Production of 5-hydroxy-7-methoxy-4-methylphthalide in a culture of Penicillium crustosum

figure 3 1H NMR spectrum of 5-hydroxy-7-methoxy-4-methylphthalide (400 MHz, DMSO). 

The ¹H NMR spectrum of 5-hydroxy-7-methoxy-4-methylphthalide (Figure 3) showed signals for methyl group at δ 1.95 (H-9, singlet, 3H), a signal for the methoxyl group at δ 3.79 (H-8, singlet, 3H), a signal corresponding to one methylene group at δ 5.15 (H-3, singlet, 2H), and a signal for aromatic hydrogen at δ 6.49 (H-6, singlet, 1H).

Figure 1 Structures of the compounds mycophenolic acid and 5-hydroxy-7-methoxy-4-methylphthalide. 

TABLE I 1H, 13C and gHMBC NMR data for the compounds mycophenolic acid and 5-hydroxy-7methoxy-4methylphthalide 

Position		Mycophenolic acid		5-hydroxy-7methoxy-4methylphthalide
	δ 13C	δ 1H(multiplicity, J in Hz)	1H-13C gHMBC*	δ 13C	δ 1H(multiplicity, J in Hz)	1H-13C gHMBC *
1	173.0	-		173.0	-	-
3	70.0	5.18 (2H, br s)	1; 3a	68.0	5.15 (2H, br s)	1; 3a; 4; 5; 7; 7a
3a	122.1	-	-	104.0	-	-
4	116.7	-	-	110.0	-	-
5	163.7	-	-	163.0	-	-
6	106.4	-	-	98.0	6.49 (1H, s)	1; 4; 5; 7; 7a
7	153.7	-	-	158.0	-	-
7a	144.0	-	-	151.0	-	-
8	61.0	3.74 (3H, s)	5	57.0	3.79 (3H, s)	7
9	11.5	2.13 (3H, s)	3; 3a; 4; 5	11.0	1.95 (3H, s)	3a; 4; 5
OH	-	7.67 (1H, br s)	-	-	10.59 (1H, br s)	4; 6; 5
1’	179.1	-	-	-	-	-
2’	32.7	2.38-2.47 (2H,m)	1’; 3’; 4’	-	-	-
3’	34.2	2.24-2.32 (2H,m)	1’; 2’; 4’; 5’; 7’	-	-	-
4’	133.9	-	-	-	-	-
5’	123.0	5.23-5.28 (1H,m)	3’; 7’	-	-	-
6’	22.3	3.37 (2H, br d; 6.8)	5; 7; 5’	-	-	-
7’	16.1	1.78 (3H, s)	3’; 4’; 5’		-	-

Abbreviations: s - singlet, br s - broad singlet, br d - broad doublet, m - multiplet.

Figure 2 1H NMR spectrum of mycophenolic acid (400 MHz, CDCl₃). 

The ¹H NMR spectrum of the mycophenolic acid (Figure 2) showed signals for a methyl group at δ 1.78 (H-7', singlet, 3H) and a methyl group linked to aromatic ring at δ 2.13 (H-9, singlet, 3H), a signal for a methoxyl group at δ 3.74 (H-8, singlet, 3H), two signals corresponding to aliphatic methylenes in the region of δ 2.47 to δ 2.38 (H-3a' and H-3b', multiplet 2H), of δ 2.32 to δ 2.24 (H-2', multiplet, 2H), a broad doublet for a methylene group at δ 3.37 (H-6', 2H), a broad singlet at δ 5.18 (H-3, 2H) referring to an aliphatic methylene bearing oxygen, and a multiplet for a methyne group of δ 5.23 to δ 5.28 (H-5',1H).

Figure 4 gHMBC NMR experiment of 5-hydroxy-7-methoxy-4-methylphthalide (400 MHz, DMSO) and important long range correlations detected. 

Anais da Academia Brasileira de Ciências

Print version ISSN 0001-3765

An. Acad. Bras. Ciênc. vol.85 no.2 Rio de Janeiro Apr./June 2013 Epub June 17, 2013

http://dx.doi.org/10.1590/S0001-37652013005000024 

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Synthesis of 1- (1-adamantyl) -3,4,5-trinitro-1H-pyrazole.

Synthesis of 1- (1-adamantyl) -3,4,5-trinitro-1H-pyrazole.

To 1.5 g (0.00739 mol) of 3,4,5-trinitro-1H-pyrazole in 20 ml of diethyl ether at 0 ° C was added dropwise a solution of 1 g (0.00739 mol) of 1,3-svezhevozognannogo dehydroadamantane in 20 ml of diethyl ether. The mixture was kept under stirring for 1 hour at 0 ° C, the temperature was raised why to reflux and held for an additional 3 hours. The solvent was distilled off. The product was purified by recrystallization from ethanol.

Yield 2.44 g (98%). Mp = 139-140 ° C.

Mass spectrum, m / z (intensity,%): 337 (M ⁺ , 2%), 292 ([M-NO ₂ ] ⁺ , 2%), 247 (2%), 245 ([M- (NO ₂ ) ₂ ] +, 2%), 199 ([M-3NO ₂ ] ⁺ , 2%), 177 (36%), 151 (21%), 150 (48%), 135 (Ad ⁺ , 96%), 121 (48%), 107 (56%) 95 (71%), 93 (100%) 67 (45%) 55 (75%).

NMR ¹ H (300 MHz, DMSO-d ₆ ), δ, ppm .: 1.66 (6H, CH ₂ , H _delta -Ad), with 2.1 (3H, CH, H _y -Ad), 2.18 to (6H, CH ₂ , H _beta -Ad).

NMR ¹³ C (75.47 MHz, CDCl ₃ ), δ, ppm .: 71.8872 (s, 1C, C _alpha -Ad), 41.0302 (s, 3C, C _beta -Ad), 35.2616 (s, 3C, C _delta -Ad), 29.9234 (s, 3C, C _y -Ad).

A process for production of 1- (1-adamantyl) -3,4,5-trinitro-1H-pyrazole (RU 2528404):

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5-(hydroxymethyl)-2-furaldehyde

R_f 0.55 (ethyl acetate:hexane = 2:1)

Mp.: 28˚C - 32˚C (lit.: 31˚C - 32˚C [6] ). 

IR ν_max (KBr, cm⁻¹): 3405, 3123, 2926, 2851, 1675, 1523, 1397, 

1370, 1334, 1280, 1192, 1023. 

¹H NMR (800 MHz, DMSO-d₆) δ_H 4.51 (d, 2H, J = 6.0 Hz, CHO); 

5.59 (t, 1H, J = 6.0 Hz, OH); 6.61 (d, 1H, J = 3.5 Hz, H-4); 7.50 (d, 1H, J = 3.5 Hz, H-3); 9.55 (s, 1H, CH=O). 

MS(EI): 126 (C₆H₆O₃). EI-MS (rel. int.%): 126(96); 109(10); 97(100); 81(4); 

69(24); 53(9); 41(50); 39(22).

HPLC spectrum

Machine type: Agilent 1260 Infinity LC

Column: Agilent ZORBAX-C18, 4.6mm×150mm

Mobile phase: methanol:water=5:95(0 min)-100:0(15 min), gradient elution

Flow rate: 1 ml min-1

Measurement temperature: room temperature

Detector: UV, wavelength at 278 nm

Sample concentration: 0.5 g L-1

FT-IR spectrum

Measurement type: BRUKER TENSOR 27

Method: KBr pellet

Sample: 10mg HMF:150mg KBr

Wavelength range: 400-4000cm-1

1H-NMR spectrum

Machine type: 400MHz AVANCE III

Sample weight: 30mg

Solvents:CDCl3

13C-NMR spectrum

Machine type: 400MHz AVANCE III

Sample weight: 30mg

Solvent: CDCl3

Frequency: 100.6 MHz

五、The main derivatives of HMF:

Major application fields:

The main application of 5-hydroxymethylfurfual  is as platform chemicals.  Now, HMF  can be  synthesized  fragrance  as a precursor substance.  In addition, HMF can be used in  fine  chemicals   synthesis,  including  pharmaceuticals,  agrochemicals,   macrocycles,  heterocycles,  sugar   derivatives.  In the future,  the main  application  is  to  substitute  oil  to produce  biofuel and  bio-based polymers  as precursor.

...................

Hydroxymethylfurfural
IUPAC name[hide] 5-(hydroxymethyl)-2-furaldehyde
Identifiers
CAS number	67-47-0
ChemSpider	207215
KEGG	C11101
ChEBI	CHEBI:412516
ChEMBL	CHEMBL185885
Jmol-3D images	Image 1
SMILES [show]
InChI [show]
Properties
Molecular formula	C6H6O3
Molar mass	126.11 g/mol
Density	1.29 g/cm3
Melting point	30 to 34 °C (86 to 93 °F; 303 to 307 K)
Boiling point	114 to 116 °C (237 to 241 °F; 387 to 389 K) (1 mbar)
λmax	282 nm[1]
Related compounds
Related furan-2-carbaldehydes	Furfural Methoxymethylfurfural
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

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