-2-yl)-3-nitro-6-oxobicyclo[2.2.2]octane-1-carboxylate To a solution of CAT 10 (128 mg, 0.37 mmol) and the nitroolefin 9 (3.1 g, 22.3 mmol) in 10 mL anhydrous CH2Cl2 at room temperature was added enone 8 (1.8 g, 10.7 mmol). The resulting mixture was stirred at the same temperature until enone 8 is consumed as indicated by TLC. Then DBU (0.34 mL, 3.20 mmol) was added and the mixture was allowed to stir at ambient temperature until completion as indicated by TLC. The solution was concentrated in vacuo and purified by flash chromatography on silica gel (Hexane / EtOAc = 20 / 1) to give 7 (2 g, 61% yield) as a yellow solid. [α]D 23 28.0 (c = 1.0, CHCl3).

1H NMR (400 MHz, CDCl3): δ 7.29 (d, J = 0.8 Hz, 1H), 6.27 (dd, J = 2.0 Hz, J = 3.2 Hz, 1H), 6.14 (d, J = 4.0 Hz, 1H), 4.93 (m, 1H), 4.57 (d, J = 4.4 Hz, 1H), 4.11 (m, 2H), 3.04-3.02 (m, 1H), 2.80-2.75 (m, 1H), 2.60- 2.54 (m, 1H), 2.33-2.29 (m, 1H), 1.88-1.72 (m, 2H), 1.33-1.23 (m, 1H), 1.21 (t, J = 7.2 Hz, 3H).

13C NMR (100 MHz, CDCl3): δ 204.1, 168.7, 151.8, 142.5, 110.5, 108.1, 88.3, 61.3, 56.3, 42.0, 40.8, 33.7, 26.9, 19.2, 13.8.

IR (thin film): 3435, 3141, 3120, 2996, 2959, 1715, 1653, 1621, 1557, 1505, 1473, 1443, 1408, 1371, 1336, 1301, 1336, 1301, 1270, 1236, 1142, 1120, 1083, 1062, 1074, 1045, 1045, 1011, 996, 960, 930, 892, 884, 867, 803, 753, 628, 600, 508, 436 cm-1 .

LRMS (ESI): 308.0 (M+H)+ , 330.0 (M+Na)+ .

 HRMS (ESI): calcd for C15H18O6N (M+H) + : 308.1129. Found: 308.1130.

 Melting point: 117-118 oC.


Concise asymmetric total synthesis of (−)-patchouli alcohol

 Author affiliations

Abstract

The asymmetric total synthesis of (−)-patchouli alcohol was accomplished in a concise manner. Key reactions include a highly diastereo- and enantioselective formal organocatalytic [4 + 2] cycloaddition reaction, a radical denitration reaction, and an oxidative carboxylation reaction. The formal synthesis of norpatchoulenol was achieved as well.
Graphical abstract: Concise asymmetric total synthesis of (−)-patchouli alcohol

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Thursday, 19 October 2017

2-Methyl-3-tosyl-1,2,3,4-tetrahydroquinazoline

Image result for NMR IN COLOUR



Two-dimensional proton–proton NMR correlation spectrum of 2-methyl-3-tosyl-1,2,3,4-tetrahydroquinazoline in acetone-d6. A colour code was used to highlight the observed H–H couplings.



image file: c6ra20886j-s2.tif


Scheme 2 Pd-mediated hydrolysis of triethylamine in the presence of 2-tosylaminomethylaniline (HATs) to yield 2-methyl-3-tosyl-1,2,3,4-tetrahydroquinazoline and di(acetato)bis(diethylamine)palladium(II).

2-Methyl-3-tosyl-1,2,3,4-tetrahydroquinazoline

Yield = 12.3 mg (41%). 1H NMR (400 MHz, dmso-d6): δ/ppm 7.56 (d, J = 8.2 Hz, 2H, 2 × H-2′), 7.16 (d, J = 8.1 Hz, 2H, 2 × H-3′), 6.83 (m, 2H, H-5 + H-7), 6.46 (t, J = 7.1, 1H, H-6), 6.25 (d, J = 8.1 Hz, 1H, H-8), 6.09 (d, J = 3.4 Hz, 1H, NH), 5.22 (m, 1H, H-2), 4.54 (d, J = 17.2 Hz, 1H, CHH-4) and 4.36 (d, J = 17.2 Hz, 1H, CHH-4), 2.25 (s, 3H, CH3-4′) and 1.22 (d, 3H, J = 6.3 Hz, CH3-2). 1H NMR (250 MHz, CDCl3): δ/ppm 7.59 (d, J = 8.3 Hz, 2H, 2 × H-2′), 7.06 (d, J = 8.3 Hz, 2H, 2 × H-3′), 6.90 (t, 1H, H-7), 6.86 (d, 1H, H-5), 6.67 (dt, J = 7.5 and 1.1 Hz, 1H, H-6), 6.29 (d, J = 8.1 Hz, 1H, H-8), 5.36 (dq, J = 6.4 and 1.0 Hz, 1H, H-2), 4.70 (d, J = 17.4 Hz, 1H, CH2-4), 4.47 (d, J = 17.4 Hz, 1H, CH2-4), 2.29 (s, 3H, CH3) and 1.40 (d, J = 6.4 Hz, 3H, CH3). 13C NMR (62.5 MHz, CDCl3): δ/ppm 143.2 (C4′), 139.7 (C8a), 136.2 (C1′), 129.0 (2 × C3′), 127.6 (C5), 127.3 (2 × C2′), 126.4 (C7), 118.8 (C6), 116.9 (C4a), 116.4 (C8), 61.4 (CH), 41.8 (CH2), 21.5 (CH3) and 21.4 (CH3). IR (KBr, cm−1): 3387(s) ν(NH) cm−1, 1326(s) νas(SO2), 1158(vs) νs(SO2). MS (ESI) m/z = 325 (MNa+). HRMS calcd for C16H18N2NaO2S (MNa+): 325.0981; found, 325.0967. Elemental analysis (found): C 63.5, H 5.8, N 9.1; S, 10.5%. Calc. for C16H18N2O2S: C, 63.6; H, 6.0; N, 9.3; S, 10.6%.




http://pubs.rsc.org/en/content/articlehtml/2016/RA/C6RA20886J


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NMR PRESENTATION


NMR PRESENTATION





PHTHALAN




Phtalan

PHTHALAN


PHTHALAN.png
1H NMR PREDICT



13C NMR PREDICT






Phthalane is a bicyclic aromatic organic compound. It is also known as isocoumaran, or 1,3-dihydro-2-benzofuran. Derivatives are found in the drug Citalopram, and drug candidate Lu 10-171. It can be oxidised to phthalic acid.
Phthalane
Phthalan-2D-skeletal.png
Names
IUPAC name
1,3-dihydroisobenzofuran
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.007.106
EC Number207-815-2
PubChem CID
Properties
C8H8O
Molar mass120.148
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


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N-carboxymethyl indoline




N-carboxymethyl indoline 

2,3-dihydrobenzo[b][1,4]dioxine





2,3-dihydrobenzo[b][1,4]dioxine

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Wednesday, 18 October 2017

2,3-dihydrobenzofuran

2,3-Dihydrobenzofuran 99%

2,3-Dihydrobenzofuran

  • CAS Number 496-16-2
     
  • Empirical Formula (Hill Notation) C8H8O
     
  • Molecular Weight 120.15
  •  Beilstein Registry Number 111928
     




http://www.rsc.org/suppdata/gc/c4/c4gc01822b/c4gc01822b1.pdfhttp://www.rsc.org/suppdata/gc/c4/c4gc01822b/c4gc01822b1.pdf


1H NMR




MASS
Image result for nmr 2,3-dihydrobenzofuran
IR



UV




1H NMRPREDICT


13C NMR PREDICT




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ISOIDIDE




Monday, 16 October 2017

Diethyl Isosorbide (DEI)

STR1 STR2 str3 str4
Diethyl Isosorbide (DEI): []D 20 +95.9 (c 1, in MeOH);
1H NMR (400 MHz; CDCl3; Me4Si):  4.63 (t, J = 4.2 Hz, 1H, H-4), 4.51 (d, J = 4.1 Hz, 1H, H-3), 4.06–3.90 (m, 5H, H- 1, H-2, H-5, H-6), 3.80–3.69 (m, 1H, CH2-OC-5), 3.63–3.49 (m, 4H, H-6, CH2-OC-5, CH2- OC-2), 1.23 ppm (dt, J = 17.8, 7.0 Hz, 6H, CH3CH2O-C-2, CH3CH2O-C-5);
13C NMR (101 MHz; CDCl3; Me4Si):  86.57 (C-3), 84.45 (C-2), 80.36 (C-5), 80.27 (C-4), 73.64 (C-1), 69.81 (C-6), 66.28 (CH2-O-C-5), 65.24 (CH2-O-C-2), 15.49 ppm (CH3-CH2OC-5), 15.44 (CH3-CH2OC-2);
MS (70 eV): m/z 202 (M+ , 6%), 157 (1), 113 (17), 89 (33), 69 (100), 57 (11), 44 (39).
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Isosorbide dimethyl ether


Image result for Isosorbide dimethyl ether
CAS Registry No.:5306-85-4
Molecular Formula:C8H14O4Molecular Weight:174.2
Image result for Isosorbide dimethyl ether SYNTHESIS
Image result for Isosorbide dimethyl ether SYNTHESIS

STR1 STR2

13 C NMR
22.53 MHz
C8 H14 O40.05 ml : 0.5 ml CDCl3
STR1 STR2

1H NMR
STR1 STR2

IR NEAT
STR1
RAMAN
STR2

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Wednesday, 11 October 2017

Total synthesis of (-)-aritasone via the ultra-high pressure hetero-Diels-Alder dimerisation of (-)-pinocarvone

STR1

Total synthesis of (-)-aritasone via the ultra-high pressure hetero-Diels-Alder dimerisation of (-)-pinocarvone

Org. Biomol. Chem., 2017, Advance Article
DOI: 10.1039/C7OB02204B, Paper
Maliha Uroos, Phillip Pitt, Laurence M. Harwood, William Lewis, Alexander J. Blake, Christopher J. Hayes
The total synthesis of aritasone via the proposed biosyntheic hetero-Diels-Alder [4 + 2] cyclodimerisation of pinocarvove, has been achieved under ultra-high pressure (19.9 kbar) conditions

Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone

Christopher Hayes

Abstract

This paper describes a total synthesis of the terpene-derived natural product aritasone via the hetero-Diels–Alder [4 + 2] cyclodimerisation of pinocarvove, which represents the proposed biosyntheic route. The hetero-Diels–Alder dimerisation of pinocarvone did not proceed under standard conditions, and ultra-high pressure (19.9 kbar) was required. As it seems unlikely that these ultra-high pressures are accessible within a plant cell, we suggest that the original biosynthetic hypothesis be reconsidered, and alternatives are discussed.
STR1 STR2
Aritasone (1) A solution of pinocarvone (()-2) (100 mg, 0.66 mmol) in dichloromethane (5 mL) was pressurized to 19.9 kbar for 120 h. The 1H NMR spectrum of the crude reaction mixture showed significant change in the composition as compared to the starting material. The solvent was evaporated and the residue was purified by column chromatography (pentane/Et2O; 25/1) to afford aritasone (1) (20 mg, 40%) as a white solid; mp 101- 103 C; (lit3 mp 105-106 °C); []D 26 26.1 (c 0.40 in CHCl3); (lit3 []D 9 118); max/cm-1 (CHCl3) 2926, 2359, 1722, 1689, 1601, 1467, 1372, 1305, 1152; H (400 MHz; CDCl3, 298 K) 2.67 (2H, app dd, J 4.8, 2.5, H-2a, H-2b), 2.45-2.32 (3H, m, H-7a, H-15a, H-3), 2.15-2.01 (4H, m, H-10, H-12, H-15b, H-16a), 1.91-1.80 (2H, m, H-4, H-16b), 1.66 (1H, ddd, J 13.8, 6.4, 3.4, H-7b), 1.38 (3H, s, CH3), 1.29-1.22 (7H, br s, CH3, H-13a, H-13b, H-8a, H- 8b), 0.90 (3H, s, CH3), 0.80 (3H, s, CH3); C (100 MHz; CDCl3, 298 K) 209.5 (C), 142.9 (C), 112.8 (C), 80.8 (C), 45.2 (CH), 44.3 (CH), 43.7 (CH2), 40.9 (CH), 40.5 (C), 39.4 (CH), 38.3 (C), 33.2 (CH2), 32.7 (CH2), 27.7 (CH3), 27.3 (CH2), 27.3 (CH3), 26.3 (CH3), 22.5 (CH2), 22.1 (CH2), 20.9 (CH3); HRMS m/z (ES+ ) found 301.2162 (M + H) C20H29O2 requires 301.2162 and 323.1981 (M + Na) C20H28O2Na requires 323.1982. These data were consistent to those previously reported, 5, 7 however the value of the specific rotation5 differs significantly from that measured during the original isolation work.3

Christopher Hayes

Contact

Biography

Prof. Christopher Hayes began his academic career here in Nottingham with his B.Sc. in July 1992. Remaining at Nottingham, he completed his Ph.D. studies in organic chemistry, under the supervision of Professor Gerald Pattenden, in September 1995. In January 1996, on a NATO Postdoctoral Fellowship, he moved to the University of California at Berkeley where he worked in the group of Professor Clayton H. Heathcock. In September 1997, he returned to Nottingham as a Lecturer in Organic Chemistry, and has subsequently been promoted to Reader (2003), Associate Professor (2006) and Professor of Organic Chemistry (2011).

Research Summary

Research is centred in main-stream synthetic organic chemistry, focusing on the organic chemistry of biologically active molecules. His current research interests span a number of areas such as (i)… read more

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