Alternatived Products of [ 1235-74-1 ]
Product Details of [ 1235-74-1 ]
CAS No. : 1235-74-1
MDL No. : MFCD27976778
Formula :
C21 H30 O2
Boiling Point :
-
Linear Structure Formula : -
InChI Key : PGZCJOPTDHWYES-HMXCVIKNSA-N
M.W :
314.46
Pubchem ID : 14697
Synonyms :
Calculated chemistry of [ 1235-74-1 ]
Physicochemical Properties
Num. heavy atoms :
23
Num. arom. heavy atoms :
6
Fraction Csp3 :
0.67
Num. rotatable bonds :
3
Num. H-bond acceptors :
2.0
Num. H-bond donors :
0.0
Molar Refractivity :
95.7
TPSA :
26.3 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
Yes
P-gp substrate :
No
CYP1A2 inhibitor :
No
CYP2C19 inhibitor :
Yes
CYP2C9 inhibitor :
Yes
CYP2D6 inhibitor :
Yes
CYP3A4 inhibitor :
No
Log Kp (skin permeation) :
-4.58 cm/s
Lipophilicity
Log Po/w (iLOGP) :
3.86
Log Po/w (XLOGP3) :
5.13
Log Po/w (WLOGP) :
4.99
Log Po/w (MLOGP) :
4.67
Log Po/w (SILICOS-IT) :
5.45
Consensus Log Po/w :
4.82
Druglikeness
Lipinski :
1.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
1.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-5.02
Solubility :
0.00303 mg/ml ; 0.00000962 mol/l
Class :
Moderately soluble
Log S (Ali) :
-5.43
Solubility :
0.00118 mg/ml ; 0.00000374 mol/l
Class :
Moderately soluble
Log S (SILICOS-IT) :
-6.02
Solubility :
0.000302 mg/ml ; 0.000000959 mol/l
Class :
Poorly soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
3.6
Application In Synthesis of [ 1235-74-1 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Downstream synthetic route of [ 1235-74-1 ]
1
[ 67-56-1 ]
[ 1235-74-1 ]
7-keto dehydroabietic acid methyl ester
[ No CAS ]
(1R,4aS)-7-(1-Methoxy-1-methyl-ethyl)-1,4a-dimethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 52%
2: 27%
With lithium perchlorate electrooxidation;
2
[ 67-56-1 ]
[ 1235-74-1 ]
methyl 1,2,3,4,4a,9,10,10a-octahydro-9-methoxy-1, 4a-dimethyl-7-(1-methylethyl)1-phenantrenecarboxylate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
79%
With lithium perchlorate electrooxidation, carbon electrodes;
3
abietic acid methyl ester
[ No CAS ]
[ 1235-74-1 ]
7-keto dehydroabietic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With 3-chloro-benzenecarboperoxoic acid In chloroform for 3h; Heating; Yield given;
4
abietic acid methyl ester
[ No CAS ]
[ 1235-74-1 ]
7-keto dehydroabietic acid methyl ester
[ No CAS ]
[ 89288-45-9 ]
Yield Reaction Conditions Operation in experiment
With mercury(II) diacetate; ozone; acetaldehyde 1.) -78 deg C, methanol, 30 min; Yield given. Multistep reaction;
5
abietic acid methyl ester
[ No CAS ]
[ 1235-74-1 ]
[ 13082-81-0 ]
(1R,4aS,9S)-9-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester
[ No CAS ]
(1R,4aS,9R)-9-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 75 mg
2: 45 mg
With selenium(IV) oxide In <i>tert</i>-butyl alcohol for 24h; Ambient temperature;
6
[ 1235-74-1 ]
[ 22465-60-7 ]
Yield Reaction Conditions Operation in experiment
45%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 2.5h; Heating;
7
[ 1235-74-1 ]
7-keto dehydroabietic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
72%
With sodium acetate In acetic anhydride; acetic acid electrooxidation;
8
[ 1235-74-1 ]
7-keto dehydroabietic acid methyl ester
[ No CAS ]
[ 60188-95-6 ]
Yield Reaction Conditions Operation in experiment
1: 6%
2: 52%
With hydrogenchloride; ruthenium(IV) oxide; sodium dihydrogenphosphate; sodium chloride In tetrachloromethane; water electrooxidation, platinum electrodes;
9
[ 1235-74-1 ]
[ 53655-52-0 ]
Yield Reaction Conditions Operation in experiment
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; thallium(III) nitrate 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.; Yield given. Multistep reaction;
10
[ 1235-74-1 ]
[ 52525-66-3 ]
Yield Reaction Conditions Operation in experiment
25%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 70 - 75℃; for 12h;
11
[ 1235-74-1 ]
[ 64-19-7 ]
(1R,4aS)-9-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester
[ No CAS ]
7-acetoxydehydroabietic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 3%
2: 72%
With sodium acetate In acetic anhydride electrooxidation, carbon electrodes;
1: 61%
2: 13%
electrooxidation, carbon electrodes;
Reference:
[1]Uneyama, Kenji; Katayama, Tatsuo; Torii, Sigeru
[Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 3043 - 3044]
[2]Uneyama, Kenji; Katayama, Tatsuo; Torii, Sigeru
[Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 3043 - 3044]
Yield Reaction Conditions Operation in experiment
Nitrierung;
Yield Reaction Conditions Operation in experiment
Levopimarsaeure, 1.) KOH, 2.) CH2N2 (neben anderen);
Methyllevopimarat, KOH bzw. Tris-n-butylamin (neben anderen);
durch Birch-Reduktion von 3a;
d.Triazolidionaddukt V durch basische Hydrolyse;
Dioxanverb. IIb, HI;
14
[ 1235-74-1 ]
4α-carbometoxy-4β-methyl-18-nor-5α-pregna-8,11,13-triene-15,20-dione
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 1.) polyphosphoric acid, P2 O5 , 2.) Tl(NO3 )3*H2 O / 1.) 40 deg C, 7 h, 2.) CH3 OH, THF, RT, 15 min
Multi-step reaction with 6 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 43 percent / polyphosphoric acid, P2 O5 / 7 h / 40 °C
6: 80 percent / Tl(NO3 )3*H2 O / methanol; tetrahydrofuran / 0.25 h / Ambient temperature
Reference:
[1]Abad, A.; Agullo, C.; Arno, M.; Domingo, L.R.; Zaragoza, R.J.
[Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3761 - 3765]
[2]Abad, A.; Agullo, C.; Arno, M.; Domingo, L.R.; Zaragoza, R.J.
[Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3761 - 3765]
15
[ 1235-74-1 ]
(4R,11bS)-8-Acetyl-4,11b-dimethyl-10-oxo-2,3,4,4a,5,6,8,9,10,11b-decahydro-1H-cyclopenta[b]phenanthrene-4-carboxylic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 1.) polyphosphoric acid, P2 O5 , 2.) Tl(NO3 )3*H2 O / 1.) 40 deg C, 7 h, 2.) CH3 OH, THF, RT, 15 min
16
[ 1235-74-1 ]
4α-carbomethoxy-20,20-(ethylenedithio)-4β-methyl-18-nor-5α-pregna-18,11,13-trien-15-one
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 43 percent / polyphosphoric acid, P2 O5 / 7 h / 40 °C
17
[ 1235-74-1 ]
(4R,4aR,11bS)-4,11b-Dimethyl-8-(2-methyl-[1,3]dithiolan-2-yl)-10-oxo-2,3,4,4a,5,6,8,9,10,11b-decahydro-1H-cyclopenta[b]phenanthrene-4-carboxylic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 24 percent / polyphosphoric acid, P2 O5 / 7 h / 40 °C
18
[ 1235-74-1 ]
methyl 13-<1'-((methoxycarbonyl)methyl)-2'-oxo-propyl>podocarpa-8,11,13-trien-18-oate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
19
[ 1235-74-1 ]
methyl 13-<1'-(carboxymethyl)-2',2'-(ethylenedithio)-propyl>podocarpa-8,11,13-trien-18-oate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
20
[ 1235-74-1 ]
methyl 13-<1'-((methoxycarbonyl)methyl)-2',2'-(ethylenedithio)propyl>podocarpa-8,11,13-trien-18-oate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
21
[ 1235-74-1 ]
[ 115015-41-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 1.) polyphosphoric acid, P2 O5 , 2.) Tl(NO3 )3*H2 O / 1.) 40 deg C, 7 h, 2.) CH3 OH, THF, RT, 15 min
6: 1.) H2 , 2.) Jones reagent / 1.) 10percent Pd/C / 1.) acetic acid, RT, overnight, 2.) acetone, 0 deg C
Multi-step reaction with 7 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 43 percent / polyphosphoric acid, P2 O5 / 7 h / 40 °C
6: 80 percent / Tl(NO3 )3*H2 O / methanol; tetrahydrofuran / 0.25 h / Ambient temperature
7: 1.) H2 , 2.) Jones reagent / 1.) 10percent Pd/C / 1.) acetic acid, RT, overnight, 2.) acetone, 0 deg C
Reference:
[1]Abad, A.; Agullo, C.; Arno, M.; Domingo, L.R.; Zaragoza, R.J.
[Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3761 - 3765]
[2]Abad, A.; Agullo, C.; Arno, M.; Domingo, L.R.; Zaragoza, R.J.
[Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3761 - 3765]
22
[ 1235-74-1 ]
[ 114958-43-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 1.) polyphosphoric acid, P2 O5 , 2.) Tl(NO3 )3*H2 O / 1.) 40 deg C, 7 h, 2.) CH3 OH, THF, RT, 15 min
6: 1.) H2 , 2.) Jones reagent / 1.) 10percent Pd/C / 1.) acetic acid, RT, overnight, 2.) acetone, 0 deg C
Multi-step reaction with 7 steps
1: 1.) DDQ, 2.) Tl(ONO2 )3*H2 O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min.
3: 91 percent / etheral boron trifluoride etherate / CH2 Cl2 / 24 h / Ambient temperature
4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C
5: 43 percent / polyphosphoric acid, P2 O5 / 7 h / 40 °C
6: 80 percent / Tl(NO3 )3*H2 O / methanol; tetrahydrofuran / 0.25 h / Ambient temperature
7: 1.) H2 , 2.) Jones reagent / 1.) 10percent Pd/C / 1.) acetic acid, RT, overnight, 2.) acetone, 0 deg C
Reference:
[1]Abad, A.; Agullo, C.; Arno, M.; Domingo, L.R.; Zaragoza, R.J.
[Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3761 - 3765]
[2]Abad, A.; Agullo, C.; Arno, M.; Domingo, L.R.; Zaragoza, R.J.
[Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3761 - 3765]
23
[ 1235-74-1 ]
methyl (3aS,4R,9aR,10R,13aS,13dR)-4-(3-chlorophenyl)-6-isopropyl10,13a-dimethyl-3a,4,5,8,9,9a,10,11,12,13,13a,13d-dodecahydro-3H-cyclopenta[c]naphtho[1,2f]-quinoline-10-carboxylate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: potassium nitrate; trifluoroacetic acid / acetic anhydride / 1 h / -10 °C
1.2: 20 °C
2.1: trifluoroacetic acid / acetonitrile / 6 h / 20 °C
24
[ 1235-74-1 ]
methyl (3aS,4R,9aR,10R,13aS,13dR)-4-(2-fluorophenyl)-6-isopropyl-10,13a-dimethyl-3a,4,5,8,9,9a,10,11,12,13,13a,13d-dodecahydro-3H-cyclopenta[c]naphtho[1,2f]-quinoline-10-carboxylate
[ No CAS ]
methyl (3aS,4S,9aR,10R,13aS,13dR)-4-(2-fluorophenyl)-6-isopropyl-10,13a-dimethyl-3a,4,5,8,9,9a,10,11,12,13,13a,13d-dodecahydro-3H-cyclopenta[c]naphtho[1,2f]-quinoline-10-carboxylate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: potassium nitrate; trifluoroacetic acid / acetic anhydride / 1 h / -10 °C
1.2: 20 °C
2.1: trifluoroacetic acid / acetonitrile / 20 h / 20 °C
25
[ 1235-74-1 ]
C36 H39 F6 NO3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: potassium nitrate; trifluoroacetic acid / acetic anhydride / 1 h / -10 °C
1.2: 20 °C
2.1: trifluoroacetic acid / acetonitrile / 4 h / 20 °C
3.1: triethylamine; dmap / benzene / 26 h / 20 °C
Multi-step reaction with 3 steps
1.1: potassium nitrate; trifluoroacetic acid / acetic anhydride / 1 h / -10 °C
1.2: 20 °C
2.1: trifluoroacetic acid / acetonitrile / 4 h / 20 °C
3.1: triethylamine; dmap / benzene / 26 h / 20 °C
Reference:
[1]Tolstikov; Savchenko; Lukina; Nedopekin; Odinokov
[Russian Chemical Bulletin, 2013, vol. 62, # 1, p. 203 - 211][Izv. Akad. Nauk, Ser. Khim., 2013, p. 203 - 210]
[2]Tolstikov; Savchenko; Lukina; Nedopekin; Odinokov
[Russian Chemical Bulletin, 2013, vol. 62, # 1, p. 203 - 211][Izv. Akad. Nauk, Ser. Khim., 2013, p. 203 - 210]
26
[ 1235-74-1 ]
methyl (1S,4R,5aS,6R,11aR,12R,15aS,15dR)-8-isopropyl-12,15a-dimethyl-7-trifluoroacetyl-6-(4-trifluoromethylphenyl)-4,5,5a,6,7,10,11,11a,12,13,14,15,15a,15d-tetradecahydro-1H-1,4-epoxy[1,2]dioxepino[5,4c]naphtho[1,2-f]quinoline-12-carboxylate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: potassium nitrate; trifluoroacetic acid / acetic anhydride / 1 h / -10 °C
1.2: 20 °C
2.1: trifluoroacetic acid / acetonitrile / 4 h / 20 °C
3.1: triethylamine; dmap / benzene / 26 h / 20 °C
4.1: ozone / dichloromethane / 0.05 h / 0 °C
Multi-step reaction with 4 steps
1.1: potassium nitrate; trifluoroacetic acid / acetic anhydride / 1 h / -10 °C
1.2: 20 °C
2.1: trifluoroacetic acid / acetonitrile / 4 h / 20 °C
3.1: triethylamine; dmap / benzene / 26 h / 20 °C
4.1: ozone / dichloromethane / 0.05 h / 0 °C
Reference:
[1]Tolstikov; Savchenko; Lukina; Nedopekin; Odinokov
[Russian Chemical Bulletin, 2013, vol. 62, # 1, p. 203 - 211][Izv. Akad. Nauk, Ser. Khim., 2013, p. 203 - 210]
[2]Tolstikov; Savchenko; Lukina; Nedopekin; Odinokov
[Russian Chemical Bulletin, 2013, vol. 62, # 1, p. 203 - 211][Izv. Akad. Nauk, Ser. Khim., 2013, p. 203 - 210]
27
[ 1235-74-1 ]
[ 30905-79-4 ]
[ 30885-13-3 ]
Yield Reaction Conditions Operation in experiment
With potassium nitrate; trifluoroacetic acid In acetic anhydride at -10℃; for 1h; Overall yield = 86 %; Overall yield = 0.27 g;
28
[ 1235-74-1 ]
methyl 12-aminodehydroabietate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
35%
Stage #1: methyl dehydroabietate With potassium nitrate; trifluoroacetic acid In acetic anhydride at -10℃; for 1h;
Stage #2: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol at 20℃;
29
[ 1235-74-1 ]
methyl (3aS,4R,9aR,10R,13aS,13dR)-6-isopropyl-10,13a-dimethyl-4(4-trifluoromethylphenyl)3a,4,5,8,9,9a,10,11,12,13,13a,13d-dodecahydro3Hcyclopenta[c]naphtho[1,2f]quinoline-10-carboxylate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: potassium nitrate; trifluoroacetic acid / acetic anhydride / 1 h / -10 °C
1.2: 20 °C
2.1: trifluoroacetic acid / acetonitrile / 4 h / 20 °C
Multi-step reaction with 2 steps
1.1: potassium nitrate; trifluoroacetic acid / acetic anhydride / 1 h / -10 °C
1.2: 20 °C
2.1: trifluoroacetic acid / acetonitrile / 4 h / 20 °C
Reference:
[1]Tolstikov; Savchenko; Lukina; Nedopekin; Odinokov
[Russian Chemical Bulletin, 2013, vol. 62, # 1, p. 203 - 211][Izv. Akad. Nauk, Ser. Khim., 2013, p. 203 - 210]
[2]Tolstikov; Savchenko; Lukina; Nedopekin; Odinokov
[Russian Chemical Bulletin, 2013, vol. 62, # 1, p. 203 - 211][Izv. Akad. Nauk, Ser. Khim., 2013, p. 203 - 210]
30
[ 911316-54-6 ]
[ 1235-74-1 ]
Yield Reaction Conditions Operation in experiment
90.4%
With sulfuric acid In methanol at 90℃; for 12h;
1.A
A. The compound (DHAA) (10.5 g, 0.035 mol) was dissolved in methanol (280 mL)Slowly dropwise concentrated H2SO4 (24 mL),More than ten minutes,90 oil bath for about 12 hours of continuous stirring,Separation and purification of 9.9 g colorless transparent crystals,Namely compound (W-1),Yield 90.4%;
31
[ 1235-74-1 ]
[ 75-36-5 ]
methyl 12-acetyldehydroabietate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
99%
With aluminum oxide In tetrachloromethane at -10 - 20℃; for 12h; Inert atmosphere;
18.B
B. Under a nitrogen atmosphere,Aluminum trioxide (488 mg, 3.66 mmol) was dissolved in carbon tetrachloride (4 mL)Under ice-salt bath,Acetyl chloride (0.17 mL, 2.38 mmol) was added dropwise,The compound (W-1) (500 mg, 1.59 mmol) was dissolved in carbon tetrachloride (4 mL)Stirring slowly into the reaction system,While maintaining the temperature drop below -10 during the dropwise addition,After maintaining the low temperature for 2 hours,Transfer to room temperature for 10 hours,After the post-treatment, 524 mg of yellowish powder was isolated and purified,I.e., the compound (W-6a),Yield 99.0%;
32
[ 1235-74-1 ]
C22 H31 NO3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
33
[ 1235-74-1 ]
(1R,4aS)-6-((E)-(hydroxyimino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
34
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-6-((E)-(methoxyimino)methyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
35
[ 1235-74-1 ]
(1R,4aS)-6-((E)-(ethoxyimino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
36
[ 1235-74-1 ]
(1R,4aS)-6-((E)-(isopropoxyimino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
37
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-((octyloxy)imino)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
38
[ 1235-74-1 ]
(1R,4aS)-6-((E)-((cyclopropylmethoxy)imino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
39
[ 1235-74-1 ]
(1R,4aS)-6-((E)-((cyclohexyloxy)imino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
40
[ 1235-74-1 ]
(1R,4aS)-6-((E)-((allyloxy)imino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
41
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-(((3-methylbut-2-en-1-yl)oxy)imino)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
42
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-((prop-2-yn-1-yloxy)imino)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
43
[ 1235-74-1 ]
(1R,4aS)-6-((E)-((benzyloxy)imino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
44
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-(((4-methylbenzyl)oxy)imino)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
45
[ 1235-74-1 ]
(1R,4aS)-6-((E)-(((4-fluorobenzyl)oxy)imino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
46
[ 1235-74-1 ]
(1R,4aS)-6-((E)-(((4-bromobenzyl)oxy)imino)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
47
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-(((4-(trifluoromethoxy)benzyl)oxy)imino)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
48
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-((naphthalen-1-ylmethoxy)imino)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
49
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-((naphthalen-2-ylmethoxy)imino)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / nitrobenzene / 10 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
50
[ 1235-74-1 ]
(1R,4aS)-methyl-6-(1-(hydroxyimino)ethyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
51
[ 1235-74-1 ]
(1R,4aS)-6-((E)-1-(hydroxyimino)ethyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
52
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-6-((E)-1-(methoxyimino)ethyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
53
[ 1235-74-1 ]
(1R,4aS)-6-((E)-1-((allyloxy)imino)ethyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
54
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-1-((prop-2-yn-1-yloxy)imino)ethyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
55
[ 1235-74-1 ]
(1R,4aS)-6-((E)-1-((benzyloxy)imino)ethyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
56
[ 1235-74-1 ]
C25 H37 NO3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
57
[ 1235-74-1 ]
(1R,4aS)-6-((E)-1-(hydroxyimino)-2-methylpropyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
58
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-6-((E)-1-(methoxyimino)-2-methylpropyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
59
[ 1235-74-1 ]
(1R,4aS)-6-((E)-1-((allyloxy)imino)-2-methylpropyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
60
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-2-methyl-1-((prop-2-yn-1-yloxy)imino)propyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
61
[ 1235-74-1 ]
(1R,4aS)-6-((E)-1-((benzyloxy)imino)-2-methylpropyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
62
[ 1235-74-1 ]
C28 H35 NO3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
63
[ 1235-74-1 ]
(1R,4aS)-6-((E)-(hydroxyimino)(phenyl)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
64
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-6-((E)-(methoxyimino)(phenyl)methyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
65
[ 1235-74-1 ]
(1R,4aS)-6-((E)-((allyloxy)imino)(phenyl)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
66
[ 1235-74-1 ]
(1R,4aS)-7-isopropyl-1,4a-dimethyl-6-((E)-phenyl((prop-2-yn-1-yloxy)imino)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
67
[ 1235-74-1 ]
(1R,4aS)-6-((E)-((benzyloxy)imino)(phenyl)methyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere
2: hydroxylamine hydrochloride; pyridine / ethanol / 90 °C
3: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 20 °C
4: potassium hydroxide / ethanol / 80 °C
68
[ 1235-74-1 ]
[ 79-30-1 ]
C25 H36 O3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
87.2%
With aluminum oxide In tetrachloromethane at -10 - 20℃; for 12h; Inert atmosphere;
23.B
B. Under a nitrogen atmosphere, Aluminum trioxide (488 mg, 3.66 mmol) was dissolved in carbon tetrachloride (4 mL)Under ice-salt bath,Isobutyryl chloride (0.63 mL, 2.38 mmol) was added dropwise,The compound (W-1) (500 mg, 1.59 mmol) was dissolved in carbon tetrachloride (4 mL)Stirring slowly into the reaction system,While maintaining the temperature drop below -10 during the dropwise addition,After maintaining the low temperature for 2 hours,Transfer to room temperature for 10 hours,After the post-treatment, 645 mg of the yellowish powder was isolated and purified,I.e., the compound (W-6b),Yield 87.2%;
69
[ 1235-74-1 ]
[ 98-88-4 ]
C28 H34 O3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
85.5%
With aluminum oxide In tetrachloromethane at -10 - 20℃; for 12h; Inert atmosphere;
28.B
B. Under a nitrogen atmosphere,Aluminum trioxide (488 mg, 3.66 mmol) was dissolved in carbon tetrachloride (4 mL)Under ice-salt bath,Benzoyl chloride (0.55 mL, 2.38 mmol) was added dropwise,The compound (W-1) (500 mg, 1.59 mmol) was dissolved in carbon tetrachloride (4 mL)Stirring slowly into the reaction system,While maintaining the temperature drop below -10 during the dropwise addition,After maintaining the low temperature for 2 hours,Transfer to room temperature for 10 hours,After the post-treatment, 645 mg of the yellowish powder was isolated and purified,I.e., the compound (W-6c),Yield 85.5%;
70
[ 4885-02-3 ]
[ 1235-74-1 ]
C22 H30 O3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
55.8%
With aluminum (III) chloride In nitrobenzene at 20℃; for 10h;
1.B
B. The compound (W-1) (500 mg, 1.59 mmol) was dissolved in nitrobenzene (8 mL)Aluminum chloride (1.1 g, 8.25 mmol) was added successively with stirring,Dichloromethyl methyl ether (0.19 mL, 2.07 mmol)Stirred at room temperature for 10 hours,After the post-treatment separation and purification of 304 mg yellowish powder,I.e., the compound (W-2),Yield 55.8%;
71
[ 67-56-1 ]
[ 911316-54-6 ]
[ 1235-74-1 ]
Yield Reaction Conditions Operation in experiment
97.6%
Stage #1: dehydroabietic acid With thionyl chloride In benzene for 3h; Reflux;
Stage #2: methanol for 3h; Reflux;
1 Synthesis of Methyl Dehydroabietate (III)
In a 500 mL three-neck round bottom flask,30 g (0.1 mol) of dehydroabietic acid was dissolved in 100 mL of benzene.Slowly add 10.9 mL of thionyl chloride (0.15 mol) and heat to reflux for 3 h.After the reaction,The benzene and excess thionyl chloride in the reaction solution were removed under reduced pressure.A dehydroabietic acid chloride was obtained as a yellow oil.Add 60 mL of methanol to the bottle.Heated back to reflux for 3 h,After the reaction,The solvent was removed under reduced pressure.Recrystallization of ethanol to obtain white needle crystal is dehydroabietic acid methyl ester(30.63g, 97.6%),
72
[ 1235-74-1 ]
C18 H21 BrN2 O6
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C / Darkness
2: nitric acid; sulfuric acid / 0.67 h / Cooling with ice
73
[ 1235-74-1 ]
C18 H25 BrN2 O2
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C / Darkness
2: nitric acid; sulfuric acid / 0.67 h / Cooling with ice
3: iron; hydrogenchloride / ethanol; water / 1.5 h / Reflux
74
[ 1235-74-1 ]
C19 H24 BrN3 O2
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C / Darkness
2: nitric acid; sulfuric acid / 0.67 h / Cooling with ice
3: iron; hydrogenchloride / ethanol; water / 1.5 h / Reflux
4: ethanol; water / 5 h / Reflux
75
[ 1235-74-1 ]
C25 H28 BrN3 O2
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C / Darkness
2.1: nitric acid; sulfuric acid / 0.67 h / Cooling with ice
3.1: iron; hydrogenchloride / ethanol; water / 1.5 h / Reflux
4.1: ethanol; water / 5 h / Reflux
5.1: tris-(dibenzylideneacetone)dipalladium(0) / <i>tert</i>-butyl alcohol / 0.05 h / 85 °C
5.2: 24 h / 120 °C / Reflux
76
[ 1235-74-1 ]
C21 H29 BrO2
[ No CAS ]
Yield Reaction Conditions Operation in experiment
67%
With N-Bromosuccinimide In acetonitrile at 20℃; for 24h; Darkness;
2 Synthesis of 12-Bromodehydroabietic Acid Methyl Ester (IV)
15 g of dehydroabietic acid methyl ester was dissolved in 100 mL of dry acetonitrile, and then 12 g of NBS was added to the mixed solution.At room temperature,After 24 hours in the dark, the solvent acetonitrile was distilled off under reduced pressure.And add methylene chloride while hot, after cooling,The insoluble matter in the solution was filtered off, the solvent was evaporated under reduced pressure, and dissolved in anhydrous methanol.Recrystallization gave 10.5 g of white needle crystals.Is 12-bromo dehydroabietic acid methyl ester,Yield 67%