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Product Details of [ 24036-52-0 ]

CAS No. :24036-52-0
Formula : C8H6BrNO2
M.W : 228.04
SMILES Code : BrC1=CC2=C(C=C1)OCC(N2)=O
MDL No. :MFCD00461173
InChI Key :UQCFMEFQBSYDHY-UHFFFAOYSA-N
Pubchem ID :16218142

Safety of [ 24036-52-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 24036-52-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 50.96
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

38.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.84
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.57
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.21
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.26
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.18
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.61

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.61
Solubility 0.556 mg/ml ; 0.00244 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.99
Solubility 2.36 mg/ml ; 0.0103 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.49
Solubility 0.074 mg/ml ; 0.000324 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.58 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.14

Application In Synthesis of [ 24036-52-0 ]

* 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 [ 24036-52-0 ]

[ 24036-52-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 24036-52-0 ]
  • [ 105655-01-4 ]
YieldReaction ConditionsOperation in experiment
100% INTERMEDIATE 13; 6-Bromo-3,4-dihydro-2H-benzo[l.,4]oxazine; Borane-TetaF ( 13.2 mL of a 1 M solution in TetaF, 13.2 mmol) was added portionwise to Intermediate 6 (2.0 g, 8.0 mmol) in TetaF (50 mL) at r.t. The resulting solution was stirred at r.t. for 10 min, heated to reflux for 1 h and then allowed to cool to r.t. The reaction was cooled in an ice bath and quenched with water (20 mL) and 2N aqueous sodium hydroxide solution (2OmL). The solvent was removed in vacuo and the resulting mixture diluted with water (100 mL). It was extracted with EtOAc (10OmL), washed with brine (10OmL), dried (MgSO4), filtered and concentrated in vacuo to yield the title compound as a brown oil (2 g, quant). deltaeta (DMSO-d6) 3.36-3.44 (2H, m), 3.81 (IH, br s), 4.18-4.25 (2H, m), 6.68 (3H, m).
100% With borane-THF; In tetrahydrofuran; at 20℃; for 1.16667h;Heating / reflux; Borane-TetaF (13.2 mL, IM solution in TetaF, 13.2 mmol) was added portionwise to Intermediate 37 (2.0 g, 8.0 mmol) in TetaF (50 mL) at r.t. The resulting mixture was stirred at r.t. for 10 minutes, heated to reflux for 1 h and then allowed to cool to r.t. The reaction mixture was cooled to 00C and quenched with water (20 mL) and aqueous 2N NaOH (20 mL). The solvent was removed in vacuo and the resulting mixture diluted with water (100 mL). The aqueous fraction was extracted with EtOAc (100 mL), washed with brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to yield the title <n="52"/>compound (2 g, quantitative) as a brown oil. deltaH (DMSOd6) 6.68 (3H, m), 4.25-4.18 (2H, m), 3.81 (IH, br. s), 3.44-3.36 (2H, m).
100% INTERMEDIATE 106-Bromo-3,4-dihvdro-2H-benzo[ 1 ,4]oxazineBorane-THF (13.2 mL of a IM solution in THF, 13.2 mmol) was added portionwise to Intermediate 8 (2.0 g, 8.0 mmol) in THF (50 mL) at r.t. The resulting solution was stirred at r.t. for 10 minutes, heated to reflux for 1 h and then allowed to cool to r.t. The reaction was cooled in an ice bath and quenched with water (20 mL) and 2N aqueous sodium hydroxide solution (20 mL). The solvent was removed in vacuo and the resulting mixture diluted with water (100 mL). It was extracted with EtOAc (100 mL), <n="99"/>washed with brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to yield the title compound (2 g, quantitative) as a brown oil. deltaH (DMSO-d6) 6.68 (3H, m), 4.18- 4.25 (2H, m), 3.81 (IH, br s), 3.36-3.44 (2H, m).
100% Borane-THF (13.2 mL, IM solution in THF, 13.2 mmol) was added portionwise to Intermediate 5 (2.0 g, 8.0 mmol) in THF (50 mL) at r.t. The resulting solution was stirred at r.t. for 10 minutes, heated to reflux for 1 h and then allowed to cool to r.t. The reaction mixture was cooled to 00C and quenched with water (20 mL) and aqueous 2N NaOH (20 mL). The solvent was removed in vacuo and the resulting mixture diluted with water (100 mL). The aqueous fraction was extracted with EtOAc (100 mL), washed with brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to yield the title compound (2 g, quantitative) as a brown oil. deltaH (DMSO-d6) 6.68 (3H, m), 4.25-4.18 (2H, m), 3.81 (IH, br. s), 3.44-3.36 (2H, m).
100% To a stirred solution of Intermediate 32 (2.0 g, 8.0 mmol) in TetaF (50 mL) was added borane-TetaF (13.2 mL, IM solution in TetaF, 13.2 mmol) portionwise. The reaction mixture was stirred at r.t. for 10 minutes, then heated to reflux for 1 h and allowed to cool to r.t. The reaction mixture was cooled to 00C and quenched with water (20 mL), then 2M aqueous NaOH (20 mL), and concentrated in vacuo. Water (100 mL) and EtOAc (100 mL) were added and the layers separated. The organic fraction was washed with <n="105"/>brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound (2 g, quantitative) as a brown oil. deltaH (DMSOd6) 6.68 (3 H, m), 4.25-4.18 (2H, m), 3.81 (IH, br. s), 3.44-3.36 (2H, m).
93% With dimethylsulfide borane complex; In tetrahydrofuran; for 3h;Inert atmosphere; Reflux; To a solution of 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (400 mg, 1.75 mmol) in anhydrous tetrahydrofuran (3 mL) under a nitrogen atmosphere was added a 1M solution of borane dimethyl sulfide complex in tetrahydrofuran (7.0 mL, 7.0 mmol) slowly. The resulting solution was refluxed for 3 hours. Then, the reaction mixture was cooled to ambient temperature and carefully quenched with the addition of methanol (10 mL). Next, the reaction mixture was heated to reflux for 10 minutes, and then the reaction mixture was cooled and concentrated in vacuo to provide a residue. The residue was redissolved in ethyl acetate, washed with water, brine, dried with sodium sulfate, filtered and concentrated in vacuo to yield title compound. The title compound was used in Part IV below without purification. (350 mg, 93% yield) ESI m/z 214.03, 216.0 (M+H).
88% Example 48; lambda/-{2-chloro-5-[4-(phenylmethyl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]-3- pyridinyl}benzenesulfonamide; a) 6-bromo-3 ,4-dihy dro-2H- 1 ,4-benzoxazine; 6-Bromo-2H-l,4-benzoxazin-3(4H)-one (2.085 g, 9.143 mmol) was suspended in dry TetaF (20 mL) and placed under nitrogen with stirring and to this was added 1 M BH3-THF complex (3.143 g, 36.572 mmol, 36.52 mL) over 5 minutes. Addition causes the reaction to become homogeneous. After 70 minutes, the reaction was cooled to O0C and made acidic by addition of 3N HCl (109 mL). Addition of acid causes vigorous bubbling. After the addition was completed, the reaction was refluxed for 10 minutes and then cooled and made basic by addition of 6N NaOH. The basified reaction was extracted with EtOAc (3 x 100 mL), dried over Na2SO4, filtered, and the concentrated filtrate was purified by flash chromatography on silica gel (.00% CH2Cl2) to give the title compound (1.713 g, 88%) as a pale yellow oil. MS(ES)+ m/e 214 [M+H].
87% With borane-THF; In tetrahydrofuran;Inert atmosphere; Cooling with ice; Reflux; [Synthesis of Compound E4] (0133) Compound E3 (1.0 g, 4.4 mmol, 1 Eq) was dissolved in THF (20 mL) in an argon atmosphere, and placed on an ice bath. A THF solution of 1 M borane-THF complex (7.0 mL, 7.0 mmol, 1.6 Eq) was added and the combination was stirred overnight while heating and refluxing. The reaction system was returned to room temperature, methanol was added in small amounts, and the solvent was removed under reduced pressure. The reaction system was then diluted by ethyl acetate, and the organic layer was washed by saturated sodium hydrogen carbonate aqueous solution and saturated saline, dried by anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue obtained was purified by medium-pressure silica gel chromatography (eluent: dichloromethane/methanol=98/2), and the target compound E4 (817 mg, 87%) was obtained as a colorless liquid. (0134) 1H NMR (CDCl3): delta 6.71 (dd, J=2.3 Hz, 8.4 Hz, 1H), 6.68 (d, J=2.3 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H), 4.20 (t, J=4.4 Hz, 2H), 3.80 (br s, 1H), 3.38 (t, J=4.4 Hz, 2H).; 13C NMR (CDCl3): delta 143.1 (C), 135.2 (C), 121.2 (CH), 118.1 (CH), 117.7 (CH), 113.2 (C), 65.1 (CH2), 40.6 (CH2).; HRMS-ESI (m/z): [M+H]+ calcd for C8H9BrNO: 213.98620. found: 213.98626 (-0.1 mDa, -0.3 ppm).
With borane-THF; In tetrahydrofuran; for 14h;Reflux; Step II: To a stirred solution of 6-bromo-2H-1,4-benzoxazin-3(4H)-one (10 g, 43.85 mmol) in THF (25 ml) was added 1.0 M borane-tetrahydrofuran complex in THF (153.5 ml, 153.48 mmol) and refluxed for 14 h. The reaction mixture was cooled to room temperature, quenched with methanol (50 ml) and concentrated under reduced pressure. The resulting residue was taken in ethyl acetate (100 ml), washed with aqueous saturated sodium bicarbonate solution (100 ml), water (100 ml), brine (100 ml), dried over sodium sulphate, concentrated and purified by silica gel column chromatography (5% ethyl acetate in hexane) to provide 6-bromo-3,4-dihydro-2H- benzop^oxazine (8.5 g).
3.2 g With borane-THF; In tetrahydrofuran; at 0℃; for 3h;Reflux; 6-bromo-3,4-dihydro-2H-benzo[6] [l,4]oxazine (2): To a stirred solution of 6- bromo-2H-benzo[6][l,4]oxazin-3(4H)-one (7 g, 30.8 mmol) in THF (20 mL) was added 1M borane in THF (15.41 mL) at 0 C and stirred for 3 h at reflux temperature. After completion of the reaction, methanol (2 mL) was added to the reaction mixture at 0 C and stirred for 2 h at reflux. After completion of the reaction, cone. HC1 (2 mL) was added to reaction mixture at 0 C and again stirred for 2 h at reflux. The reaction mixture was then neutralized with 2N NaOH solution at 0 C and extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude compound was purified by column chromatography (100-200 mesh silica gel, 15% ethyl acetate in pet. ether as eluent) to afford 2 (3.2 g, 49% yield) as a brown solid. MS m/z (M+H): 214.4
With borane-THF; In tetrahydrofuran; at 0℃;Reflux; Compound 7-2 (22 g, 0.1 mol) was dissolved in tetrahydrofuran (200 ml) and a solution of BH3 / tetrahydrofuran (1.0 M, 200 ml) was added dropwise at 0 C. The mixture was then stirred under reflux overnight. Then slowly at 0 reaction was quenched with methanol. The mixture was concentrated to give a crude product was used directly in the next step.

  • 2
  • [ 24036-52-0 ]
  • [ 557-21-1 ]
  • [ 134997-74-3 ]
YieldReaction ConditionsOperation in experiment
89% With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; A degassed suspension of commercially available 6-Bromo-4H- benzo[l ,4]oxazin-3-one (8.39 g), Zn(CN)2 (3.46 g) and Pd(PPh3)4 (2.13 g) in DMF (70 mL) was stirred in a oil bath (80C) overnight. The mixture was cooled to room temperature and then poured into water (500 mL). The precipitate was collected by suction, air dried, washed with pentane, dissolved in CH2Cl2ZMeOH (1 : 1), filtered through an silica pad and concentrated to yield a yellow solid (5.68 g, 89%). [MH]+ = 175.
89% tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; Step A; A degassed suspension of commercially available 6-Bromo-4H- benzo[l,4]oxazin-3-one (8.39 g), Zn(CN)2 (3.46 g) and Pd(PPh3)4 (2.13 g) in DMF (70 mL) was stirred in a oil bath (80 C) overnight. The mixture was cooled to room temperature and then poured into water (500 mL). The precipitate was collected by suction, air dried, washed with pentane, dissolved in CH2Cl2ZMeOH (1:1), filtered through an silica pad and concentrated to yield a yellow solid (5.68 ^ 89 0ZoJ MH+ = ITS).
89% tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; Step A. A degassed suspension of commercially available 6-Bromo-4H-benzo[l,4]oxazin-3-one (8.39 g), Zn(CN)2 (3.46 g) and Pd(PPh3)4 (2.13 g) in DMF (70 mL) was stirred in a oil bath (80 C) overnight. The mixture was cooled to room temperature and then poured into water (500 mL). The precipitate was collected by suction, air dried, washed with pentane, dissolved in CH2Cl2/Me0H (1:1), filtered through a silica pad and concentrated to yield a the title compound (5.68 g, 89%). [MH]+ = 175.
  • 3
  • [ 24036-52-0 ]
  • copper(l) cyanide [ No CAS ]
  • [ 134997-74-3 ]
YieldReaction ConditionsOperation in experiment
26% In 1-methyl-pyrrolidin-2-one; at 200℃; for 4h;Inert atmosphere; Microwave irradiation; The synthesis of compound (10) is based on published literature procedure (Gege, C; et al. J. Med. Chem. 55(2), 709-716, (2012)). First commercially available 6-bromo-4-H-benzo[l,4]oxazine-3-one (9) (4.3 mmole) (Alfa Aesar) is added to a thick walled glass vessel containing a stir bar. To the vessel is then added Copper (I) cyanide (12.2 mmoles) (obtained from Aldrich). The vessel was placed under vacuum then nitrogen atmosphere and then syringed 15 ml of anhydrous N-methylpyrolidinone and solution heated under closed nitrogen atmosphere using microwave radiation at 200 C for 4 hours. The solution was then evaporated under reduced pressure to give an oil. To the oil was added 150 ml of ethylacetate and the organic layer washed with 10% citric acid and then both layers filtered though a celite plug and then the organic separated and washed with saturated NaHC03 and then saturated NaCl. The organic layer was separated and dried over anhydrous magnesium sulphate, filtered and the volatile components removed under reduced pressure to give a solid which was purified by column chromatography (Si02, methylene chloride: methanol 95:5) to give 0.2 grams (26% yield) of 3-Oxo-3,4-dihydro-2H- benzo[l,4]oxazine-6-carbonitrile (10). lH NMR (300 MHz, d6-DMSO) delta 4.69 (s, 2H), 7.08 (d, 1H, J = 8.4 Hz), 7.18 (s, 1 H), 7.29 (d, 1H, J = 8.4 Hz), 10.90 (s, 1H). LC-MS (M-H) 173.
  • 4
  • [ 557-21-1 ]
  • [ 24036-52-0 ]
  • [ 134997-74-3 ]
YieldReaction ConditionsOperation in experiment
3.4 g With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; for 16h;Inert atmosphere; To a stirred solution of 6-bromo-2H-benzo[b][1 ,4]oxazin-3(4H)-one (3.Og, 13.2 mmol) in N,N15 dimethylformamide (35 mL) was added zinc cyanide (1 .24 g, 10.5 mmol, 668 iL) andtetrakis(triphenylphosphine)palladium(0) (760 mg, 658 imol) under nitrogen. The mixture was then stirred at 80 C for 16 h, cooled to room temperature, and extracted with ethyl acetate (60 mL x 4). The combined organic layers were washed with saturated aqueous sodium chloride solution (15 mL) and dried over anhydrous sodium sulfate. The combined organic layers were concentrated to dryness to givethe crude product. The crude product was further purified by trituration in ethyl acetate and used in the next step without further purification. 3-oxo-3 ,4-di hydro-2H-benzo[b][1 ,4]oxazine-6-carbonitrile (3.40 g) was obtained as a white solid. LCMS (ESI) m/z: [M+H]÷ 175.0.
 

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 24036-52-0 ]

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