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[ CAS No. 10293-06-8 ] {[proInfo.proName]}

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Chemical Structure| 10293-06-8
Chemical Structure| 10293-06-8
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Product Details of [ 10293-06-8 ]

CAS No. :10293-06-8 MDL No. :MFCD00003744
Formula : C10H15BrO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 231.13 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 10293-06-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.51
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.9
Log Po/w (WLOGP) : 2.78
Log Po/w (MLOGP) : 2.74
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.184 mg/ml ; 0.000794 mol/l
Class : Soluble
Log S (Ali) : -2.92
Solubility : 0.279 mg/ml ; 0.00121 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.25
Solubility : 0.131 mg/ml ; 0.000569 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.61

Safety of [ 10293-06-8 ]

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

Application In Synthesis of [ 10293-06-8 ]

* 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 [ 10293-06-8 ]

[ 10293-06-8 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 10293-06-8 ]
  • [ 10293-10-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; bromine
With chlorosulphuric acid; bromine at 25 - 30℃;
With chlorosulfonic acid; bromine for 5h;
With bromine In chlorosulfonic acid for 1h; first in an ice bath then without it; Yield given;

  • 2
  • [ 10293-06-8 ]
  • [ 1217497-39-6 ]
YieldReaction ConditionsOperation in experiment
72% With chlorosulfonic acid; bromine 1.) ice bath, 5 min, 2.) r.t., 1.5 h;
With chlorosulfonic acid; bromine
  • 3
  • [ 464-49-3 ]
  • [ 10293-06-8 ]
YieldReaction ConditionsOperation in experiment
82% With bromine; acetic acid at 20 - 90℃; (1R, 3S, 4S)-3-Bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 114 Acetic acid (50 mL) was added to (+)-camphor 10 (20 g, 131 mmol) in a 3-neck flask. The solution was heated under reflux at 80-90 oC and a solution of bromine (8 mL, 155 mmol) in acetic acid (8 mL) was added slowly in small aliquots to prevent the deep red colour of excess bromine building up. The solution was heated under reflux at 80-90 oC for a further 2 h and then allowed to cool to room temperature and stirred overnight. The mixture was then added dropwise with stirring to ice/water (120 mL). The resulting precipitate was filtered off and washed with 20 mL portions of water until the filtrate was colourless. The solid was sucked dry on the Buchner funnel and left to dry in the air for a day. The solid was then taken up in ether, dried, filtered and concentrated under reduced pressure to afford the title compound as a white solid (24.85 g, 82 %). m.p.: 75 oC (from ether); Lit.5: 76 oC. [α]D (c 1.01, MeOH, 22 oC) +125.7; Lit.5: (c 1.0, 23 oC) +125. IR: max (N) 2921, 1761 (C=O), 1459, 1375, 1318, 1274, 1208, 1105, 1034, 1003, 911, 808, 767, 691 cm-1. 1H NMR (400.1 MHz; CDCl3; Me4Si): 0.95 (3H, s, 1-CH3), 0.99 (3H, s, 7-CH3), 1.09 (3H, s, 7-CH3), 1.41-1.48 (1H, m), 1.65-1.74 (1H, m), 1.85-1.94 (1H, m), 2.07-2.13 (1H, m), 2.32 (1H, t, 3J = 4.7, 4-CH), 4.64 (1H, d, 3J = 4.7, 3-CH exo) ppm. 13C NMR (100.6 MHz; CDCl3; Me4Si): δ 9.1 (1-CH3), 19.4 (7-CH3), 19.5 (7-CH3), 21.9 (C-5), 30.0 (C-6), 45.4 (C-7), 49.1 (C-4), 53.4 (C-3), 57.1 (C-1), 212.1 (C-2) ppm. HRMS (CI) m/z 253.0213: calculated for [C10H15OBr + Na]+ 253.0203.
69% With bromine; acetic acid at 80℃; for 6h;
50% With bromine In chlorosulfonic acid for 1h;
With aluminium trichloride; bromine
With bromine
With bromine; acetic acid

  • 4
  • [ 10293-06-8 ]
  • [ 464-49-3 ]
YieldReaction ConditionsOperation in experiment
95% With tri-n-butyl-tin hydride; silica gel In dichloromethane for 24h; Ambient temperature;
81% With phenylsilane; sodium hydrogencarbonate In tetrahydrofuran for 1.5h; Heating;
75% With rongalite In N,N-dimethyl-formamide at 100℃; for 36h;
With zinc In ethanol for 16h; Heating;

  • 6
  • [ 10293-06-8 ]
  • [ 85719-15-9 ]
YieldReaction ConditionsOperation in experiment
63% With chlorosulfonic acid; bromine at 25℃; for 5h;
  • 7
  • [ 10293-06-8 ]
  • [ 10334-26-6 ]
YieldReaction ConditionsOperation in experiment
With air; sodium iodide In dimethyl sulfoxide at 150℃; for 6h;
  • 8
  • [ 10293-06-8 ]
  • ammonium (1R,3S,4S,7R)-(3-bromo-1,7-dimethyl-2-oxobicyclo[2.2.1]hept-7-yl)methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With chlorosulfonic acid; ammonium carbonate
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 3 h / 50 °C 2: ammonium hydroxide / water / 20 °C
  • 9
  • [ 375-16-6 ]
  • [ 10293-06-8 ]
  • 3-(perfluorobutyryl)-(+)camphor [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With samarium diiodide In tetrahydrofuran at 0℃; for 2h;
  • 10
  • [ 40079-92-3 ]
  • [ 10293-06-8 ]
  • (1R,3S,4R)-3-(Adamantane-2-carbonyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With samarium diiodide In tetrahydrofuran at 0℃; for 3h;
  • 11
  • [ 16331-52-5 ]
  • [ 10293-06-8 ]
  • (1R,3R,4R)-3-(Anthracene-9-carbonyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With samarium diiodide In tetrahydrofuran at 0℃; for 2h;
  • 12
  • [ 10293-06-8 ]
  • ketopinic acid chloride [ No CAS ]
  • (1R,3R,4R)-3-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carbonyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With samarium diiodide In tetrahydrofuran at 0℃; for 2.5h;
  • 13
  • [ 10293-06-8 ]
  • [ 98-88-4 ]
  • (1R,3R,4R)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With samarium diiodide In tetrahydrofuran at 0℃; for 2.3h;
  • 14
  • [ 10293-06-8 ]
  • [ 874-60-2 ]
  • (1R,3S,4R)-1,7,7-Trimethyl-3-(4-methyl-benzoyl)-bicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With samarium diiodide In tetrahydrofuran at 0℃; for 3h;
  • 15
  • [ 10293-06-8 ]
  • [ 122-04-3 ]
  • (1R,3S,4R)-1,7,7-Trimethyl-3-(4-nitro-benzoyl)-bicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With samarium diiodide In tetrahydrofuran at 0℃; for 2h;
  • 16
  • [ 10293-06-8 ]
  • [ 75-36-5 ]
  • (1R,3S,4R)-3-Acetyl-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With samarium diiodide In tetrahydrofuran at 0℃; for 2.5h;
  • 17
  • [ 10293-06-8 ]
  • [ 1079-66-9 ]
  • [ 131339-30-5 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: (1R)-3-endo-bromocamphor With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: chloro-diphenylphosphine In tetrahydrofuran at -78℃; Further stages.;
  • 18
  • [ 10293-06-8 ]
  • α-hydroxycamphor [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 % Chromat. With triethylamine; potassium iodide In acetone at 20℃; for 72h; Irradiation;
  • 19
  • [ 10293-06-8 ]
  • [ 78386-38-6 ]
  • (1R,3R,4R)-1,7,7-Trimethyl-3-(2-oxo-2-phenyl-ethyl)-bicyclo[2.2.1]heptan-2-one [ No CAS ]
  • (1R,3S,4R)-1,7,7-Trimethyl-3-(2-oxo-2-phenyl-ethyl)-bicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-trimethyl-pyridine; 2,2'-azobis(isobutyronitrile) In benzene at 85℃; for 3h; Title compound not separated from byproducts;
  • 20
  • [ 10293-06-8 ]
  • [ 935696-86-9 ]
YieldReaction ConditionsOperation in experiment
With tritium In 1,4-dioxane for 3h;
  • 21
  • [ 10293-06-8 ]
  • [ 98-88-4 ]
  • (1R,3S,4R)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one [ No CAS ]
  • (1R,3R,4R)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With samarium diiodide In tetrahydrofuran at 20℃; Title compound not separated from byproducts;
  • 22
  • [ 10293-06-8 ]
  • 2-[(1R,2R,4R)-4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: (1R)-3-endo-bromocamphor; [Ni(o-C6H4-COO)(2,2'-bipy)] In tetrahydrofuran at 50℃; for 24h; Stage #2: With hydrogenchloride for 1h; Further stages.;
  • 23
  • [ 10293-06-8 ]
  • 3-hydroxy-3-(2-oxotetrahydrofuran-3-yl)-2-benzofuran-1(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: (1R)-3-endo-bromocamphor; [Ni(o-COC6H4COO)(2,2'-bipy)] In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: With hydrogenchloride for 1h; Further stages.;
  • 24
  • [ 10293-06-8 ]
  • (1R,2S,7R,8R)-5,6-diethyl-2-hydroxy-1,11,11-trimethyl-3-oxatricyclo[6.2.1.02,7]undec-5-en-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: (1R)-3-endo-bromocamphor; [Ni{C(Et)=C(Et)COO}(2,2'-bipy)] In tetrahydrofuran Stage #2: With hydrogenchloride for 1h; Further stages.;
  • 25
  • [ 10293-06-8 ]
  • [ 145100-50-1 ]
  • [ 868851-44-9 ]
  • 26
  • [ 10293-06-8 ]
  • (1R)-3-bromo-2-(2-methoxy-1-naphthyl)bornylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / LDA / tetrahydrofuran; heptane; ethylbenzene / -60 - 20 °C 2: 44 percent / Mg / Pd(PPh3)Cl2 / tetrahydrofuran / 10 h / 50 °C
  • 27
  • [ 10293-06-8 ]
  • (1R)-3-bromo-2-(2-methoxyphenyl)bornylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / LDA / tetrahydrofuran; heptane; ethylbenzene / -60 - 20 °C 2: 49 percent / Mg / Pd(PPh3)2Cl2 / tetrahydrofuran / 10 h / 50 °C
  • 28
  • [ 10293-06-8 ]
  • [ 899828-64-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tritium / Pd/C / dioxane / 3 h 2: diethyl ether; dioxane / Heating
  • 29
  • [ 10293-06-8 ]
  • [3-3H]-1R,2S,4R-(-)-(2-dimethylaminoethoxy)-2-phenyl-1,7,7-trimethylbicyclo[2.2.1]heptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tritium / Pd/C / dioxane / 3 h 2: diethyl ether; dioxane / Heating 3: NaH / toluene; various solvent(s) / 3 h / Heating
  • 30
  • [ 10293-06-8 ]
  • [ 104832-00-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 42 percent / chlorosulfonic acid / 0.33 h / 45 °C 2: 45 percent / KOH / dimethylsulfoxide; H2O / 2.5 h / 120 °C
Multi-step reaction with 2 steps 1: 50 percent / ClSO3H / 0.25 h / 50 °C 2: 50 percent / KOH / dimethylsulfoxide; H2O / 24 h / 100 °C
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 1 h / 55 °C 2: 47 percent / KOH / dimethylsulfoxide; H2O / 96 h / 70 °C
  • 31
  • [ 10293-06-8 ]
  • 1-Phenyl-2-((1S,3R)-2,2,3-trimethyl-cyclopentyl)-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 42 percent / chlorosulfonic acid / 0.33 h / 45 °C 2: 45 percent / KOH / dimethylsulfoxide; H2O / 2.5 h / 120 °C 3: 93 percent / CeCl3 / tetrahydrofuran / 1 h / 20 °C 4: 18 percent / 520 °C / 0.02 - 0.03 Torr 5: 98 percent / H2 / Pd(C) / methanol / 20 °C
  • 32
  • [ 10293-06-8 ]
  • [ 98672-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 4: 1) sodium naphthaleimide / 1) tetraethylene glycol dimethyl ether 5: 85 percent / Li, NH3 / propan-2-ol; tetrahydrofuran / 2 h / -78 °C 6: 1) Hg(NO3)2, 2) NaBH4, 14N NaOH / 1) CH2Cl2, RT, 4h, 2) RT, 2h
Multi-step reaction with 6 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 4: 1) sodium naphthaleimide / 1) tetraethylene glycol dimethyl ether, THF, -78 deg, 2) -78 to -40 deg C 5: 85 percent / Li, NH3 / propan-2-ol; tetrahydrofuran / 2 h / -78 °C 6: 1) Hg(NO3)2, 2) NaBH4, 14N NaOH / 1) CH2Cl2, RT, 4h, 2) RT, 2h
  • 33
  • [ 10293-06-8 ]
  • [ 28974-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 93 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C 4: 82 percent / NEt3, 4-(dimethylamino)pyridine / CH2Cl2 / Ambient temperature 5: 75 percent / 1-(dimethylamino)naphthaleimide / tetrahydrofuran / 0.25 h / -78 °C
Multi-step reaction with 5 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 25 percent / Al(O-iPr)3 / propan-2-ol / 96 h / 90 °C 4: 82 percent / NEt3, 4-(dimethylamino)pyridine / CH2Cl2 / Ambient temperature 5: 75 percent / 1-(dimethylamino)naphthaleimide / tetrahydrofuran / 0.25 h / -78 °C
  • 34
  • [ 10293-06-8 ]
  • [ 129704-45-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 93 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C 4: MsCl, NEt3, 4-dimethylaminopyridine
Multi-step reaction with 4 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 25 percent / Al(O-iPr)3 / propan-2-ol / 96 h / 90 °C 4: MsCl, NEt3, 4-dimethylaminopyridine
  • 35
  • [ 10293-06-8 ]
  • [ 122763-79-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 4: 1) sodium naphthaleimide / 1) tetraethylene glycol dimethyl ether 5: 85 percent / Li, NH3 / propan-2-ol; tetrahydrofuran / 2 h / -78 °C
Multi-step reaction with 5 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 4: 1) sodium naphthaleimide / 1) tetraethylene glycol dimethyl ether, THF, -78 deg, 2) -78 to -40 deg C 5: 85 percent / Li, NH3 / propan-2-ol; tetrahydrofuran / 2 h / -78 °C
  • 36
  • [ 10293-06-8 ]
  • [ 129704-42-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 93 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C
Multi-step reaction with 3 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 25 percent / Al(O-iPr)3 / propan-2-ol / 96 h / 90 °C
  • 37
  • [ 10293-06-8 ]
  • [ 129704-43-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 93 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C 4: 82 percent / NEt3, 4-(dimethylamino)pyridine / CH2Cl2 / Ambient temperature
Multi-step reaction with 4 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 25 percent / Al(O-iPr)3 / propan-2-ol / 96 h / 90 °C 4: 82 percent / NEt3, 4-(dimethylamino)pyridine / CH2Cl2 / Ambient temperature
  • 38
  • [ 10293-06-8 ]
  • [ 129704-46-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 93 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C 4: 1) n-BuLi / 1) THF, -78 deg C, 30 min, 2a) -78 deg C, 20 min, 2b) -78 to -20 deg C 5: 85 percent / sodium 1-(dimethylamino)naphthaleimide / tetrahydrofuran / 0.25 h / -78 °C
Multi-step reaction with 5 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 25 percent / Al(O-iPr)3 / propan-2-ol / 96 h / 90 °C 4: 1) n-BuLi / 1) THF, -78 deg C, 30 min, 2a) -78 deg C, 20 min, 2b) -78 to -20 deg C 5: 85 percent / sodium 1-(dimethylamino)naphthaleimide / tetrahydrofuran / 0.25 h / -78 °C
  • 39
  • [ 10293-06-8 ]
  • exo-9-bromobornan-2-ol mesylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 93 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C 4: 1) n-BuLi / 1) THF, -78 deg C, 30 min, 2a) -78 deg C, 20 min, 2b) -78 to -20 deg C
Multi-step reaction with 4 steps 1: 63 percent / Br2, chlorosulfonic acid / 5 h / 25 °C 2: 60 percent / Zn, HOAc / 2 h / 25 °C 3: 25 percent / Al(O-iPr)3 / propan-2-ol / 96 h / 90 °C 4: 1) n-BuLi / 1) THF, -78 deg C, 30 min, 2a) -78 deg C, 20 min, 2b) -78 to -20 deg C
  • 40
  • [ 10293-06-8 ]
  • [ 514-12-5 ]
YieldReaction ConditionsOperation in experiment
84% With bromine at 50℃; for 24h; Darkness; (1R, 4S)-3,3-Dibromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 1811,12,13,14 Method A:12 endo-(+)-3-Bromocamphor 11 (10 g, 43.4 mmol) was placed in a flask wrapped in tin foil to exclude light and bromine (3.28 mL, 64.1 mmol) was added. The flask was heated at ca. 50 oC for 24 h. The flask was allowed to cool to room temperature and diluted with ether (200 mL). The solution was washed with water (100 mL) and the aqueous phase was extracted with ether (2 50 mL). The combined organic extracts were washed with satd. aq. sodium sulfite (2 100 mL) until colorless, and dried and evaporated to yield an oil which was taken up in acetic acid (60 mL) and added dropwise to ice/water (ca. 600 mL). The resulting precipitate was filtered and washed with water to afford the title compound as a yellow solid (11.39 g, 84 %). m.p.: 50-51 oC (from acetic acid); Lit.14: 54-55 oC. [α]D (c 1.72, 95 % EtOH, 27 oC) +36.2; Lit.12: (c 1.67, 95 % EtOH, 25 oC) +37.1. IR max (N) 2924, 1765 (C=O), 1459, 1375, 1315, 1294, 1262, 1236, 1180, 1142, 1112, 1019, 1001, 940, 911, 859, 811, 775, 696, 647 cm-1. 1H NMR (400.1 MHz; CDCl3; Me4Si): 1.01 (3H, s, 1-CH3), 1.11 (3H, s, 7-CH3), 1.23 (3H, s, 7-CH3), 1.61-1.66 (2H, m), 2.03-2.12 (1H, m), 2.28-2.35 (1H, m), 2.82 (1H, d, 3J = 4.0, 4-CH) ppm. 13C NMR (100.6 MHz): δ 9.9 (1-CH3), 22.0 (7-CH3), 23.6 (7-CH3), 28.5 (C-5), 28.5 (C-6), 45.6 (C-7), 57.2 (C-1), 58.8 (C-4), 63.0 (C-3), 206.2 (C-2) ppm. HRMS (CI) m/z 332.9292: calculated for [C10H14OBr2 + Na]+ 332.9289.
With bromine
  • 41
  • [ 10293-06-8 ]
  • [ 5344-58-1 ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid at 50℃; for 3h; Ammonium (1R, 3S, 4S, 7R)-(3-bromo-1,7-dimethyl-2-oxobicyclo[2.2.1]hept-7-yl)methanesulfonate 126,7 Chlorosulfonic acid (7.88 mL, 119 mmol) was added to endo-(+)-3-bromocamphor 11 (18.35 g, 79 mmol) in a 3 neck flask. After the initial evolution of hydrogen chloride had ceased the solution was heated at 50 oC with stirring for 3 h. The solution was then allowed to cool to room temperature, carefully quenched with water (100 mL) and then carefully neutralized with conc. ammonium hydroxide soln. until basic to litmus. The solution was extracted with ether (100 mL) and the aqueous phase was evaporated to dryness. The resulting solid was triturated with boiling ethanol (ca. 200 mL) and filtered and the insoluble solids were washed with boiling ethanol. The filtrate was evaporated to yield a light brown solid (13.3 g). Recrystallization from water afforded the title compound as a white solid (4.68 g). Evaporation of the mother liquor and recrystallization of the resulting solid from water yielded an additional 1.17 g of product. Total yield: 5.85 g, 22 %. The organic phase was dried and evaporated to yield unreacted endo-(+)-3-bromocamphor 11 (7.75 g). m.p.: 278-280 oC (from H2O); Lit.8: 284 oC. [α]D (c 1.14, H2O, 25 oC) +82.8; Lit.9: (c 2 g in 50 ml, H2O, 22 oC) +85.2. IR max (N) 3174 (NH4+), 2917, 1752 (C=O), 1460, 1376, 1292, 1257, 1185, 1160 (SO2), 1042 (SO2), 1006, 837, 757, 725 cm-1. 1H NMR (400.1 MHz; D2O): 0.86 (3H, s, 1-CH3), 1.07 (3H, s, 7-CH3), 1.26-1.33 (1H, m), 1.70-1.78 (1H, m), 1.90-2.02 (2H, m), 2.82 (1H, d, 2J = 14.5, CH2SO3NH4), 2.89 (1H, t, 3J = 4.0, 4-CH), 3.18 (1H, d, 2J = 14.5, CH2SO3NH4), 4.86 (1H, d, 3J = 4.5, 3-CH exo) ppm. 13C NMR (100.6 MHz; D2O): δ 8.2 (1-CH3), 16.4 (7-CH3), 21.0 (C-5), 29.3 (C-6), 46.4 (C-4), 46.6 (C-7), 52.7 (C-3), 53.3 (CH2SO3NH4), 59.8 (C-1), 217.6 (C-2) ppm.
  • 42
  • [ 10293-06-8 ]
  • [ 62-53-3 ]
  • [ 28627-52-3 ]
YieldReaction ConditionsOperation in experiment
16% at 170 - 175℃; for 24h; Schlenk technique; General procedure for synthesis of debrominated imines 2A-F General procedure: A mixture of endo-(+)-3-bromocamphor (1.156 g,5 mmol) and corresponding amine (50 mmol) in a 25 mLround-bottomed flask was heated at 130-135°C in an oilbath for 12 or 24 h. After removal of the excess of the amine under reduced pressure, 30 mL of water were added and the mixture was extracted with ether (40 mL). The organiclayer was washed with water (2 × 30 mL). After drying with anhydrous sodium sulfate, the solvent was evaporated and pure compounds were isolated by column chromatography on silica gel using different eluent mixtures.
  • 43
  • [ 111-26-2 ]
  • [ 10293-06-8 ]
  • N-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)hexan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% for 24h; Schlenk technique; Reflux; General procedure for synthesis of debrominated imines 2A-F General procedure: A mixture of endo-(+)-3-bromocamphor (1.156 g,5 mmol) and corresponding amine (50 mmol) in a 25 mLround-bottomed flask was heated at 130-135°C in an oilbath for 12 or 24 h. After removal of the excess of the amine under reduced pressure, 30 mL of water were added and the mixture was extracted with ether (40 mL). The organiclayer was washed with water (2 × 30 mL). After drying with anhydrous sodium sulfate, the solvent was evaporated and pure compounds were isolated by column chromatography on silica gel using different eluent mixtures.
  • 44
  • [ 10293-06-8 ]
  • [ 108-91-8 ]
  • N-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)cyclohexanamine-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% for 24h; Schlenk technique; Reflux; General procedure for synthesis of debrominated imines 2A-F General procedure: A mixture of endo-(+)-3-bromocamphor (1.156 g,5 mmol) and corresponding amine (50 mmol) in a 25 mLround-bottomed flask was heated at 130-135°C in an oilbath for 12 or 24 h. After removal of the excess of the amine under reduced pressure, 30 mL of water were added and the mixture was extracted with ether (40 mL). The organiclayer was washed with water (2 × 30 mL). After drying with anhydrous sodium sulfate, the solvent was evaporated and pure compounds were isolated by column chromatography on silica gel using different eluent mixtures.
  • 45
  • [ 10293-06-8 ]
  • [ 141-43-5 ]
  • [ 478011-94-8 ]
YieldReaction ConditionsOperation in experiment
73% at 130 - 135℃; for 12h; Schlenk technique; General procedure for synthesis of debrominated imines 2A-F General procedure: A mixture of endo-(+)-3-bromocamphor (1.156 g,5 mmol) and corresponding amine (50 mmol) in a 25 mLround-bottomed flask was heated at 130-135°C in an oilbath for 12 or 24 h. After removal of the excess of the amine under reduced pressure, 30 mL of water were added and the mixture was extracted with ether (40 mL). The organiclayer was washed with water (2 × 30 mL). After drying with anhydrous sodium sulfate, the solvent was evaporated and pure compounds were isolated by column chromatography on silica gel using different eluent mixtures.
  • 46
  • [ 10293-06-8 ]
  • [ 107-15-3 ]
  • C12H22N2 [ No CAS ]
  • [ 76184-18-4 ]
YieldReaction ConditionsOperation in experiment
1: 61% 2: 18% for 12h; Schlenk technique; Reflux; Overall yield = 79 %; General procedure for synthesis of debrominated imines 2A-F General procedure: A mixture of endo-(+)-3-bromocamphor (1.156 g,5 mmol) and corresponding amine (50 mmol) in a 25 mLround-bottomed flask was heated at 130-135°C in an oilbath for 12 or 24 h. After removal of the excess of the amine under reduced pressure, 30 mL of water were added and the mixture was extracted with ether (40 mL). The organiclayer was washed with water (2 × 30 mL). After drying with anhydrous sodium sulfate, the solvent was evaporated and pure compounds were isolated by column chromatography on silica gel using different eluent mixtures.
  • 47
  • [ 358-23-6 ]
  • [ 10293-06-8 ]
  • [ 868851-44-9 ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: (1R)-3-endo-bromocamphor With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; diethyl ether; hexane at -78℃; for 0.5h; Stage #2: trifluoromethylsulfonic anhydride In tetrahydrofuran; diethyl ether; hexane at -78℃; for 1h;
  • 48
  • [ 52744-72-6 ]
  • [ 10293-06-8 ]
  • [ 64-19-7 ]
  • [2-({(2Z)-3-bromo-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene}amino)phenyl](diphenyl)methyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% at 95 - 98℃; for 1.5h; Diphenyl[2-({(2E)-1,7,7-trimethylbicyclo[2,2,1]-hept-2-ylidene}amino)phenyl]methyl acetate (6a). General procedure: A mixture of 0.69 g (2.5 mmol) of amine 1 and 0.38 g(2.5 mmol) of camphor in 4 mL (70 mmol) of glacialacetic acid was heated on a boiling water bath atvigorous stirring for 1.5 h. On completion of thereaction (TLC monitoring) the reaction mixture wascooled, the separated precipitate was filtered off,recrystallized from ethanol, and dried.
  • 49
  • [ 10293-06-8 ]
  • (2′,6′-dimethoxybiphenyl-2-yl)phenylphosphine chloride [ No CAS ]
  • C30H33O3P [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: (1R)-3-endo-bromocamphor With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: (2′,6′-dimethoxybiphenyl-2-yl)phenylphosphine chloride In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;
  • 50
  • [ 10293-06-8 ]
  • [ 644-97-3 ]
  • 2-(2-bromophenyl)-1,3-difluorobenzene [ No CAS ]
  • C28H27F2OP [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% Stage #1: (1R)-3-endo-bromocamphor With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Dichlorophenylphosphine In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: 2-(2-bromophenyl)-1,3-difluorobenzene Further stages;
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