Home Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
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Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3

  • Ren-Song Chen , Jing-Jie Zhang , Yi Zhang , Chuan-Yan Xu and Jiang-Hai Ye EMAIL logo
Published/Copyright: February 24, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 3

Abstract

C20H32O3, monoclinic, P21 (no. 4), a = 7.8981(17) Å, b = 10.302(2) Å, c = 11.028(3) Å, β = 90.020(2)°, V = 897.3(3) Å3, Z = 2, R gt (F) = 0.0603, wR ref (F 2) = 0.1342, T = 273(2) K.

CCDC no.: 2221717

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.24 × 0.21 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 31.0°, 99%
N(hkl)measured, N(hkl)unique, R int: 5323, 4825, 0.019
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2583
N(param) refined: 213
Programs: Olex2 [1], Bruker [2], SHELX [3], Diamond [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
O1 0.6734 (3) 0.2919 (2) 0.3986 (2) 0.0530 (7)
C1 0.3929 (4) 0.4837 (3) 0.4476 (3) 0.0411 (9)
H1A 0.380995 0.412992 0.504986 0.049*
H1AB 0.333720 0.558234 0.480651 0.049*
C2 0.3081 (5) 0.4447 (4) 0.3289 (3) 0.0510 (9)
H2A 0.356020 0.363558 0.300538 0.061*
H2AB 0.188054 0.431422 0.342639 0.061*
O2 0.8512 (3) 0.4320 (2) 0.4890 (2) 0.0384 (6)
O3 0.9047 (4) 0.3847 (2) 0.7534 (2) 0.0559 (7)
H3 0.882811 0.361071 0.684114 0.084*
C3 0.3325 (5) 0.5482 (4) 0.2333 (4) 0.0515 (10)
H3A 0.280874 0.628338 0.261039 0.062*
H3AB 0.274820 0.521785 0.159642 0.062*
C4 0.5202 (5) 0.5734 (4) 0.2045 (3) 0.0441 (9)
C6 0.8089 (4) 0.6237 (4) 0.3073 (3) 0.0449 (9)
H6A 0.855041 0.544152 0.273758 0.054*
H6AB 0.829594 0.692786 0.249438 0.054*
C5 0.6175 (4) 0.6076 (3) 0.3242 (3) 0.0355 (8)
H5 0.576065 0.693593 0.347961 0.043*
C8 0.8441 (4) 0.5697 (3) 0.5310 (3) 0.0351 (8)
C7 0.9012 (4) 0.6552 (4) 0.4258 (3) 0.0417 (9)
H7A 1.021935 0.643993 0.413791 0.050*
H7AB 0.881165 0.745389 0.446456 0.050*
C9 0.6529 (4) 0.5857 (3) 0.5513 (3) 0.0338 (7)
H9 0.622414 0.677940 0.551002 0.041*
C10 0.5819 (4) 0.5177 (3) 0.4360 (3) 0.0336 (7)
C11 0.5965 (4) 0.5222 (4) 0.6700 (3) 0.0420 (9)
H11A 0.480102 0.546565 0.686523 0.050*
H11B 0.600275 0.428615 0.660794 0.050*
C12 0.7069 (4) 0.5615 (4) 0.7772 (3) 0.0440 (9)
H12A 0.664368 0.519595 0.849889 0.053*
H12B 0.698090 0.654564 0.788960 0.053*
C13 0.8931 (4) 0.5255 (3) 0.7605 (3) 0.0412 (8)
C14 0.9573 (4) 0.5852 (3) 0.6417 (3) 0.0416 (8)
H14A 0.975277 0.677280 0.655101 0.050*
H14B 1.066516 0.547096 0.623234 0.050*
C15 1.0019 (5) 0.5633 (4) 0.8717 (3) 0.0563 (10)
H15 0.958460 0.513253 0.940575 0.068*
C16 1.1877 (5) 0.5248 (6) 0.8562 (5) 0.0846 (17)
H16A 1.194572 0.435086 0.833299 0.127*
H16B 1.246856 0.537841 0.931250 0.127*
H16C 1.238324 0.577467 0.794132 0.127*
C17 0.9914 (6) 0.7060 (5) 0.9077 (5) 0.0847 (16)
H17A 1.033624 0.758815 0.842748 0.127*
H17B 1.058302 0.720423 0.979171 0.127*
H17C 0.875658 0.728469 0.923976 0.127*
C18 0.5942 (5) 0.4546 (4) 0.1382 (4) 0.0594 (11)
H18A 0.527554 0.436426 0.067410 0.089*
H18B 0.592320 0.380856 0.191370 0.089*
H18C 0.708762 0.472645 0.114584 0.089*
C19 0.5287 (5) 0.6915 (4) 0.1180 (4) 0.0611 (12)
H19A 0.644044 0.706320 0.094445 0.092*
H19B 0.485736 0.766999 0.158745 0.092*
H19C 0.461467 0.674460 0.047236 0.092*
C20 0.6995 (4) 0.4006 (3) 0.4358 (3) 0.0361 (8)

Source of material

Lophanic acid (100 mg, 0.3125 mmol), triphenylphosphine (PPh3, 164 mg, 0.625 mmol), I2 (40 mg, 0.1562 mmol), K2CO3 (86 mg, 0.625 mmol) were dissolved in methylene chloride (DCM, 2 mL). The resulting mixture was stirred at room temperature for 0.5 h until the starting materials were completely transformed. When the reaction was complete, checked by thin-layer chromatography (TLC) analysis, after termination by pure water (30 mL), the reaction was extracted with methylene chloride (3*90 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (10:1) to afford compound (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H, 6H-8a,4a-(epoxymethano) phenanthren-12-one in 85% yield. And the obtained solid was recrystallized with methanol to obtain the colorless needle crystal.

Experimental details

Comment

Lophanic acid is an abietane diterpenoid compound widely seen in medicinal plants I. flavidus [5] and I. lophanthoides [6]. Studies have revealed that this type of compound has significant antibacterial, anti-inflammatory, antitumor, anti-cancer, and other activities [7], [8], [9], [10], [11], [12]. The research group started from medicinal plants I. flavidus isolated rich in lophanic acid. Nevertheless, the structural modification of the active functional groups and targets of lophanic acid has not been reported in the relevant literature. Hence, to investigate the active site of lophanic acid and synthesize a highly active derivative, we used lophanic acid as a raw material. Under the action of triphenylphosphine/iodine/potassium carbonate, the C8–C9 double bond of corinoic acid was oxidized to a hydroxyl group, where the C-8 hydroxyl group formed a lactone with C-20 carboxylic acid. Finally, the target compound is obtained. The title compound (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano) phenanthren-12-one was obtained by Lophanic acid oxidation, esterification reaction.

The title compound is shown in the figure. The bond lengths and angles which were derived from the title structure are within normal ranges. In the molecule, the carbonyl group was confirmed by the distance d(C20–O1) = 1.210(4) Å. The compound contains three six membered carbon-based rings, one hydroxyl, five methyl and one carbonyl.

Corresponding author: Jiang-Hai Ye, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, P. R. China, E-mail:

Funding source: National Natural Science Foundation of China

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The Technology Fund of Guizhou Administration ofTraditional Chinese Medicine [grant number QZYY-2022-019] and National Natural Science Foundation of China (82204605).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2022-11-27
Accepted: 2023-01-10
Published Online: 2023-02-24
Published in Print: 2023-06-27

© 2022 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
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https://doi.org/10.1515/ncrs-2022-0546
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,Nʹ,Nʺ]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N′1,N′3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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