1,10-Phenanthroline → HCID 11809738, compound

HRID 1581754Notes

Reaction equation

HRID 1581754 reaction equation
[CH3:1][C@@H:2]1[C:7](=[O:8])[CH2:6][C@:5]2([CH:9]([CH3:11])[CH3:10])[C@H:3]1[CH2:4]2.[N:12]1[C:25]2[C:16](=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH:15]=[CH:14][CH:13]=1>>[OH:8][C@@:7]1([C:22]2[CH:21]=[CH:20][C:19]3[C:24](=[C:25]4[C:16](=[CH:17][CH:18]=3)[CH:15]=[CH:14][CH:13]=[N:12]4)[N:23]=2)[C@@H:2]([CH3:1])[C@@H:3]2[C@@:5]([CH:9]([CH3:11])[CH3:10])([CH2:4]2)[CH2:6]1

Participants

3

Reactant 2

HCID 13181,10-PhenanthrolineHCID 12304612HCID 12304612, compound

Product 1

HCID 11809738HCID 11809738, compoundYield 45%

Procedure

By using the general procedure above, (−)-thujone (0.186 g, 1.22 mmol) was reacted with 1,10-phenanthroline to provide 0.083 g (45% yield) of the title compound as a colorless oil: 1H NMR (300 MHz, CDCl3) δ9.16 (dd, J=4.50, 1.80 Hz, Hp9), 8.27 (d, J=8.40 Hz, Hp4), 8.24 (dd, J=8.10, 1.80 Hz, Hp7) 7.82 and 7.76 (two d, J=8.80 Hz, Hp5 and Hp6), 7.72 (d, J=8.40 Hz, Hp3), 7.62 (dd, J=8.10, 4.50 Hz, Hp8), 6.38 (br s, OH), 2.75 (dq, J=6.6, 4.5 Hz, CHCH3), 2.50 (dd, J=13.5, 1.2 Hz, C(OH)CHH), 2.21 (d, J=13.5 Hz, C(OH)CHH), 1.53 (sep, 6.9 Hz, CH(CH3)2), 1.37 (t, J=3.9 Hz, cyclopropyl H), 1.31 (dd, J=4.2, 8.4 Hz, cyclopropyl H), 1.07 (d, J=6.9 Hz, CH3), 0.95 (d, J=6.9 Hz, CH3), 0.89 (d, J=6.9 Hz, CH3), 0.37 (dd, J=4.5, 9.0 Hz, cyclopropyl H); 13C NMR (75 MHz) δ165.09, 150.16, 145.56, 142.86, 137.10, 136.05, 128.98, 127.17, 126.29, 126.05, 122.87, 119.72, 81.85, 48.66, 46.71, 33.01, 32.70, 29.53, 20.10, 19.94, 13.12, 11.60; IR (CHCl3) 3381 (OH), 2957 (C—H Ar), 2928 (CH), 850 (C—H Ar) cm−1; HRMS m/e Calcd for C22H25N2O (MH+): 333.1967, found: 333.1943.

Sources & evidence

ORD record
ord-89241825b3764ee0a2df252b34fade79
Source dataset
uspto-grants-2004_05
Patent number
US06730788B1

Reaction notes

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