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[ CAS No. 230299-46-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 230299-46-4
Chemical Structure| 230299-46-4
Structure of 230299-46-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 230299-46-4 ]

CAS No. :230299-46-4 MDL No. :MFCD03490499
Formula : C14H28B2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :CZLUUPDJUFXXHF-UHFFFAOYSA-N
M.W : 281.99 Pubchem ID :15352670
Synonyms :

Calculated chemistry of [ 230299-46-4 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 83.3
TPSA : 36.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.98
Log Po/w (WLOGP) : 3.03
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 0.71
Consensus Log Po/w : 1.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.112 mg/ml ; 0.000398 mol/l
Class : Soluble
Log S (Ali) : -3.42
Solubility : 0.107 mg/ml ; 0.000381 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.63
Solubility : 0.0657 mg/ml ; 0.000233 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.76

Safety of [ 230299-46-4 ]

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 [ 230299-46-4 ]

* 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 [ 230299-46-4 ]

[ 230299-46-4 ] Synthesis Path-Downstream   1~85

YieldReaction ConditionsOperation in experiment
Example 31 4,4,4',4',6,6,6',6'-Octamethyl-2,2'-bi-1,3,2-dioxaborinane Synthesis of The diol 2,4-dimethyl-2,4-dihydroxypentane (1.32 g, 1 mmol) was reacted with diboronic acid (0.45 g, 0.5 mmol) in 25 ml dry THF at room temp. (procedure C without dehydrating agent). The diboronic acid dissolved to give a colourless, clear solution. The gc on a small aliquot of the reaction solution, diluted with ethyl acetate, showed only two peaks of area ratio 4:95. The weak peak corresponded to the retention time of the diol. On removing the solvent from the reaction solution under reduced pressure the product ester was obtained as a white solid. 1H nmr (D6-DMSO) delta 1.25 (s, 24H), 1.77 (s, 4H).
  • 2
  • [ 230299-46-4 ]
  • [ 884495-39-0 ]
  • [ 1198802-90-2 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; Intermediate 25 2-(Methyloxy)-5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-3-pyridinamine 5-Bromo-2-(methyloxy)-3-pyridinamine (500 mg, 2.463 mmol), potassium acetate (725 mg, 7.39 mmol), 4,4,4',4',6,6,6',6'-octamethyl-2,2'-bi-1 ,3,2-dioxaborinane (1991 mg, 7.06 mmol) and Pd(dppf)CI2 (180 mg, 0.246 mmol) were weighed to a round bottomed flask and 1 ,4-Dioxane (20 mL) was added. The reaction mixture was heated at 80 0C overnight then passed through a 5 g silica cartridge which was washed with methanol, then evaporated on to dryness. The residue was partitioned between DCM and water. The DCM layer was passed through a hydrophobic frit then evaporated to dryness. The residue was triturated with ether then filtered. The ether was evaporated and the residue was triturated with hexane, then heated at 60 0C for 1 hour before evaporation to dryness. The residue was purified through a 10g silica cartridge, eluting with DCM then 1-2% methanol in DCM. Pure fractions were combined and evaporated to dryness to afford the title compound (274 mg). LCMS (Method B) R1 1.13 min, MH+ 265.
  • 3
  • [ 230299-46-4 ]
  • [ 1198438-43-5 ]
  • [ 1198803-01-8 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 - 100℃; for 1.25h;Microwave irradiation; Intermediate 422-[(2/?,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-lambda/-[1 -methyl-6-(4,4,6,6-tetramethyl- 1 ,3,2-dioxaborinan-2-yl)-1 H-indazol-4-yl]-1 ,3-thiazole-4-carboxamide lambda/-(6-Bromo-1 -methyl-1 H-indazol-4-yl)-2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1 ,3- thiazole-4-carboxamide (500 mg, 1.077 mmol), 4,4,4',4',6,6,6',6'-octamethyl-2,2'-bi-1 ,3,2- dioxaborinane (364 mg, 1.292 mmol), Pd(dppf)CI2 (79 mg, 0.108 mmol) and potassium acetate (423 mg, 4.31 mmol) were weighed to a microwave vial. Anhydrous 1 ,4-dioxane (5 ml) was added and the reaction heated in the microwave at 80 0C for 45 min. Further catalyst (50 mg) was added and the mixture heated at 100 0C for 30 mins. The solvent was removed and the residue was partitioned between water (20 ml) and (DCM 20 ml). <n="124"/>The organic layer was collected using a hydrophobic frit and the solvent removed in vacuo. The residue was purifed by chromatography on silica (50 g cartridge) eluting with 0-100 % ethyl acetate in cyclohexane over 40 mins to give the title compound (356 mg). LCMS (Method B) R1 = 1.11 mins, MH+ = 526.
  • 4
  • [ 230299-46-4 ]
  • [ 1198437-59-0 ]
  • [ 1198437-63-6 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃; for 1.5h;Microwave irradiaiton; Intermediate 851 -(1 -Methylethyl)-lambda/-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1 ,3,2- dioxaborinan-2-yl)-2H-indazol-4-yl]-1H-pyrazole-5-carboxamide lambda/-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2/-/-indazol-4-yl]-1-(1-methylethyl)-1 /-/-pyrazole- 5-carboxamide (500 mg, 1.16 mmol), Pd(dppf)CI2 DCM adduct (94 mg, 0.115 mmol), potassium acetate (341 mg, 3.47 mmol) and 4,4,4',4 6,6,6', 6'-octamethyl-2,2'-bi-1 , 3,2- dioxaborinane (978 mg, 3.47 mmol) were combined in a microwave vial. 1 ,4-Dioxane (8 ml) was added and the mixture was heated at 80 0C for 30 min. Analysis by LCMS showed incomplete reaction so the mixture was heated again under microwave conditions for 30 min at 80 0C. Further Pd(dppf)CI2 DCM adduct (38 mg) was then added and the reaction heated for another 30 min at 80 0C. The reaction mixture was applied to the top of a silica cartridge and washed through with methanol. After removal of solvent the residue was partitioned between DCM and water and the organics concentrated in vacuo. Purification was carried out by chromatography on silica (4Og) using a gradient of 40% - 60% EtOAc in cyclohexane. Fractions containing desired product were combined, concentrated in vacuo and dried under vacuum to to afford the title compound as a pale yellow solid. LC/MS R1 1.33 min m/z 494 [MH"]. Method C
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃; for 1.5h;Inert atmosphere; Intermediate 161 -(1 -Methylethyl)-lambda/-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1 ,3,2- dioxaborinan-2-yl)-2H-indazol-4-yl]-1H-pyrazole-5-carboxamide lambda/-[6-Bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-1-(1-methylethyl)-1 /-/-pyrazole- 5-carboxamide (500 mg, 1.16 mmol), Pd(dppf)CI2 DCM adduct (94 mg, 0.115 mmol), potassium acetate (341 mg, 3.47 mmol) and 4,4,4',4',6,6,6',6'-octamethyl-2,2'-bi-1 ,3,2- dioxaborinane (978 mg, 3.47 mmol) were combined in a microwave vial. 1 ,4-Dioxane (8 ml) was added and the mixture was heated at 80 0C for 30 min. Analysis by LCMS <n="108"/>showed incomplete reaction so the mixture was heated again under microwave conditions for 30 min at 80 0C. Further Pd(dppf)CI2 DCM adduct (38 mg) was then added and the reaction heated for another 30 min at 80 0C. The reaction mixture was applied to the top of a silica cartridge and washed through with methanol. After removal of solvent the residue was partitioned between DCM and water and the organics concentrated in vacuo. Purification was carried out by chromatography on silica (4Og) using a gradient of 40% - 60% EtOAc in cyclohexane. Fractions containing desired product were combined, concentrated in vacuo and dried under vacuum to to afford the title compound as a pale yellow solid. LC/MS R1 1.33 min m/z 494 [MH"]. Method C
  • 5
  • [ 230299-46-4 ]
  • [ 1245464-56-5 ]
  • [ 1245465-31-9 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 0.5h; 6-Bromo-1-[(4-methylphenyl)sulfonyl]-1 H-indazole-4-carbonitrile (1 g, 2.66 mmol), 4,4,4', 4', 6,6,6', 6'-octamethyl-2-2'-bi-1 ,3,2-dioxaborinane (0.899 g, 3.19 mmol), potassium acetate (0.783 g, 7.97 mmol) and 1 ,1 '-bis(diphenylphosphino)ferrocene palladium (0.389 g, 0.532 mmol) were heated under microwave irradiation with 1 ,4-dioxane (15 ml) at 8O0C for 30 mins. The solvent was removed in vacuo and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The organic layer was collected and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel (100 g cartridge), eluting with 0-50% ethyl actetate in cyclohexane. The resultant residue was azeotroped in toluene and dried on the vacuum line to give the title compound as a cream solid (0.99 g). LCMS (Method A): Rt 1.53 mins, MH+ 438.
0.99 g With bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); potassium acetate; In 1,4-dioxane; at 80℃; for 0.5h;Microwave irradiation; 1-[(4-Methylphenyl)sulfonyl]-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-1H-indazole-4-carbonitrile 6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile (1 g, 2.66 mmol), <strong>[230299-46-4]4,4,4',4',6,6,6',6'-octamethyl-2-2'-bi-1,3,2-dioxaborinane</strong> (0.899 g, 3.19 mmol), potassium acetate (0.783 g, 7.97 mmol) and 1,1'-bis(diphenylphosphino)ferrocene palladium (0.389 g, 0.532 mmol) were heated under microwave irradiation with 1,4-dioxane (15 ml) at 80 C. for 30 mins. The solvent was removed in vacuo and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The organic layer was collected and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel (100 g cartridge), eluting with 0-50% ethyl actetate in cyclohexane. The resultant residue was azeotroped in toluene and dried on the vacuum line to give the title compound as a cream solid (0.99 g). LCMS (Method A): Rt 1.53 mins, MH+ 438.
  • 6
  • [ 230299-46-4 ]
  • [ 1198437-61-4 ]
  • [ 1198437-65-8 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); In 1,4-dioxane; at 80℃; for 0.5h;microwave; To 2 separate microwave vials was weighed N-[6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H- indazol-4-yl]-2-methyl-1 ,3-thiazole-4-carboxamide (1 .13 g), potassium acetate (799 mg), 4,4,4',4',6,6,6',6'-octamethyl-2,2'-bi-1 ,3,2-dioxaborinane (2.0 g) and Pd(dppf)CI2 (348 mg). To this was added 1 ,4-dioxane (17 ml) and the reaction was heated for 30 min at 80 C in the microwave. Vial 2 was heated for a further 30 min at 80 C using the microwave. Hence combined reaction mixtures were washed through a silica cartridge (10 g) with methanol, preconditioned with methanol. The solution was dried down. The solid was separated between DCM and water and the DCM layer was dried down. The material was dissolved in DCM and methanol (few drops) and adsorbed onto fluorisil then purified on the ISCO companion, silica column (80 g) using 40 - 100 % ethyl acetate in cyclohexane. Appropriate fractions were combined to give title compound, 1 .25 g. LCMS (method B) Rt = 1 .35 min, MH+ = 483.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 0.5h;Microwave irradiation; To 2 separate microwave vials was weighed N-[6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H- indazol-4-yl]-2-methyl-1 ,3-thiazole-4-carboxamide (1 .13 g), potassium acetate (799 mg), 4.4.4'.4'.6.6.6'.6'-octamethyl-2.2'-bi-1 .3,2-dioxaborinane (2.0 g) and PdCI2(dppf) (348 mg). To this was added 1 ,4-dioxane (17 ml) and the reaction was heated for 30 min at 80 C in the microwave. Heated vial 2 again for 30 min at 80 C using microwave. Hence combined reaction mixtures were washed through a silica cartridge (10 g) with methanol, preconditioned with methanol. The solution was dried down. The solid was separated between DCM and water and the DCM layer was dried down. The material was dissolved in DCM and methanol (few drops) and adsorbed onto florisil then purified on the ISCO companion, silica column (80 g) using 40 % - 100 % ethyl acetate in cyclohexane. Fractions collected were analysed for product and the appropriate ones were combined to give the title compound, 1 .25 g.LCMS (method B) Rt = 1 .35 min, MH+ = 483.
1.25 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 0.5h;Microwave irradiation; 2-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide To 2 separate microwave vials was weighed N-[6-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide (1.13 g), potassium acetate (799 mg), <strong>[230299-46-4]4,4,4',4',6,6,6',6'-octamethyl-2,2'-bi-1,3,2-dioxaborinane</strong> (2.0 g) and Pd(dppf)Cl2 (348 mg). To this was added 1,4-dioxane (17 ml) and the reaction was heated for 30 min at 80 C. in the microwave. Vial 2 was heated for a further 30 min at 80 C. using the microwave. Hence combined reaction mixtures were washed through a silica cartridge (10 g) with methanol, preconditioned with methanol. The solution was dried down. The solid was separated between DCM and water and the DCM layer was dried down. The material was dissolved in DCM and methanol (few drops) and adsorbed onto fluorisil then purified on the ISCO companion, silica column (80 g) using 40-100% ethyl acetate in cyclohexane. Appropriate fractions were combined to give title compound, 1.25 g. LCMS (method E) R=i.35 mi MH=483.
  • 7
  • [ 230299-46-4 ]
  • [ 1198437-71-6 ]
  • 1-(phenylsulfonyl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-1H-indazol-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 1h;microwave vial; This reaction was carried out in 5 separate microwave vials. Solvent was added per vial totalling 90 ml for the entire reaction. In 5 separate microwave reaction vials was introduced 6-bromo-1 -(phenylsulfonyl)-1 H-indazol-4-amine (1 .078 g x 5), potassium acetate (903 mg x 5), 4,4,4',4',6,6,6',6'-octamethyl-2,2'-bi-1 ,3,2-dioxaborinane (1.249 g x 5) and Pd(dppf)CI2 (224 mg x 5). Further to each microwave vial was added 1 , 4-dioxane (18 ml x 5). The reaction mixtures were then heated at 80 C for 60 min in the microwave. The reaction mixtures were combined and washed through a silica cartridge (20 g x 2, preconditioned with methanol) with methanol. The resulting solution was dried on the rotary evaporator. The residue was extracted with DCM, separated between DCM and water and passed through a hydrophobic frit. The DCM was dried down to afford a solid which was dissolved in DCM, adsorbed onto fluorasil and purified on the ISCO companion using a silica column (120 g). Fractions containing product were combined to give a yellow sticky gum which was refluxed in n-hexane at 80 C for 2 hours. The solid obtained was dissolved in a minimum amount of methanol, evaporated in vacuo, then dried overnight under vauum to afford the title compound, 4.85 g.LCMS (Method B); Rt = 0.96 min, MH+ = 414
  • 8
  • [ 695-12-5 ]
  • [ 230299-46-4 ]
  • CH(C6H11)CH2(BO2CH2(C(CH3)2)2)2 [ No CAS ]
  • 9
  • [ 230299-46-4 ]
  • [ 61124-61-6 ]
  • 2,2'-(3-phenylpropane-1,1-diyl)bis(4,4,6,6-tetramethyl-1,3,2-dioxaborinane) [ No CAS ]
  • 10
  • [ 230299-46-4 ]
  • [ 34266-29-0 ]
  • 2,2'-(cyclohexylmethylene)bis(4,4,6,6-tetramethyl-1,3,2-dioxaborinane) [ No CAS ]
  • 12
  • [ 119-65-3 ]
  • [ 230299-46-4 ]
  • C32H42B2N2O4 [ No CAS ]
  • 13
  • [ 230299-46-4 ]
  • [ 109790-06-9 ]
  • (+)-(S)-dimethyl(phenyl)(3-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)butyl)silane [ No CAS ]
  • 14
  • [ 695-12-5 ]
  • [ 230299-46-4 ]
  • (+)-(S)-2-(1-cyclohexylethyl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 15
  • [ 230299-46-4 ]
  • 1-(oct-7-en-1-yl)-1H-indole [ No CAS ]
  • C23H36BNO2 [ No CAS ]
  • 16
  • [ 230299-46-4 ]
  • [ 146852-13-3 ]
  • C20H30BNO2 [ No CAS ]
  • 17
  • [ 230299-46-4 ]
  • [ 46169-71-5 ]
  • C19H28BNO2 [ No CAS ]
  • 18
  • [ 230299-46-4 ]
  • 1-((hept-6-en-1-yloxy)methyl)-4-(trifluoromethyl)benzene [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-((4-(trifluoromethyl)benzyl)oxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 19
  • [ 230299-46-4 ]
  • 5-((hept-6-en-1-yloxy)methyl)benzo[d][1,3]dioxole [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-(benzo[d][1,3]dioxol-5-ylmethoxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 20
  • [ 230299-46-4 ]
  • 1-((hept-6-en-1-yloxy)methyl)-4-(trifluoromethoxy)benzene [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-((4-(trifluoromethoxy)benzyl)oxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 21
  • [ 230299-46-4 ]
  • 1-(hept-6-en-1-yloxy)naphthalene [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-(naphthalen-1-yloxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 22
  • [ 230299-46-4 ]
  • (4-((hept-6-en-1-yloxy)methyl)phenyl)(methyl)sulfane [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-((4-(methylthio)benzyl)oxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 23
  • [ 230299-46-4 ]
  • 2-((hept-6-en-1-yloxy)methyl)thiophene [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-(thiophen-2-ylmethoxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 24
  • [ 230299-46-4 ]
  • 2-((hept-6-en-1-yloxy)methyl)furan [ No CAS ]
  • (+)-(S)-2-(7-(furan-2-ylmethoxy)heptan-2-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 25
  • [ 230299-46-4 ]
  • 4-bromo-2-chloro-1-(hept-6-en-1-yloxy)benzene [ No CAS ]
  • (+)-(S)-2-(7-(4-bromo-2-chlorophenoxy)heptan-2-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 26
  • [ 230299-46-4 ]
  • 1-(hept-6-en-1-yloxy)-4-iodobenzene [ No CAS ]
  • (+)-(S)-2-(7-(4-iodophenoxy)heptan-2-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 27
  • [ 230299-46-4 ]
  • 1-(hex-5-en-1-yl)-1H-indole [ No CAS ]
  • (+)-(S)-1-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1H-indole [ No CAS ]
  • 28
  • [ 230299-46-4 ]
  • 1-(hex-5-en-1-yl)-1H-indole-3-carbonitrile [ No CAS ]
  • (+)-(S)-1-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1H-indole-3-carbonitrile [ No CAS ]
  • 29
  • [ 230299-46-4 ]
  • methyl 1-(hex-5-en-1-yl)-1H-indole-3-carboxylate [ No CAS ]
  • methyl (+)-(S)-1-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1H-indole-3-carboxylate [ No CAS ]
  • 30
  • [ 230299-46-4 ]
  • [ 1334228-85-1 ]
  • (+)-(S)-1-(6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)heptyl)-1H-indole [ No CAS ]
  • 31
  • [ 230299-46-4 ]
  • 9-(hex-5-en-1-yl)-1,2,3,9-tetrahydro-4H-carbazol-4-one [ No CAS ]
  • (+)-(S)-9-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1,2,3,9-tetrahydro-4Hcarbazol-4-one [ No CAS ]
  • 32
  • [ 230299-46-4 ]
  • 9-(hept-6-en-1-yl)-9H-carbazole [ No CAS ]
  • (+)-(S)-9-(6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)heptyl)-9H-carbazole [ No CAS ]
  • 33
  • [ 230299-46-4 ]
  • 1-(hept-6-en-1-yl)-1H-pyrrole [ No CAS ]
  • (+)-(S)-1-(6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)heptyl)-1H-pyrrole [ No CAS ]
  • 34
  • [ 230299-46-4 ]
  • 1-(hex-5-en-1-yl)-1H-indazole [ No CAS ]
  • (+)-(S)-1-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1H-indazole [ No CAS ]
  • (+)-1-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1H-indazole [ No CAS ]
  • 35
  • [ 230299-46-4 ]
  • 1-(hex-5-en-1-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • (+)-(S)-1-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 36
  • [ 230299-46-4 ]
  • 2-(hex-5-en-1-yloxy)pyridine [ No CAS ]
  • (+)-(S)-2-((5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)oxy)pyridine [ No CAS ]
  • 37
  • [ 230299-46-4 ]
  • N-tritylpent-4-en-1-amine [ No CAS ]
  • (+)-(S)-4-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-N-tritylpentan-1-amine [ No CAS ]
  • 38
  • [ 230299-46-4 ]
  • [ 768-56-9 ]
  • C17H27BO2 [ No CAS ]
  • (+)-4,4,6,6-tetramethyl-2-(4-phenylbutan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(4-phenylbutan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
YieldReaction ConditionsOperation in experiment
In a glove box, CuCl (0.4 mg, 0.004 mmol, 2.0 mol%) was added to an 8 mL vial.Compound 16 (2.9 mg, 0.004 mmol, 2.0 mol%), tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL),After the reaction mixture was reacted at room temperature for 1 hour, B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added.After the mixture was allowed to continue to react at room temperature for 30 minutes, compound S1 (0.2 mmol) and MeOH (16 uL, 0.4 mmol,2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.The crude product has a regioselectivity of (Marsh: anti-Martens) 79:21, product anhydrous oil, yield = 54%, HPLC(OD-H, 5% IPA in hexanes, 1 mL/min, 220 nm), ee = 84%:
  • 39
  • [ 230299-46-4 ]
  • [ 768-56-9 ]
  • C17H27BO2 [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(4-phenylbutan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In a glove box, CuCl (0.4 mg, 0.004 mmol, 2.0 mol%) was added to an 8 mL vial.1,3-bis(2,6-bis((R)-1-(3,5-di-tert-butylphenyl)ethyl)-2-methylphenyl)-4,5-dihydro-1H -imidazole hydrochloride (3.6 mg,0.004 mmol, 2.0 mol%),tBuONa (28.8 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL),After the reaction mixture was reacted at room temperature for 1 hour, B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added.After the reaction mixture was continued to react at room temperature for 30 minutes, compound S1 (26.4 mg, 0.2 mmol) and MeOH (16 uL, 0.4 mmol,2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol. The crude product has a regioselectivity of (Marsh: anti-Martens) 90:10, product anhydrous oil, yield = 80%, HPLC(OD-H, 5% IPA in hexanes, 1 mL/min, 220 nm), ee = 97%:
  • 40
  • [ 230299-46-4 ]
  • [ 768-56-9 ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(4-phenylbutan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 41
  • [ 230299-46-4 ]
  • [ 129738-42-7 ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(4-((trans,trans)-4-(p-tolyl)-[1,1'-bi(cyclohexan)]-4-yl)butan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 42
  • [ 230299-46-4 ]
  • [ 112-41-4 ]
  • (+)-(S)-2-(dodecan-2-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 43
  • [ 230299-46-4 ]
  • [ 152715-84-9 ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(5-(trityloxy)pentan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • 44
  • [ 230299-46-4 ]
  • [ 132047-92-8 ]
  • (+)-(S)-tert-butyldiphenyl((4-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)pentyl)oxy)silane [ No CAS ]
  • 45
  • [ 230299-46-4 ]
  • [ 871-90-9 ]
  • (+)-(S)-2-(8-chlorooctan-2-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 46
  • [ 230299-46-4 ]
  • [ 17922-43-9 ]
  • (+)-(S)-methyldiphenyl(2-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)propyl)silane [ No CAS ]
  • 47
  • [ 230299-46-4 ]
  • [ 13142-04-6 ]
  • C21H27BN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.7% With potassium acetate; sodium acetate; In tetrahydrofuran;Reflux; 7-III compound (9.9 g, 32.5 mmol) was added sequentially to the reaction flask.Bis(2,4-dimethyl-2,4-pentanediol) borate (11.3 g, 40.0 mmol), sodium acetate (4.1 g, 50.0 mmol) and tetrahydrofuran (200 mL) were mixed well.Pd(OAc) 2 (0.4 g, 1.6 mmol) was added.Warm to reflux temperature control reaction for 2-3 hours. After TLC detection of the reaction of raw materials was completed, the reaction system was cooled to room temperature, 200 mL of water was added, extraction was performed three times with 200 mL of dichloromethane, 200 mL of saturated saline was washed once, and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure to dryness to obtain crude product 15.2 g, which was recrystallized from acetonitrile and dried to give 9.6 g of 7-I compound in a yield of 80.7%. The purity by HPLC was 98.9%. MS (ESI) m/z: (M+H)=367.2.
  • 48
  • [ 292638-84-7 ]
  • [ 230299-46-4 ]
  • [ 74-88-4 ]
  • (R)-4,4,6,6-tetramethyl-2-(2-phenylpropyl)-1,3,2-dioxaborinane [ No CAS ]
  • 49
  • [ 230299-46-4 ]
  • [ 1120-36-1 ]
  • C28H56B2O4 [ No CAS ]
  • C28H56B2O4 [ No CAS ]
  • 51
  • [ 230299-46-4 ]
  • [ 7321-55-3 ]
  • [ 827-54-3 ]
  • 2-(naphthalen-2-yl)-3-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)propanenitrile [ No CAS ]
  • 52
  • [ 673-32-5 ]
  • [ 230299-46-4 ]
  • [ 7648-30-8 ]
  • C20H27BF2O4 [ No CAS ]
  • 53
  • [ 230299-46-4 ]
  • (R)-1-amino-3-methylbutane-1-boronic acid-1-(2,4-dimethyl-2,4-pentanediol) hydrochloride [ No CAS ]
  • 54
  • [ 230299-46-4 ]
  • C26H37BN4O4 [ No CAS ]
  • 55
  • (R)-2-methyl-N-(3-methylbutylidene)propane-2-sulfinamide [ No CAS ]
  • [ 230299-46-4 ]
  • N-1R-(R-tert-butylsulfinyl)-1-amino-3-methylbutane-1-boronic acid (2,4-dimethyl-2,4-pentanediol) ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With copper(II) sulfate; In pentane; for 18.5h;Inert atmosphere; Large scale; (R)-2-methyl-N-(3-methylbutylidene)propane-2-sulfinamide 1.89 kg (10 mol) was added to a 20 liter reactor, and then 4 liters of n-pentane was added thereto, and the mixture was stirred and dispersed.In a nitrogen-protected atmosphere,Adding (2,4-dimethyl-2,4-pentanediol) bisborate3.38 kg (12 mol), add 221 g of copper sulfate (1 mol) multiple times in 30 minutes.After the addition, the reaction solution was allowed to react at room temperature for 18 hours.TLC monitors the progress of the reaction, after the reaction is completed,2 liters of ethyl acetate dispersion reaction solution was added, and then washed with 3 liters of a 1 N NaHCO 3 aqueous solution, and the upper organic phase was washed three times with saturated brine, and the aqueous phase was separated and discarded.The organic phase was stirred and dried with 200 g of anhydrous sodium sulfate for at least 2 hours.The organic phase is concentrated under reduced pressure to give the compound RN-(R-tert-butylsulfinyl)-1-amino-3-methylbutane-1-boronic acid (2,4-dimethyl-2,4-pentane Alcohol) ester(2.91 kg, yield 88%, de value > 98: 2)
  • 56
  • [ 230299-46-4 ]
  • [ 1333-74-0 ]
  • sodium triethylborohydride [ No CAS ]
  • 4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With (tBuPNN)CoCl2; In tetrahydrofuran; diethyl ether; at 25℃; under 3750.38 Torr; for 20h;Autoclave; In a N2 filled glovebox, complex 1 (1.1 mg, 2.5 umol, 0.05 mol%) was dissolved in 5 mL of Et2O and 1 mL of the resulting solution was added to the reaction vial containing NaBHEt3 (1 uL, 1 M in THF, 1 umol, 0.02 mol%), 6 (1.41 g, 5 mmol) and Et2O (14 mL). The reaction mixture was stirred at 25 C under H2 (5 bar) for 20 h. The borane was purified following the general procedure. Colorless liquid (0.80 g, 56% yield).
  • 57
  • [ 230299-46-4 ]
  • [ 459-64-3 ]
  • 2-(4-methoxyphenyl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 58
  • [ 230299-46-4 ]
  • 1-[4-(methylsulfanyl)phenyl]diazonium tetrafluoroborate [ No CAS ]
  • C14H21BO2S [ No CAS ]
  • 59
  • [ 230299-46-4 ]
  • [ 403-48-5 ]
  • 2-(4-isopropylphenyl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 60
  • [ 230299-46-4 ]
  • [ 673-40-5 ]
  • 2-(4-bromophenyl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 61
  • [ 230299-46-4 ]
  • [ 52436-75-6 ]
  • 2-(4-(tert-butyl)phenyl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • 62
  • [ 230299-46-4 ]
  • 3-(hept-2-yn-1-ylidene)pentane-2,4-dione [ No CAS ]
  • (E)-1-(2-methyl-5-(1-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)pent-1-en-1-yl)furan-3-yl)ethan-1-one [ No CAS ]
  • 63
  • [ 230299-46-4 ]
  • N-tritylpent-4-en-1-amine [ No CAS ]
  • (+)-(S)-4-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-N-tritylpentan-1-amine [ No CAS ]
  • C31H40BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 64
  • [ 230299-46-4 ]
  • [ 152715-84-9 ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(5-(trityloxy)pentan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • C31H39BO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 65
  • [ 230299-46-4 ]
  • [ 132047-92-8 ]
  • (+)-(S)-tert-butyldiphenyl((4-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)pentyl)oxy)silane [ No CAS ]
  • C28H43BO3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 66
  • [ 230299-46-4 ]
  • [ 871-90-9 ]
  • (+)-(S)-2-(8-chlorooctan-2-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • C15H30BClO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 67
  • [ 230299-46-4 ]
  • [ 17922-43-9 ]
  • (+)-(S)-methyldiphenyl(2-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)propyl)silane [ No CAS ]
  • C23H33BO2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 68
  • [ 230299-46-4 ]
  • [ 109790-06-9 ]
  • (+)-(S)-dimethyl(phenyl)(3-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)butyl)silane [ No CAS ]
  • C19H33BO2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 69
  • [ 230299-46-4 ]
  • 1-((hept-6-en-1-yloxy)methyl)-4-(trifluoromethyl)benzene [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-((4-(trifluoromethyl)benzyl)oxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • C22H34BF3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 70
  • [ 230299-46-4 ]
  • 5-((hept-6-en-1-yloxy)methyl)benzo[d][1,3]dioxole [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-(benzo[d][1,3]dioxol-5-ylmethoxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • C22H35BO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 71
  • [ 230299-46-4 ]
  • 1-((hept-6-en-1-yloxy)methyl)-4-(trifluoromethoxy)benzene [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-((4-(trifluoromethoxy)benzyl)oxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • C22H34BF3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 72
  • [ 230299-46-4 ]
  • C18H22O [ No CAS ]
  • C25H37BO3 [ No CAS ]
  • C25H37BO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 73
  • [ 230299-46-4 ]
  • (4-((hept-6-en-1-yloxy)methyl)phenyl)(methyl)sulfane [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-((4-(methylthio)benzyl)oxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • C22H37BO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 74
  • [ 230299-46-4 ]
  • 2-((hept-6-en-1-yloxy)methyl)thiophene [ No CAS ]
  • (+)-(S)-4,4,6,6-tetramethyl-2-(7-(thiophen-2-ylmethoxy)heptan-2-yl)-1,3,2-dioxaborinane [ No CAS ]
  • C19H33BO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 75
  • [ 230299-46-4 ]
  • 2-((hept-6-en-1-yloxy)methyl)furan [ No CAS ]
  • (+)-(S)-2-(7-(furan-2-ylmethoxy)heptan-2-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • C19H33BO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 76
  • [ 230299-46-4 ]
  • C14H18BrClO [ No CAS ]
  • C21H33BBrClO3 [ No CAS ]
  • C21H33BBrClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 77
  • [ 230299-46-4 ]
  • C14H19IO [ No CAS ]
  • C21H34BIO3 [ No CAS ]
  • C21H34BIO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 78
  • [ 230299-46-4 ]
  • 1-(hex-5-en-1-yl)-1H-indole [ No CAS ]
  • (+)-(S)-1-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1H-indole [ No CAS ]
  • C21H32BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 79
  • [ 230299-46-4 ]
  • 1-(hex-5-en-1-yl)-1H-indole-3-carbonitrile [ No CAS ]
  • (+)-(S)-1-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1H-indole-3-carbonitrile [ No CAS ]
  • C22H31BN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 80
  • [ 230299-46-4 ]
  • 1-(hex-5-en-1-yl)-1H-indole-3-carboxylic acid [ No CAS ]
  • C22H32BNO4 [ No CAS ]
  • C22H32BNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 81
  • [ 230299-46-4 ]
  • [ 1334228-85-1 ]
  • (+)-(S)-1-(6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)heptyl)-1H-indole [ No CAS ]
  • C22H34BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 82
  • [ 230299-46-4 ]
  • 9-(hex-5-en-1-yl)-1,2,3,9-tetrahydro-4H-carbazol-4-one [ No CAS ]
  • (+)-(S)-9-(5-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)hexyl)-1,2,3,9-tetrahydro-4Hcarbazol-4-one [ No CAS ]
  • C25H36BNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 83
  • [ 230299-46-4 ]
  • 9-(hept-6-en-1-yl)-9H-carbazole [ No CAS ]
  • (+)-(S)-9-(6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)heptyl)-9H-carbazole [ No CAS ]
  • C26H36BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 84
  • [ 230299-46-4 ]
  • 1-(hept-6-en-1-yl)-1H-pyrrole [ No CAS ]
  • (+)-(S)-1-(6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)heptyl)-1H-pyrrole [ No CAS ]
  • C18H32BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
  • 85
  • [ 230299-46-4 ]
  • C14H18N2 [ No CAS ]
  • C21H33BN2O2 [ No CAS ]
  • C21H33BN2O2 [ No CAS ]
  • C21H33BN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
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