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Dimethylformamide → Anthrone

HRID 462936
Notes
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Reaction equation

HRID 462936 reaction equation
CC1C=CC2O[C:44](=O)[C:13]3=C(O)[C:15]4[C:16](=[C:17](O[C@@H]5O[C@H](C)[C@H](O)[C@H](O)[C@H]5O[C@H]5O[C@H](C)[C@H](O)[C@H](OC)[C@H]5O)[CH:18]=[CH:19][CH:20]=4)[C:11]4=[C:12]3[C:6]=2[C:7]=1[C:8](O4)=O.[CH3:47][C:48]1[CH:49]=[CH:50][C:51]2[O:93][C:91](=[O:92])[C:59]3=[C:60]([OH:90])[C:61]4[C:62](=[C:63]([O:67][C@@H:68]5[O:73][C@H:72]([CH3:74])[C@H:71]([OH:75])[C@@:70]([OH:77])([CH3:76])[C@H:69]5[O:78][C@H:79]5[O:84][C@H:83]([CH3:85])[C@H:82]([OH:86])[C@H:81]([O:87][CH3:88])[C@H:80]5[NH2:89])[CH:64]=[CH:65][CH:66]=4)[C:57]4=[C:58]3[C:52]=2[C:53]=1[C:54]([O:56]4)=[O:55].CN(C)[CH:96]=[O:97].O1CCOCC1>CS(C)=O.CO.O.C(Cl)(Cl)Cl.C(O)C>[CH3:47][C:48]1[CH:49]=[CH:50][C:51]2[O:93][C:91](=[O:92])[C:59]3=[C:60]([OH:90])[C:61]4[C:62](=[C:63]([O:67][C@@H:68]5[O:73][C@H:72]([CH3:74])[C@H:71]([OH:75])[C@@:70]([OH:77])([CH3:76])[C@H:69]5[O:78][C@H:79]5[O:84][C@H:83]([CH3:85])[C@H:82]([OH:86])[C@H:81]([O:87][CH3:88])[C@H:80]5[NH2:89])[CH:64]=[CH:65][CH:66]=4)[C:57]4=[C:58]3[C:52]=2[C:53]=1[C:54]([O:56]4)=[O:55].[CH:7]1[C:6]2[C:96](=[O:97])[C:15]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11][C:12]=2[CH:13]=[CH:44][CH:8]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

11

Reactant 4

HCID 6228DimethylformamideHCID 312751,4-DioxaneHCID 5281394ChartreusinHCID 5362259Elsamitrucin2×

Product 2

HCID 7018AnthroneHCID 5362259Elsamitrucin

Reagents, catalysts & solvents 5

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

BBM-2478 A and B were obtained as yellowish-orange crystalline solids. Both components of BBM-2478 are distinguishable from chartreusin by thin layer chromatography (TLC) as shown in Table 5. BBM-2478A is readily soluble in dimethyl sulfoxide, dimethylformamide, dioxane and acidic water, slightly soluble in methanol, ethanol and chloroform and insoluble in other organic solvents. Solubility of BBM-2478B is similar to that of BBM-2478A except that BBM-2478B is insoluble in acidic water. BBM-2478 A and B give positive responses with ferric chloride and anthrone reagents. BBM-2478A shows positive reaction to ninhydrin, while BBM-2478B is negative in the same test. Tollen's and Sakaguchi reactions are negative with both components. The physico-chemical properties of BBM-2478A and B are summarized in Table 6. The UV spectra of the two components are similar, showing maxima at 236, 266, 398 and 422 nm in neutral and acidic solutions and at 240, 268 and 435 nm in alkaline solution. These spectra are closely related to that of chartreusin. The IR spectra of BBM-2478 A and B are illustrated in FIGS. 1 and 2, respectively. The proton (PMR) and 13C-NMR (CMR) spectra of BBM-2478A are shown in FIGS. 3 and 4.

Sources & evidence

ORD record
ord-645c37a852a14fc88cc2b0e65d7b4f2d
Source dataset
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04518589

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes