Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone

Table 3

DFT-calculated ¹³C NMR chemical shifts (ppm) for compounds 2, 3, 6, 8, 11, and 12.

Compound	C-1	C-2	C-3	C-4	C-4a	C-5	C-6	C-7	C-8	C-8a	CH3
2-Hydroxy juglone (2)	181.93	156.99	107.41	190.08	112.87	163.49	127.36	133.75	118.07	129.19	—
3-Hydroxy juglone (11)	181.77	108.35	156.87	185.51	111.33	163.53	121.69	138.31	118.51	132.99	—
2-Hydroxy-7-methyl juglone (3)	182.16	156.97	107.50	189.51	110.56	163.81	126.85	147.59	118.88	128.95	19.63
3-Hydroxy-7-methyl juglone (8)	182.07	108.00	157.30	184.36	109.37	163.93	121.10	152.92	119.59	133.35	20.78
2-Methoxy juglone (12)	178.88	162.04	106.98	189.90	112.93	163.45	124.69	134.41	117.97	131.52	51.86
3-Methoxy juglone (6)	181.91	107.32	161.80	184.56	112.91	163.95	122.57	136.40	117.42	131.94	51.74
6, observed (this work)	183.95	110.50	160.08	184.94	114.28	161.98	123.87	137.20	118.95	132.06	56.61