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[ CAS No. 1235-74-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1235-74-1
Chemical Structure| 1235-74-1
Structure of 1235-74-1 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1235-74-1 ]

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Product Details of [ 1235-74-1 ]

CAS No. :1235-74-1 MDL No. :MFCD27976778
Formula : C21H30O2 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

Safety of [ 1235-74-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

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 ]

[ 1235-74-1 ] Synthesis Path-Downstream   1~76

  • 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 72% With sodium acetate In acetic anhydride electrooxidation, carbon electrodes;
1: 61% 2: 13% electrooxidation, carbon electrodes;
YieldReaction ConditionsOperation in experiment
Nitrierung;
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 1.) polyphosphoric acid, P2O5, 2.) Tl(NO3)3*H2O / 1.) 40 deg C, 7 h, 2.) CH3OH, THF, RT, 15 min
Multi-step reaction with 6 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 43 percent / polyphosphoric acid, P2O5 / 7 h / 40 °C 6: 80 percent / Tl(NO3)3*H2O / methanol; tetrahydrofuran / 0.25 h / Ambient temperature
  • 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 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 1.) polyphosphoric acid, P2O5, 2.) Tl(NO3)3*H2O / 1.) 40 deg C, 7 h, 2.) CH3OH, 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 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 43 percent / polyphosphoric acid, P2O5 / 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 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 24 percent / polyphosphoric acid, P2O5 / 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 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 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 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 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 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature
  • 21
  • [ 1235-74-1 ]
  • [ 115015-41-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 1.) polyphosphoric acid, P2O5, 2.) Tl(NO3)3*H2O / 1.) 40 deg C, 7 h, 2.) CH3OH, 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*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 43 percent / polyphosphoric acid, P2O5 / 7 h / 40 °C 6: 80 percent / Tl(NO3)3*H2O / 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
  • 22
  • [ 1235-74-1 ]
  • [ 114958-43-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.) DDQ, 2.) Tl(ONO2)3*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 1.) polyphosphoric acid, P2O5, 2.) Tl(NO3)3*H2O / 1.) 40 deg C, 7 h, 2.) CH3OH, 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*H2O / 1.) benzene, reflux, 2.5 h 2.) MeOH, room temp. 30 min. 3: 91 percent / etheral boron trifluoride etherate / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / 2percent alcoholic NaOH / ethanol / 3 h / 50 °C 5: 43 percent / polyphosphoric acid, P2O5 / 7 h / 40 °C 6: 80 percent / Tl(NO3)3*H2O / 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
  • 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
  • C36H39F6NO3 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 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 ]
YieldReaction ConditionsOperation 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
  • 27
  • [ 1235-74-1 ]
  • [ 30905-79-4 ]
  • [ 30885-13-3 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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
  • 30
  • [ 911316-54-6 ]
  • [ 1235-74-1 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
  • C22H31NO3 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
  • C25H37NO3 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
  • C28H35NO3 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
  • C25H36O3 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
  • C28H34O3 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
  • C22H30O3 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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 ]
  • C18H21BrN2O6 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
  • C18H25BrN2O2 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
  • C19H24BrN3O2 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
  • C25H28BrN3O2 [ No CAS ]
YieldReaction ConditionsOperation 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 ]
  • C21H29BrO2 [ No CAS ]
YieldReaction ConditionsOperation 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%
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