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[ CAS No. 33094-66-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 33094-66-5
Chemical Structure| 33094-66-5
Chemical Structure| 33094-66-5
Structure of 33094-66-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 33094-66-5 ]

CAS No. :33094-66-5 MDL No. :MFCD00459786
Formula : C8H5NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :RSZMTXPFGDUHSE-UHFFFAOYSA-N
M.W : 163.13 Pubchem ID :36328
Synonyms :

Calculated chemistry of [ 33094-66-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.04
TPSA : 58.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 0.19
Consensus Log Po/w : 1.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.146 mg/ml ; 0.000896 mol/l
Class : Soluble
Log S (Ali) : -3.6
Solubility : 0.0408 mg/ml ; 0.00025 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.359 mg/ml ; 0.0022 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.62

Safety of [ 33094-66-5 ]

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

Application In Synthesis of [ 33094-66-5 ]

* 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 [ 33094-66-5 ]

[ 33094-66-5 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 496-41-3 ]
  • [ 33094-66-5 ]
  • [ 64209-68-3 ]
  • [ 10242-12-3 ]
  • 3
  • [ 2120-70-9 ]
  • [ 33094-66-5 ]
  • 4
  • [ 33094-66-5 ]
  • [ 960069-44-7 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 2-nitro-benzofuran In tetrahydrofuran at -25℃; for 1.5h; Stage #2: With water-d2 In tetrahydrofuran at -25 - -10℃; Further stages.;
82% Stage #1: 2-nitro-benzofuran With bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex In tetrahydrofuran at -30℃; Inert atmosphere; Stage #2: With deuteroacetic acid; water-d2 In tetrahydrofuran 2; 3 2-Nitrobenzofuran (4h) (163 mg, 1.00 mmol) in 1.0 ml of dry THF was initially introduced into a dry 25 ml Schlenk flask filled with argon and with a magnetic stirrer core and septum and was cooled to -30° C., and Zn(TMP)2.2LiCl.2MgCl2 dissolved in THF (1.5 ml, 0.37 M, 0.55 equivalent) was added dropwise. After 90 min the metallization was complete (GC analysis of reaction samples to which a solution of I2 in THF had been added indicated a conversion of more than 98%), CH3COOD (10 equiv.) in D2O was slowly added and the mixture was stirred for 10 min. The reaction was ended by addition of saturated NH4Cl solution (10 ml). The aqueous phase was extracted with ethyl acetate (5×10 ml), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by filter column chromatography (silica gel; CH2Cl2); 5h (133 mg, 81%) was obtained as a yellow, crystalline solid.
  • 5
  • [ 33094-66-5 ]
  • [ 1521-51-3 ]
  • [ 960069-48-1 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-nitro-benzofuran With (TMP)2Zn*2MgCl2*2LiCl In tetrahydrofuran at -25℃; for 1.5h; Stage #2: rac-3-bromocyclohexene With CuCN*2LiCl In tetrahydrofuran at -25℃; for 0.5h; Further stages.;
  • 6
  • [ 33094-66-5 ]
  • [ 54125-02-9 ]
  • [ 86-77-1 ]
YieldReaction ConditionsOperation in experiment
80% In benzene at 140℃; for 72h; Cooling with liquid nitrogen; sealed; General Procedure for the thermal reactions of nitrobenzofurans. The temperature, the length of the reaction, and the diene/dienophile ratio were dependent on the starting material and are indicated in [Table 1] and [Table 2]. An ampule containing a solution of 1.0 mmol of the dienophile and the required amount of diene in 0.5 ml of dry benzene was cooled in liquid nitrogen, sealed, and then heated in an oil bath. After the reaction time was completed, it was cooled once more in liquid nitrogen and opened. The solution was evaporated and the residue purified by column chromatography on silica gel or alumina using hexane/ethyl acetate mixtures as eluent.[Table 1] and [Table 2]. An ampule containing a solution of 1.0 mmol of the dienophile and the required amount of diene in 0.5 ml of dry benzene was cooled in liquid nitrogen, sealed, and then heated in an oil bath. After the reaction time was completed, it was cooled once more in liquid nitrogen and opened. The solution was evaporated and the residue purified by column chromatography on silica gel or alumina using hexane/ethyl acetate mixtures as eluent.
  • 7
  • [ 33094-66-5 ]
  • [ 6651-43-0 ]
  • [ 132-64-9 ]
YieldReaction ConditionsOperation in experiment
68% In benzene at 140℃; for 72h; Cooling with liquid nitrogen; sealed; General Procedure for the thermal reactions of nitrobenzofurans. The temperature, the length of the reaction, and the diene/dienophile ratio were dependent on the starting material and are indicated in [Table 1] and [Table 2]. An ampule containing a solution of 1.0 mmol of the dienophile and the required amount of diene in 0.5 ml of dry benzene was cooled in liquid nitrogen, sealed, and then heated in an oil bath. After the reaction time was completed, it was cooled once more in liquid nitrogen and opened. The solution was evaporated and the residue purified by column chromatography on silica gel or alumina using hexane/ethyl acetate mixtures as eluent.[Table 1] and [Table 2]. An ampule containing a solution of 1.0 mmol of the dienophile and the required amount of diene in 0.5 ml of dry benzene was cooled in liquid nitrogen, sealed, and then heated in an oil bath. After the reaction time was completed, it was cooled once more in liquid nitrogen and opened. The solution was evaporated and the residue purified by column chromatography on silica gel or alumina using hexane/ethyl acetate mixtures as eluent.
  • 8
  • [ 33094-66-5 ]
  • 1-dimethylamino-3-tert-butyl(dimethyl)silyloxy-1,3-butadiene [ No CAS ]
  • [ 1251959-00-8 ]
YieldReaction ConditionsOperation in experiment
85% In toluene for 72h; Cooling with liquid nitrogen; sealed; Reflux; General Procedure for the thermal reactions of nitrobenzofurans. The temperature, the length of the reaction, and the diene/dienophile ratio were dependent on the starting material and are indicated in [Table 1] and [Table 2]. An ampule containing a solution of 1.0 mmol of the dienophile and the required amount of diene in 0.5 ml of dry benzene was cooled in liquid nitrogen, sealed, and then heated in an oil bath. After the reaction time was completed, it was cooled once more in liquid nitrogen and opened. The solution was evaporated and the residue purified by column chromatography on silica gel or alumina using hexane/ethyl acetate mixtures as eluent.[Table 1] and [Table 2]. An ampule containing a solution of 1.0 mmol of the dienophile and the required amount of diene in 0.5 ml of dry benzene was cooled in liquid nitrogen, sealed, and then heated in an oil bath. After the reaction time was completed, it was cooled once more in liquid nitrogen and opened. The solution was evaporated and the residue purified by column chromatography on silica gel or alumina using hexane/ethyl acetate mixtures as eluent.
  • 9
  • [ 96853-36-0 ]
  • [ 33094-66-5 ]
YieldReaction ConditionsOperation in experiment
91% With [bis(acetoxy)iodo]benzene; N,N,N-tributyl-1-butanaminium iodide; triethylamine In acetonitrile at 35℃; Inert atmosphere;
76% With [bis(acetoxy)iodo]benzene; N,N,N-tributyl-1-butanaminium iodide; triethylamine In acetonitrile at 35℃; for 0.5h;
98 mg With [bis(acetoxy)iodo]benzene; N,N,N-tributyl-1-butanaminium iodide; triethylamine In acetonitrile at 35℃; for 0.5h;
98 mg With [bis(acetoxy)iodo]benzene; N,N,N-tributyl-1-butanaminium iodide; triethylamine In acetonitrile at 35℃; for 0.5h; Inert atmosphere; Schlenk technique;
With [bis(acetoxy)iodo]benzene; N,N,N-tributyl-1-butanaminium iodide; triethylamine In acetonitrile at 35℃;
With [bis(acetoxy)iodo]benzene; N,N,N-tributyl-1-butanaminium iodide; triethylamine In acetonitrile at 35℃; for 0.5h;
511 mg With [bis(acetoxy)iodo]benzene; N,N,N-tributyl-1-butanaminium iodide; triethylamine In acetonitrile at 35℃; for 0.5h;

  • 10
  • [ 98437-24-2 ]
  • [ 33094-66-5 ]
YieldReaction ConditionsOperation in experiment
78% With bismuth (III) nitrate pentahydrate In benzene at 70 - 80℃; for 2h; Inert atmosphere; General procedure for ipso-nitration of aryl and heteroaryl boronic acids: General procedure: The mixture of aryl boronic acid (50 mg, 1 equiv) and bismuth (III) nitrate (2 equiv) in toluene or benzene (2 mL) was refluxed for 1.5-2 h. Reaction mixture was allowed to cool to room temperature and was filtered through Whatman filter paper. Residue was washed with ethyl acetate followed by DCM. Combined organic layers were evaporated on a rotary evaporator. Crude product was purified by silica gel column chromatography (⋕100-200) using EtOAc/hexane (1:99 to 5:95) as mobile phase.
  • 11
  • [ 90-02-8 ]
  • [ 33094-66-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ammonium acetate; acetic acid / 0.25 h / 90 °C 1.2: 3 h / 135 °C 2.1: sodium tetrahydridoborate / 1,4-dioxane; ethanol / 1 h / 0 °C 3.1: N,N,N-tributyl-1-butanaminium iodide; [bis(acetoxy)iodo]benzene; triethylamine / acetonitrile / 0.5 h / 35 °C
Multi-step reaction with 2 steps 1.1: ammonium acetate; acetic acid / 12 h / 135 °C / Inert atmosphere 2.1: sodium tetrahydridoborate / 1,4-dioxane; ethanol / 1 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 35 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: ammonium acetate; acetic acid / 0.25 h / 90 °C 1.2: 3 h / 135 °C 2.1: sodium tetrahydridoborate / 1,4-dioxane; ethanol / 1 h / 0 °C 3.1: N,N,N-tributyl-1-butanaminium iodide; triethylamine; [bis(acetoxy)iodo]benzene / acetonitrile / 0.5 h / 35 °C
Multi-step reaction with 3 steps 1.1: ammonium acetate; acetic acid / 0.25 h / 90 °C / Inert atmosphere; Schlenk technique 1.2: 3 h / 135 °C / Inert atmosphere; Schlenk technique 2.1: sodium tetrahydridoborate / 1,4-dioxane; ethanol / 1 h / 0 °C / Inert atmosphere; Schlenk technique 3.1: N,N,N-tributyl-1-butanaminium iodide; triethylamine; [bis(acetoxy)iodo]benzene / acetonitrile / 0.5 h / 35 °C / Inert atmosphere; Schlenk technique
Multi-step reaction with 2 steps 1.1: ammonium acetate; acetic acid / 12 h / 90 °C 2.1: sodium tetrahydridoborate / chloroform; isopropanol / 1 h / 0 °C 2.2: 1 h / 20 °C
Multi-step reaction with 3 steps 1.1: ammonium acetate; acetic acid / 0.25 h / 90 °C 1.2: 3 h / 135 °C 2.1: sodium tetrahydridoborate; methanol / 0 - 20 °C 3.1: N,N,N-tributyl-1-butanaminium iodide; triethylamine; [bis(acetoxy)iodo]benzene / acetonitrile / 0.5 h / 35 °C
Multi-step reaction with 3 steps 1.1: acetic acid; ammonium acetate / 0.25 h / 90 °C 1.2: 135 °C 2.1: sodium tetrahydridoborate; ethanol / 1,4-dioxane / 1 h / 0 °C / Inert atmosphere 3.1: triethylamine; [bis(acetoxy)iodo]benzene; N,N,N-tributyl-1-butanaminium iodide / acetonitrile / 0.5 h / 35 °C

  • 12
  • [ 930-22-3 ]
  • [ 33094-66-5 ]
  • C12H11NO4 [ No CAS ]
  • C12H11NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85 % ee With tris-(dibenzylideneacetone)dipalladium(0); C29H21F13NOP; caesium carbonate In toluene at 20℃; for 24h; Inert atmosphere; Sealed tube; Overall yield = 82 %; Overall yield = 38 mg; stereoselective reaction; General procedure for the synthesis of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes 3aa-3fb General procedure: A flame dried sealed tube was cooled to room temperature and filled with argon. To this flask were added Pd2dba3 (9.2 mg, 0.01 mmol, 5 mol %), (S)-L11 (14.9 mg, 11 mol %) and toluene(1 mL). The mixture was stirred at room temperature for 30 min before the addition of 1 (0.2mmol, 1.0 equiv), Cs2CO3 (0.2 mmol, 1.0 equiv), 2 (0.4 mmol, 2.0 equiv) and toluene (1 mL). The reaction was sealed with Teflon plug and stirred at room temperature. After completion (monitored by TLC), the mixture was filtered through celite. The solution was concentrated by rotary evaporation. The diastereomeric ratio was determined by 1H NMR of the crude reaction mixture. Then the residue was purified by silica gel column chromatography (PE/EtOAc =50/1) to afford the desired product 3
  • 13
  • [ 33094-66-5 ]
  • [ 1838-94-4 ]
  • C13H13NO4 [ No CAS ]
  • C13H13NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87 % ee With tris-(dibenzylideneacetone)dipalladium(0); C29H21F13NOP; caesium carbonate In toluene at 20℃; for 24h; Inert atmosphere; Sealed tube; Overall yield = 74 %; Overall yield = 36.7 mg; stereoselective reaction; General procedure for the synthesis of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes 3aa-3fb General procedure: A flame dried sealed tube was cooled to room temperature and filled with argon. To this flask were added Pd2dba3 (9.2 mg, 0.01 mmol, 5 mol %), (S)-L11 (14.9 mg, 11 mol %) and toluene(1 mL). The mixture was stirred at room temperature for 30 min before the addition of 1 (0.2mmol, 1.0 equiv), Cs2CO3 (0.2 mmol, 1.0 equiv), 2 (0.4 mmol, 2.0 equiv) and toluene (1 mL). The reaction was sealed with Teflon plug and stirred at room temperature. After completion (monitored by TLC), the mixture was filtered through celite. The solution was concentrated by rotary evaporation. The diastereomeric ratio was determined by 1H NMR of the crude reaction mixture. Then the residue was purified by silica gel column chromatography (PE/EtOAc =50/1) to afford the desired product 3
  • 14
  • [ 33094-66-5 ]
  • [ 97699-36-0 ]
  • C18H15NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tris-(dibenzylideneacetone)dipalladium(0); C29H21F13NOP; caesium carbonate In toluene at 20℃; for 18h; Inert atmosphere; Sealed tube; stereoselective reaction; General procedure for the synthesis of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes 3aa-3fb General procedure: A flame dried sealed tube was cooled to room temperature and filled with argon. To this flask were added Pd2dba3 (9.2 mg, 0.01 mmol, 5 mol %), (S)-L11 (14.9 mg, 11 mol %) and toluene(1 mL). The mixture was stirred at room temperature for 30 min before the addition of 1 (0.2mmol, 1.0 equiv), Cs2CO3 (0.2 mmol, 1.0 equiv), 2 (0.4 mmol, 2.0 equiv) and toluene (1 mL). The reaction was sealed with Teflon plug and stirred at room temperature. After completion (monitored by TLC), the mixture was filtered through celite. The solution was concentrated by rotary evaporation. The diastereomeric ratio was determined by 1H NMR of the crude reaction mixture. Then the residue was purified by silica gel column chromatography (PE/EtOAc =50/1) to afford the desired product 3
  • 15
  • [ 33094-66-5 ]
  • [ 97699-37-1 ]
  • C18H14FNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tris-(dibenzylideneacetone)dipalladium(0); C29H21F13NOP; caesium carbonate In toluene at 20℃; for 12h; Inert atmosphere; Sealed tube; stereoselective reaction; General procedure for the synthesis of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes 3aa-3fb General procedure: A flame dried sealed tube was cooled to room temperature and filled with argon. To this flask were added Pd2dba3 (9.2 mg, 0.01 mmol, 5 mol %), (S)-L11 (14.9 mg, 11 mol %) and toluene(1 mL). The mixture was stirred at room temperature for 30 min before the addition of 1 (0.2mmol, 1.0 equiv), Cs2CO3 (0.2 mmol, 1.0 equiv), 2 (0.4 mmol, 2.0 equiv) and toluene (1 mL). The reaction was sealed with Teflon plug and stirred at room temperature. After completion (monitored by TLC), the mixture was filtered through celite. The solution was concentrated by rotary evaporation. The diastereomeric ratio was determined by 1H NMR of the crude reaction mixture. Then the residue was purified by silica gel column chromatography (PE/EtOAc =50/1) to afford the desired product 3
  • 16
  • [ 33094-66-5 ]
  • C16H14O [ No CAS ]
  • C24H19NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tris-(dibenzylideneacetone)dipalladium(0); C29H21F13NOP; caesium carbonate In toluene at 20℃; for 20h; Inert atmosphere; Sealed tube; stereoselective reaction; General procedure for the synthesis of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes 3aa-3fb General procedure: A flame dried sealed tube was cooled to room temperature and filled with argon. To this flask were added Pd2dba3 (9.2 mg, 0.01 mmol, 5 mol %), (S)-L11 (14.9 mg, 11 mol %) and toluene(1 mL). The mixture was stirred at room temperature for 30 min before the addition of 1 (0.2mmol, 1.0 equiv), Cs2CO3 (0.2 mmol, 1.0 equiv), 2 (0.4 mmol, 2.0 equiv) and toluene (1 mL). The reaction was sealed with Teflon plug and stirred at room temperature. After completion (monitored by TLC), the mixture was filtered through celite. The solution was concentrated by rotary evaporation. The diastereomeric ratio was determined by 1H NMR of the crude reaction mixture. Then the residue was purified by silica gel column chromatography (PE/EtOAc =50/1) to afford the desired product 3
  • 17
  • [ 33094-66-5 ]
  • C11H12O2 [ No CAS ]
  • C19H17NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris-(dibenzylideneacetone)dipalladium(0); C29H21F13NOP; caesium carbonate In toluene at 20℃; for 24h; Inert atmosphere; Sealed tube; stereoselective reaction; General procedure for the synthesis of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes 3aa-3fb General procedure: A flame dried sealed tube was cooled to room temperature and filled with argon. To this flask were added Pd2dba3 (9.2 mg, 0.01 mmol, 5 mol %), (S)-L11 (14.9 mg, 11 mol %) and toluene(1 mL). The mixture was stirred at room temperature for 30 min before the addition of 1 (0.2mmol, 1.0 equiv), Cs2CO3 (0.2 mmol, 1.0 equiv), 2 (0.4 mmol, 2.0 equiv) and toluene (1 mL). The reaction was sealed with Teflon plug and stirred at room temperature. After completion (monitored by TLC), the mixture was filtered through celite. The solution was concentrated by rotary evaporation. The diastereomeric ratio was determined by 1H NMR of the crude reaction mixture. Then the residue was purified by silica gel column chromatography (PE/EtOAc =50/1) to afford the desired product 3
  • 18
  • [ 33094-66-5 ]
  • [ 6904-16-1 ]
  • 3a-nitro-3-vinyl-3,3a-dihydro-1H-cyclopenta[b]benzofuran-1,1(2H,8bH)-dicarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-bis-(diphenylphosphino)ethane In dichloromethane at 20℃; for 2.5h; Sealed tube; Inert atmosphere; General protocol for the (3+2) cycloaddition reaction (procedure B) General procedure: In a screw-capped vial, vinylcyclopropane (0.44 mmol, 1.1 equiv), 2-nitrobenzofuran(0.40 mmol, 1.0 equiv) and CH2Cl2 (800 μL) were successively added. The resulting mixturewas stirred at room temperature for 5 minutes, before a solution of Pd2(dba)3•CHCl3 (10.4mg, 0.01 mmol, 0.025 equiv) and dppe (8.0 mg, 0.02 mmol, 0.05 equiv) in CH2Cl2 (800 μL),previously stirred at room temperature for 25 minutes, was transferred via cannula. Thecannula was washed with additional CH2Cl2 (400 μL) (total volume of solvent = 2.0 mL) andthe mixture was stirred at room temperature for 2 hours. CH2Cl2 (10 mL) was then added,and the mixture was loaded onto a small silica plug, eluted with additional CH2Cl2 (40 mL)and concentrated under reduced pressure. After measurement of the diastereomeric ratioby 1H NMR, the resulting crude mixture was purified by flash column chromatography toafford the desired cycloadduct.When a clear distinction between the two diastereomers cannot be observed in NMR, thecombined analytical data for both isomers are reported.
  • 19
  • [ 33094-66-5 ]
  • C20H25NO6 [ No CAS ]
  • (1S,3aR,8bS)-ethyl 1'-ethyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 56h; stereoselective reaction;
  • 20
  • [ 33094-66-5 ]
  • ethyl 2-(1-benzyl-3-((tert-butoxycarbonyl)oxy)-2-oxoindolin-3-yl)acrylate [ No CAS ]
  • (1S,3aR,8bS)-ethyl 1'-benzyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 56h; stereoselective reaction;
  • 21
  • [ 33094-66-5 ]
  • C20H25NO6 [ No CAS ]
  • (1S,3aR,8bS)-ethyl 1',5'-dimethyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 48h; stereoselective reaction;
  • 22
  • [ 33094-66-5 ]
  • C20H25NO7 [ No CAS ]
  • (1S,3aR,8bS)-ethyl 5'-methoxy-1'-methyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 50h; stereoselective reaction;
  • 23
  • [ 33094-66-5 ]
  • C19H22FNO6 [ No CAS ]
  • (1S,3aR,8bS)-ethyl 5'-fluoro-1'-methyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 53h; stereoselective reaction;
  • 24
  • [ 33094-66-5 ]
  • C19H22FNO6 [ No CAS ]
  • (1S,3aR,8bS)-ethyl 7'-fluoro-1'-methyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 53h; stereoselective reaction;
  • 25
  • [ 33094-66-5 ]
  • C19H22ClNO6 [ No CAS ]
  • (1S,3aR,8bS)-ethyl 5'-chloro-1'-methyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 48h; stereoselective reaction;
  • 26
  • [ 33094-66-5 ]
  • C19H22ClNO6 [ No CAS ]
  • (1S,3aR,8bS)-ethyl 6'-chloro-1'-methyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 55h; stereoselective reaction;
  • 27
  • [ 33094-66-5 ]
  • C19H22BrNO6 [ No CAS ]
  • (1S,3aR,8bS)-ethyl 5'-bromo-1'-methyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 50h; stereoselective reaction;
  • 28
  • [ 33094-66-5 ]
  • [ 1321139-49-4 ]
  • (1S,3aR,8bS)-methyl 1'-methyl-3a-nitro-2'-oxo-3a,8b-dihydrospiro[cyclopenta[b]benzofuran-1,3'-indoline]-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With 6'-phenyl-β-isocupreidine In chloroform at 0℃; for 48h; stereoselective reaction;
  • 29
  • [ 33094-66-5 ]
  • 2-tosylaminochalcone [ No CAS ]
  • 2-((5aS,10aS,11S)-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)-1-phenylethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: 2-tosylaminochalcone In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 30
  • [ 33094-66-5 ]
  • C23H21NO3S [ No CAS ]
  • 2-((5aS,10aS,11S)-2-methyl-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)-1-phenylethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C23H21NO3S In dichloromethane at 20℃; for 72h; stereoselective reaction;
  • 31
  • [ 33094-66-5 ]
  • C22H18ClNO3S [ No CAS ]
  • 2-((5aS,10aS,11S)-2-chloro-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)-1-phenylethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C22H18ClNO3S In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 32
  • [ 33094-66-5 ]
  • C22H18BrNO3S [ No CAS ]
  • 2-((5aS,10aS,11S)-2-bromo-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)-1-phenylethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C22H18BrNO3S In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 33
  • [ 33094-66-5 ]
  • C22H18FNO3S [ No CAS ]
  • 1-(4-fluorophenyl)-2-((5aS,10aS,11S)-10a-nitro-5-tosyl5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)ethan-1one [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C22H18FNO3S In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 34
  • [ 33094-66-5 ]
  • C22H17Cl2NO3S [ No CAS ]
  • 1-(3,4-dichlorophenyl)-2-((5aS,10aS,11S)-10a-nitro-5-tosyl5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)ethan-1one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C22H17Cl2NO3S In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 35
  • [ 33094-66-5 ]
  • C23H21NO3S [ No CAS ]
  • 2-((5aS,10aS,11S)-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)-1-(o-tolyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C23H21NO3S In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 36
  • [ 33094-66-5 ]
  • C23H21NO3S [ No CAS ]
  • 2-((5aS,10aS,11S)-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)-1-(p-tolyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C23H21NO3S In dichloromethane at 20℃; for 72h; stereoselective reaction;
  • 37
  • [ 33094-66-5 ]
  • C23H21NO4S [ No CAS ]
  • 1-(3-methoxyphenyl)-2-((5aS,10aS,11S)-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)ethan-1one [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C23H21NO4S In dichloromethane at 20℃; for 72h; stereoselective reaction;
  • 38
  • [ 33094-66-5 ]
  • C23H21NO4S [ No CAS ]
  • 1-(4-methoxyphenyl)-2-((5aS,10aS,11S)-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)ethan-1one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C23H21NO4S In dichloromethane at 20℃; for 72h; stereoselective reaction;
  • 39
  • [ 33094-66-5 ]
  • C20H17NO4S [ No CAS ]
  • 1-(furan-2-yl)-2-((5aS,10aS,11S)-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C20H17NO4S In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 40
  • [ 33094-66-5 ]
  • C20H17NO3S2 [ No CAS ]
  • 2-((5aS,10aS,11S)-10a-nitro-5-tosyl-5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)-1-(thiophen-2-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C20H17NO3S2 In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 41
  • [ 33094-66-5 ]
  • C26H21NO3S [ No CAS ]
  • 1-(naphthalen-2-yl)-2-((5aS,10aS,11S)-10a-nitro-5-tosyl5,5a,10a,11-tetrahydrobenzofuro[3,2-b]quinolin-11-yl)ethan-1one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 2-nitro-benzofuran With C23H24F6N2O2 In dichloromethane at 20℃; for 0.166667h; Stage #2: C26H21NO3S In dichloromethane at 20℃; for 48h; stereoselective reaction;
  • 42
  • [ 3156-43-2 ]
  • [ 33094-66-5 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 2-(2-nitro-vinyl)-phenol With sodium tetrahydroborate In chloroform; isopropyl alcohol at 0℃; for 1h; Stage #2: With [bis(acetoxy)iodo]benzene; tetra-(n-butyl)ammonium iodide; triethylamine In chloroform; isopropyl alcohol; acetonitrile at 20℃; for 1h;
Stage #1: 2-(2-nitro-vinyl)-phenol With sodium tetrahydroborate In 1,4-dioxane; ethanol at 0℃; for 1h; Inert atmosphere; Stage #2: With [bis(acetoxy)iodo]benzene; tetra-(n-butyl)ammonium iodide; triethylamine In acetonitrile at 35℃; for 0.5h; Inert atmosphere;
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / 1,4-dioxane; ethanol / 1 h / 0 °C 2: tetra-(n-butyl)ammonium iodide; triethylamine; [bis(acetoxy)iodo]benzene / acetonitrile / 0.5 h / 35 °C
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0 - 20 °C 2: tetra-(n-butyl)ammonium iodide; triethylamine; [bis(acetoxy)iodo]benzene / acetonitrile / 35 °C
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 0 - 20 °C 2: tetra-(n-butyl)ammonium iodide; triethylamine; [bis(acetoxy)iodo]benzene / acetonitrile / 0.5 h / 35 °C

  • 43
  • [ 33094-66-5 ]
  • [ 14369-81-4 ]
  • ethyl 3a-nitro-3a,8b-dihydro-3H-cyclopenta[b]benzofuran-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With diphenyl(methyl)phosphine In dichloromethane at 0℃; for 8h;
75% With triphenylphosphine In benzene at 20℃; Inert atmosphere; Schlenk technique; diastereoselective reaction; 7. General procedure for dearomative [3+2] annulation of 2-nitrobenzofuran 1w 2-nitrobenzothiophene 1x General procedure: Under nitrogen atmosphere, the reaction tube was charged with 2-nitrobenzofuran 1w (0.2 mmol) or 2-nitrobenzothiophene 1x (0.2 mmol), triphenylphosphine (10.6 mg, 0.04 mmol) and benzene (2.0 mL). Then the ethyl 2,3-Butadienoate 2a (36.0 uL, 0.3 mmol) was added and the mixture was stirred at room temperature. After completion of the reaction (TLC), the mixture was treated with water (10 mL) and additional stirring for 5 minutes, the aqueous phase was extracted with ethyl acetate (3 x 10 mL). The combined organic extracts were washed with an aqueous saturated solution of sodium chloride, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash column chromatography (Petroleum ether/ethyl acetate) to afford the desired product. Ethyl 3a-nitro-3a,8b-dihydro-3H-cyclopenta[b]benzofuran-1-carboxylate (3wa): the reaction was conducted at 0.2 mmol scale, 41.4 mg, 75% yield, unknown compound, yellow oil, Rf = 0.25 (petroleum ether/ethyl acetate 30/1). 1H NMR (400 MHz, CDCl3) δ 7.49 (d, J = 7.6 Hz, 1H), 7.17 (t, J = 7.6 Hz, 1H), 6.96-6.90 (m, 2H), 6.67 (d, J = 2.2 Hz, 1H), 5.04 (s, 1H), 4.18 (q, J = 7.1 Hz, 2H), 3.65 (d, J = 19.6 Hz, 1H), 3.24 (d, J = 19.6 Hz, 1H), 1.26 (t, J = 7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 162.8, 158.0, 138.9, 135.2, 129.8, 126.7, 124.1, 123.2, 121.7, 110.5, 61.3, 60.7, 44.4, 14.4. HRMS (EI) m/z Calculated for C14H13NO5 [M]+ 275.0794, found 275.0802.
  • 44
  • [ 33094-66-5 ]
  • [ 1187847-13-7 ]
  • methyl (1R,3aR,8bR)-3a-nitro-1-(p-tolyl)-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With (R)-SITCP In chloroform at 0℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;
92% With (R)-SITCP In chloroform at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; 2 Example 2 To a 10 mL Schlenk tube was added 2-nitrobenzofuran 1a (16.3 mg, 0.1 mmol).MBH carbonate 2d (61.2mg, 0.2mmol)And C6 (3.6 mg, 0.01 mmol).The tube was sealed with a threaded rubber stopper and replaced with nitrogen three times.CHCl3 (1.0 mL) was then added via syringe.The mixture was stirred at 0 ° C for 12 hours.The reaction was followed by TLC, after the reaction was completed,The reaction mixture was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1/15 by volume).32.3 mg of light yellow solid product 3ad was obtained.Yield 92%,Dr value > 20/1, 94% ee.
  • 45
  • [ 33094-66-5 ]
  • [ 1132641-31-6 ]
  • methyl (1R,3aR,8bR)-1-(4-fluorophenyl)-3a-nitro-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With (R)-SITCP In chloroform at 0℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;
87% With (R)-SITCP In chloroform at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; 3 Example 3 To a 10 mL Schlenk tube was added 2-nitrobenzofuran 1a (16.3 mg, 0.1 mmol).MBH carbonate 2e (62.0 mg, 0.2 mmol)And C6 (3.6 mg, 0.01 mmol).The tube was sealed with a threaded rubber stopper and replaced with nitrogen three times.CHCl3 (1.0 mL) was then added via syringe.The mixture was stirred at 0 ° C for 12 hours.The reaction was followed by TLC, after the reaction was completed,The reaction mixture was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1/15 by volume).30.9 mg of light yellow solid product 3ae was obtained.Yield 87%,Dr value > 20/1, 94% ee.
  • 46
  • [ 33094-66-5 ]
  • [ 1279575-38-0 ]
  • methyl (1R,3aR,8bR)-1-(4-cyanophenyl)-3a-nitro-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With (R)-SITCP In chloroform at 0℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;
86% With (R)-SITCP In chloroform at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; 4 Example 4 To a 10 mL Schlenk tube was added 2-nitrobenzofuran 1a (16.3 mg, 0.1 mmol).MBH carbonate 2h (63.4mg, 0.2mmol)And C6 (3.6 mg, 0.01 mmol).The tube was sealed with a threaded rubber stopper and replaced with nitrogen three times.CHCl3 (1.0 mL) was then added via syringe.The mixture was stirred at 0 ° C for 12 hours.The reaction was followed by TLC, after the reaction was completed,The reaction mixture was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1/5 by volume).31.2 mg of white solid product 3ah was obtained.Yield 86%,Dr value > 20/1, 96% ee.
  • 47
  • [ 33094-66-5 ]
  • [ 688012-87-5 ]
  • methyl (1R,3aR,8bR)-3a-nitro-1-(4-nitrophenyl)-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With (R)-SITCP In chloroform at 0℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;
85% With (R)-SITCP In chloroform at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; 5 Example 5 To a 10 mL Schlenk tube was added 2-nitrobenzofuran 1a (16.3 mg, 0.1 mmol).MBH carbonate 2i (67.4 mg, 0.2 mmol)And C6 (3.6 mg, 0.01 mmol).The tube was sealed with a threaded rubber stopper and replaced with nitrogen three times.CHCl3 (1.0 mL) was then added via syringe.The mixture was stirred at 0 ° C for 12 hours.The reaction was followed by TLC, after the reaction was completed,The reaction mixture was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1/5 by volume).32.5 mg of white solid product 3ai was obtained.Yield 85%,Dr value > 20/1, 96% ee.
  • 48
  • [ 33094-66-5 ]
  • [ 1132641-30-5 ]
  • methyl (1S,3aR,8bR)-1-(2-chlorophenyl)-3a-nitro-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With (R)-SITCP In chloroform at 0℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;
88% With (R)-SITCP In chloroform at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; 6 Example 6 To a 10 mL Schlenk tube was added 2-nitrobenzofuran 1a (16.3 mg, 0.1 mmol).MBH carbonate 2j (65.2 mg, 0.2 mmol)And C6 (3.6 mg, 0.01 mmol).The tube was sealed with a threaded rubber stopper and replaced with nitrogen three times.CHCl3 (1.0 mL) was then added via syringe.The mixture was stirred at 0 ° C for 12 hours.The reaction was followed by TLC, after the reaction was completed,The reaction mixture was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1/15 by volume).32.6 mg of white solid product 3aj was obtained.Yield 88%,Dr value > 20/1, 96% ee.
  • 49
  • [ 33094-66-5 ]
  • [ 1132641-33-8 ]
  • methyl (1R,3aR,8bR)-1-(3,4-dichlorophenyl)-3a-nitro-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With (R)-SITCP In chloroform at 0℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;
90% With (R)-SITCP In chloroform at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; 7 Example 7 To a 10 mL Schlenk tube was added 2-nitrobenzofuran 1a (16.3 mg, 0.1 mmol).MBH carbonate 2l (72.0 mg, 0.2 mmol)And C6 (3.6 mg, 0.01 mmol).The tube was sealed with a threaded rubber stopper and replaced with nitrogen three times.CHCl3 (1.0 mL) was then added via syringe.The mixture was stirred at 0 ° C for 12 hours.The reaction was followed by TLC. After the reaction was completed, the reaction mixture was purified by preparative thin layer chromatography using ethyl acetate/petrole ether (1/15 by volume).36.4 mg of light yellow solid product 3al were obtained.Yield 90%,Dr value > 20/1, 96% ee.
  • 50
  • [ 33094-66-5 ]
  • [ 1265015-72-2 ]
  • tert-butyl (3aR,8bR)-3a-nitro-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With (R)-SITCP In chloroform at 0℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;
94% With (R)-SITCP In chloroform at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; 8 Example 8 To a 10 mL Schlenk tube was added 2-nitrobenzofuran 1a (16.3 mg, 0.1 mmol).MBH carbonate 2o (51.6mg, 0.2mmol)And C6 (3.6 mg, 0.01 mmol).The tube was sealed with a threaded rubber stopper and replaced with nitrogen three times.CHCl3 (1.0 mL) was then added via syringe.The mixture was stirred at 0 ° C for 12 hours.The reaction was followed by TLC, after the reaction was completed,The reaction mixture was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1/15 by volume).28.4 mg of white solid product 3ao were obtained.Yield 94%,Dr value > 20/1, 96% ee.
  • 51
  • [ 33094-66-5 ]
  • ethyl 2-((tert-butoxycarbonyloxy)(phenyl)methyl)acrylate [ No CAS ]
  • ethyl (1R,3aR,8bR)-3a-nitro-1-phenyl-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With (R)-SITCP In chloroform at 0℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;
93% With (R)-SITCP In chloroform at 0℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; 1; 15 Investigation of reaction conditions (taking entry 12 as an example) To a 10 mL Schlenk tube was added 2-nitrobenzofuran 1a (16.3 mg, 0.1 mmol).MBH carbonate 2a (61.2 mg, 0.2 mmol)And C6 (3.6 mg, 0.01 mmol).The tube was sealed with a threaded rubber stopper, replaced with nitrogen three times, and then CHCl3 (1.0 mL) was added by a syringe.The mixture was stirred at 0 ° C for 12 hours.The reaction was followed by TLC, after the reaction was completed,The reaction mixture was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1/15 by volume).32.6 mg of white solid product 3aa was obtained.Yield 93%,Dr value > 20/1, 97% ee.
  • 52
  • [ 33094-66-5 ]
  • [ 2510-03-4 ]
  • 6-amino-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With cetyltrimethylammonim bromide In water at 20℃; for 24h; 1; 1-6 Example 1 Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90%
90% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. 4.2.1. 6-Amino-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile (3aa) White solid; 27.9 mg, 90% yield; mp 182.3-183.1 °C; 1H NMR(300 MHz, DMSO-d6) δ 8.20 (d, J = 7.7 Hz, 1H), 8.07 (d, J = 7.5 Hz, 1H), 7.75 (d, J = 8.3 Hz, 1H), 7.60 (t, J = 7.8 Hz, 1H), 7.49-7.41 (m,1H), 7.41-7.29 (m, 3H), 6.36 (s, 2H), 3.17-3.06 (m, 2H), 2.89-2.78 (m,2H); 13C NMR (75 MHz, DMSO-d6) δ 156.2, 142.0, 138.5, 138.0, 132.1,131.2, 128.5, 127.9, 127.9, 126.6, 126.1, 124.8, 123.7, 123.6, 123.5, 121.8,118.7, 112.1, 88.6, 28.5, 24.3; HRMS (ESI-TOF) calcd. for C21H15N2O [M + H]+ 311.1179; found: 311.1170.
  • 53
  • [ 33094-66-5 ]
  • C14H17NO3 [ No CAS ]
  • ethyl (R)-3-((2S,3R)-2-nitro-2,3-dihydrobenzofuran-3-yl)-2-oxo-3-propylindoline-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With C37H35F6N5OS In 5,5-dimethyl-1,3-cyclohexadiene at -20℃; for 12h; stereoselective reaction;
  • 54
  • [ 33094-66-5 ]
  • [ 16176-42-4 ]
  • (S)-1-methyl-3-((2S,3R)-2-nitro-2,3-dihydrobenzofuran-3-yl)-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With C37H35F6N5OS In 5,5-dimethyl-1,3-cyclohexadiene at -20℃; for 40h; stereoselective reaction;
  • 55
  • [ 33094-66-5 ]
  • C13H11FN2O [ No CAS ]
  • (S)-5-fluoro-1-methyl-3-((2S,3R)-2-nitro-2,3-dihydrobenzofuran-3-yl)-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With C37H35F6N5OS In 5,5-dimethyl-1,3-cyclohexadiene at -20℃; for 40h; stereoselective reaction;
  • 56
  • [ 33094-66-5 ]
  • 5-chloro-1-methyl-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
  • (S)-5-chloro-1-methyl-3-((2S,3R)-2-nitro-2,3-dihydrobenzofuran-3-yl)-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With C37H35F6N5OS In 5,5-dimethyl-1,3-cyclohexadiene at -20℃; for 40h; stereoselective reaction;
  • 57
  • [ 33094-66-5 ]
  • 6-chloro-1-methyl-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
  • (S)-6-chloro-1-methyl-3-((2S,3R)-2-nitro-2,3-dihydrobenzofuran-3-yl)-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With C37H35F6N5OS In 5,5-dimethyl-1,3-cyclohexadiene at -20℃; for 45h; stereoselective reaction;
  • 58
  • [ 33094-66-5 ]
  • C13H11ClN2O [ No CAS ]
  • (S)-7-chloro-1-methyl-3-((2S,3R)-2-nitro-2,3-dihydrobenzofuran-3-yl)-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With C37H35F6N5OS In 5,5-dimethyl-1,3-cyclohexadiene at -20℃; for 40h; stereoselective reaction;
  • 59
  • C12H8N2O(CH3Br) [ No CAS ]
  • [ 33094-66-5 ]
  • (S)-5-bromo-1-methyl-3-((2S,3R)-2-nitro-2,3-dihydrobenzofuran-3-yl)-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With C37H35F6N5OS In 5,5-dimethyl-1,3-cyclohexadiene at -20℃; for 40h; stereoselective reaction;
  • 60
  • [ 33094-66-5 ]
  • [ 16176-43-5 ]
  • (S)-1,5-dimethyl-3-((2S,3R)-2-nitro-2,3-dihydrobenzofuran-3-yl)-3-(1H-pyrrol-1-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With C37H35F6N5OS In 5,5-dimethyl-1,3-cyclohexadiene at -20℃; for 66h; stereoselective reaction;
  • 61
  • [ 33094-66-5 ]
  • [ 2972-85-2 ]
  • 4-amino-2-(4-methoxyphenyl)dibenzo[b,d]furan-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 62
  • [ 33094-66-5 ]
  • [ 62737-71-7 ]
  • 4-amino-2-(furan-2-yl)dibenzo[b,d]furan-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 63
  • [ 33094-66-5 ]
  • [ 10432-43-6 ]
  • 4-amino-2-(naphthalen-2-yl)dibenzo[b,d]furan-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 64
  • [ 33094-66-5 ]
  • 2-(6-fluoro-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]
  • 6-amino-2-fluoro-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 65
  • [ 33094-66-5 ]
  • [ 17516-01-7 ]
  • 6-amino-2-methoxy-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 66
  • [ 33094-66-5 ]
  • [ 17515-99-0 ]
  • 6-amino-3-methyl-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 67
  • [ 33094-66-5 ]
  • 2-(6,7-dimethyl-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]
  • 6-amino-2,3-dimethyl-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 68
  • [ 875433-62-8 ]
  • [ 33094-66-5 ]
  • 6-amino-2,3-dimethoxy-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 69
  • [ 33094-66-5 ]
  • [ 30197-78-5 ]
  • C20H12N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 70
  • [ 2510-01-2 ]
  • [ 33094-66-5 ]
  • 6-amino-12H-fluoreno[2,1-b]benzofuran-7-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 71
  • [ 33094-66-5 ]
  • [ 14003-22-6 ]
  • 6-amino-13,14-dihydro-12H-benzo[b]benzo[3,4]cyclohepta[1,2-e]benzofuran-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 72
  • [ 33094-66-5 ]
  • [ 5447-87-0 ]
  • 4-amino-2-phenyldibenzo[b,d]furan-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 73
  • [ 33094-66-5 ]
  • [ 579-48-6 ]
  • 4-amino-2-(4-fluorophenyl)dibenzo[b,d]furan-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 74
  • [ 33094-66-5 ]
  • [ 26088-78-8 ]
  • 4-amino-2-(4-bromophenyl)dibenzo[b,d]furan-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 75
  • [ 33094-66-5 ]
  • [ 3111-61-3 ]
  • 4-amino-2-(p-tolyl)dibenzo[b,d]furan-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h; 4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
  • 76
  • [ 33094-66-5 ]
  • [ 135365-28-5 ]
  • C20H18N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With C40H46F6N2OPS(1+)*Br(1-); potassium carbonate In diethyl ether at 20℃; for 24h; General procedure for asymmetric synthesis of tropane derivatives. General procedure: To a round bottle flask with a magnetic stirring bar were added methyl 1-methyl-3,4-dihydroisoquinoline-3-carboxylate 1 (0.12 mmol) and 2-nitrobenzofuran 2(0.10 mmol), followed by the addition of K2CO3 (0.2 mmol) and catalyst P11 (5 mol%), then followed by the addition of Et2O (2.0 mL). The reaction mixture was stirred at rt for 24 h, and thin layer chromatography (TLC) showed that the reaction was completed. Then, the residue was purified by column chromatography on silica gel to afford 3/4.
94% With C48H62F6N2OPS(1+)*Br(1-); potassium hydroxide In diethyl ether at 20℃; for 24h; 1.2 (2) Synthesis of the target compound 3a of the present invention In the round-bottomed flask was added raw material 1a (24.4mg, 0.12mmol), and then added raw material 2a (0.1mmol, 19.3mg); then added KOH (0.2mmol, 27.6mg), catalyst P11 (5mol%, 4.1mg), and then Solvent ether (1 mL) was added and reacted at room temperature for 24 hours. TLC monitored the reaction to complete, and was directly separated by silica gel column chromatography to obtain the target product 3a, white powder, 34.4 mg, yield 94%, ee 92%.
  • 77
  • [ 33094-66-5 ]
  • [ 65131-08-0 ]
  • [ 479-11-8 ]
YieldReaction ConditionsOperation in experiment
81% With caesium carbonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; 4.1.3 Annulation of sulfonyl phthalide with 2-nitrobenzofurans towards naphthoquinones General procedure: General procedure for the synthesis of annulated quinones. To a stirred solution of 3-sulfonyl phthalide 75 (0.2mmol, 54mg, 1.0 equiv) and 2-nitrobenzofurans 88-93 (0.2mmol, 1.0 equiv) in THF (5.0mL) was added Cs2CO3 (0.2mmol, 66mg, 1.0 equiv) at room temperature until completion of the reaction (overnight, 12h, monitored by TLC). The solvent was evaporated in vacuo. The residue was then subjected to silica gel column chromatography by gradient elution with ethyl acetate/hexane (2:98) affording the respective quinones 94-99. Naphtho[2,3-b]benzofuran-6,11-dione (94). Yellow solid; Yield 40mg, 81%, mp 231-233°C; IR (neat, cm-1 3077 (vw), 2915 (vw), 2847 (vw), 1660 (br vs), 1563 (m), 1486 (w), 1223 (m), 1179 (m), 987 (m), 747 (s), 713 (s); 1H NMR (500MHz, CDCl3) δ 7.50 (t, J=7.8Hz, 1H), 7.59 (t, J=7.8Hz, 1H), 7.70 (d, J=7.8Hz, 1H), 7.75-7.84 (m, 2H), 8.20-8.28 (m, 2H), 8.31 (d, J=7.8Hz, 1H); 13C NMR (125MHz, CDCl3) δ 113.1, 122.9, 124.2, 126.3, 127.0, 127.1, 129.8, 132.5, 133.5, 134.1, 134.4, 153.7, 156.6, 175.7, 181.6; HRMS (ES+) calcd for C16H9O3 (MH+) 249.0544, found 249.0546.
  • 78
  • [ 33094-66-5 ]
  • 1-allyl-3-((2,2,2-trifluoroethyl)imino)indolin-2-one [ No CAS ]
  • (1R,3S,3aS,8bS)-1'-allyl-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
  • C21H16F3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88 % ee With C32H28F6N4O3 In chloroform at 20℃; for 48h; Sealed tube; Overall yield = 90 percent; Overall yield = 19.4 mg; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
  • 79
  • [ 33094-66-5 ]
  • 1-benzyl-3-((2,2,2-trifluoroethyl)imino)indolin-2-one [ No CAS ]
  • (1S,3R,3aR,8bR)-1'-benzyl-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro(benzofuro[2,3-c]pyrrole-3,3'-indolin)-2'-one [ No CAS ]
  • (1R,3S,3aS,8bS)-1'-benzyl-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 % ee With C32H28F6N4O3 In chloroform at 20℃; Sealed tube; Overall yield = 92 percent; Overall yield = 22.1 mg; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
54 % ee With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(pyrrolidin-1-yl)cyclohexyl)thiourea In dichloromethane at 0℃; for 24h; Molecular sieve; Overall yield = 85 percent;
  • 80
  • [ 33094-66-5 ]
  • 3-((2,2,2-trifluoroethyl)imino)indolin-2-one [ No CAS ]
  • (1R,3S,3aS,8bS)-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With C32H28F6N4O3 In chloroform at 20℃; for 96h; Sealed tube; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
68% With 2-(((S)-2-(hydroxydiphenylmethyl)azetidin-1-yl)methyl)-6-(((S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)-4-methylphenol; diethylzinc In hexane; toluene at 25℃; for 48h; Schlenk technique; Inert atmosphere; Molecular sieve; stereoselective reaction;
  • 81
  • [ 33094-66-5 ]
  • C11H9F3N2O2 [ No CAS ]
  • (1R,3S,3aS,8bS)-5'-methoxy-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With C32H28F6N4O3 In chloroform at 20℃; for 48h; Sealed tube; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
63% With 2-(((S)-2-(hydroxydiphenylmethyl)azetidin-1-yl)methyl)-6-(((S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)-4-methylphenol; diethylzinc In hexane; toluene at 25℃; for 48h; Schlenk technique; Inert atmosphere; Molecular sieve; stereoselective reaction;
  • 82
  • [ 33094-66-5 ]
  • C11H9F3N2O [ No CAS ]
  • (1R,3S,3aS,8bS)-5'-methyl-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With C32H28F6N4O3 In chloroform at 20℃; for 48h; Sealed tube; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
67% With 2-(((S)-2-(hydroxydiphenylmethyl)azetidin-1-yl)methyl)-6-(((S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)-4-methylphenol; diethylzinc In hexane; toluene at 25℃; for 48h; Schlenk technique; Inert atmosphere; Molecular sieve; stereoselective reaction;
  • 83
  • [ 33094-66-5 ]
  • C10H6BrF3N2O [ No CAS ]
  • (1R,3S,3aS,8bS)-5'-bromo-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With C32H28F6N4O3 In chloroform at 20℃; for 48h; Sealed tube; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
53% With 2-(((S)-2-(hydroxydiphenylmethyl)azetidin-1-yl)methyl)-6-(((S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)-4-methylphenol; diethylzinc In hexane; toluene at 25℃; for 48h; Schlenk technique; Inert atmosphere; Molecular sieve; stereoselective reaction;
  • 84
  • [ 33094-66-5 ]
  • C10H6ClF3N2O [ No CAS ]
  • (1R,3S,3aS,8bS)-5'-chloro-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With C32H28F6N4O3 In chloroform at 20℃; for 96h; Sealed tube; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
62% With 2-(((S)-2-(hydroxydiphenylmethyl)azetidin-1-yl)methyl)-6-(((S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)-4-methylphenol; diethylzinc In hexane; toluene at 25℃; for 48h; Schlenk technique; Inert atmosphere; Molecular sieve; stereoselective reaction;
  • 85
  • [ 33094-66-5 ]
  • C10H6ClF3N2O [ No CAS ]
  • (1R,3S,3aS,8bS)-7'-chloro-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
  • C18H11ClF3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88 % ee With C32H28F6N4O3 In chloroform at 20℃; for 96h; Sealed tube; Overall yield = 83 percent; Overall yield = 17.6 mg; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
  • 86
  • [ 33094-66-5 ]
  • C10H6F3N3O3 [ No CAS ]
  • (1R,3S,3aS,8bS)-3a,5'-dinitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With C32H28F6N4O3 In chloroform at 20℃; for 96h; Sealed tube; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
  • 87
  • [ 33094-66-5 ]
  • C10H5Br2F3N2O [ No CAS ]
  • (1R,3S,3aS,8bS)-5',7'-dibromo-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
  • C18H10Br2F3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.778 % ee With C32H28F6N4O3 In chloroform at 20℃; for 96h; Sealed tube; Overall yield = 76 percent; Overall yield = 16.5 mg; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
  • 88
  • [ 33094-66-5 ]
  • 1-methyl-3-((2,2,2-trifluoroethyl)- imino)indolin-2-one [ No CAS ]
  • (1R,3S,3aS,8bS)-1'-methyl-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With C32H28F6N4O3 In chloroform at 20℃; for 48h; Sealed tube; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
  • 89
  • [ 33094-66-5 ]
  • 1-methyl-3-((2,2,2-trifluoroethyl)- imino)indolin-2-one [ No CAS ]
  • (1R,3S,3aS,8bS)-1'-methyl-3a-nitro-1-(trifluoromethyl)-1,2,3a,8b-tetrahydrospiro[benzofuro[2,3-c]pyrrole-3,3'-indolin]-2'-one [ No CAS ]
  • C19H14F3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With C32H28F6N4O3 In dichloromethane at 20℃; for 48h; Sealed tube; stereoselective reaction; 2. Organocatalytic synthesis of 3 - general procedure General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screwcap, the corresponding nitro-substituted benzoheteroarene 1 (1.0 equiv., 0.05 mmol), catalyst4h (0.2 equiv., 0.02 mmol, 6.3 mg) and the corresponding imine 2 (1.5 equiv., 0.075 mmol)were dissolved in CHCl3 (0.1 mL). The reaction mixture was stirred for indicated time atambient temperature. After full conversion of the starting material 1 (as confirmed by 1H NMRof a crude reaction mixture), the reaction mixture was directly subjected to flashchromatography on silica gel to obtain pure products 3.The racemic samples of products 3 for chiral UPC2 separation studies were prepared usingequimolar mixture of quinine and quinidine as catalyst.
  • 90
  • [ 33094-66-5 ]
  • [ 84066-68-2 ]
  • (3aS,8aR)-2-(4-methoxyphenyl)-3-((E)-styryl)-3a,8a-dihydrofuro[2,3-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With (4S,7R,8S)-4-((R)-1-((tert-butyldiphenylsilyl)oxy)ethyl)-1-(3,5-dimethoxyphenyl)-8,11,11-trimethyl-6-oxo-7-(perfluorobenzamido)-2,2,10,10-tetraphenyl-9-oxa-5-aza-2-phospha-10-siladodecan-2-ium bromide; sodium hydrogencarbonate In hexane at 20℃; for 48h; stereoselective reaction;
  • 91
  • [ 33094-66-5 ]
  • (E)-1-phenyl-4-(m-tolyl)but-3-en-1-one [ No CAS ]
  • (3aS,8aR)-3-((E)-3-methylstyryl)-2-phenyl-3a,8a-dihydrofuro[2,3-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With (4S,7R,8S)-4-((R)-1-((tert-butyldiphenylsilyl)oxy)ethyl)-1-(3,5-dimethoxyphenyl)-8,11,11-trimethyl-6-oxo-7-(perfluorobenzamido)-2,2,10,10-tetraphenyl-9-oxa-5-aza-2-phospha-10-siladodecan-2-ium bromide; sodium hydrogencarbonate In hexane at 20℃; for 48h; stereoselective reaction;
  • 92
  • [ 33094-66-5 ]
  • (E)-1-phenyl-4-(p-tolyl)but-3-en-1-one [ No CAS ]
  • (3aS,8aR)-3-((E)-4-methylstyryl)-2-phenyl-3a,8a-dihydrofuro[2,3-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With (4S,7R,8S)-4-((R)-1-((tert-butyldiphenylsilyl)oxy)ethyl)-1-(3,5-dimethoxyphenyl)-8,11,11-trimethyl-6-oxo-7-(perfluorobenzamido)-2,2,10,10-tetraphenyl-9-oxa-5-aza-2-phospha-10-siladodecan-2-ium bromide; sodium hydrogencarbonate In hexane at 20℃; for 48h; stereoselective reaction;
  • 93
  • [ 33094-66-5 ]
  • C16H13BrO [ No CAS ]
  • (3aS,8aR)-3-((E)-4-bromostyryl)-2-phenyl-3a,8a-dihydrofuro[2,3-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With (4S,7R,8S)-4-((R)-1-((tert-butyldiphenylsilyl)oxy)ethyl)-1-(3,5-dimethoxyphenyl)-8,11,11-trimethyl-6-oxo-7-(perfluorobenzamido)-2,2,10,10-tetraphenyl-9-oxa-5-aza-2-phospha-10-siladodecan-2-ium bromide; sodium hydrogencarbonate In hexane at 20℃; for 48h; stereoselective reaction;
  • 94
  • [ 33094-66-5 ]
  • (E)-4-(3-fluorophenyl)-1-phenylbut-3-en-1-one [ No CAS ]
  • (3aS,8aR)-3-((E)-3-fluorostyryl)-2-phenyl-3a,8a-dihydrofuro[2,3-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With (4S,7R,8S)-4-((R)-1-((tert-butyldiphenylsilyl)oxy)ethyl)-1-(3,5-dimethoxyphenyl)-8,11,11-trimethyl-6-oxo-7-(perfluorobenzamido)-2,2,10,10-tetraphenyl-9-oxa-5-aza-2-phospha-10-siladodecan-2-ium bromide; sodium hydrogencarbonate In hexane at 20℃; for 48h; stereoselective reaction;
  • 95
  • [ 33094-66-5 ]
  • (E)-4-(3-chlorophenyl)-1-phenylbut-3-en-1-one [ No CAS ]
  • (3aS,8aR)-3-((E)-3-chlorostyryl)-2-phenyl-3a,8a-dihydrofuro[2,3-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With (4S,7R,8S)-4-((R)-1-((tert-butyldiphenylsilyl)oxy)ethyl)-1-(3,5-dimethoxyphenyl)-8,11,11-trimethyl-6-oxo-7-(perfluorobenzamido)-2,2,10,10-tetraphenyl-9-oxa-5-aza-2-phospha-10-siladodecan-2-ium bromide; sodium hydrogencarbonate In hexane at 20℃; for 48h; stereoselective reaction;
  • 96
  • [ 33094-66-5 ]
  • (3E)-1,4-diphenylbut-3-en-1-one [ No CAS ]
  • 2-phenyl-3-((E)-styryl)-3a,8a-dihydrofuro[2,3-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate tribasic trihydrate; (4S,7R,8S)-4-((R)-1-((tert-butyldiphenylsilyl)oxy)ethyl)-1-(3,5-dimethoxyphenyl)-8,11,11-trimethyl-6-oxo-7-(perfluorobenzamido)-2,2,10,10-tetraphenyl-9-oxa-5-aza-2-phospha-10-siladodecan-2-ium bromide In methanol at 20℃; for 4h; stereoselective reaction;
  • 97
  • [ 33094-66-5 ]
  • C18H18O [ No CAS ]
  • (3aS,8aR)-2-(4-ethylphenyl)-3-((E)-styryl)-3a,8a-dihydrofuro[2,3-b]benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With (4S,7R,8S)-4-((R)-1-((tert-butyldiphenylsilyl)oxy)ethyl)-1-(3,5-dimethoxyphenyl)-8,11,11-trimethyl-6-oxo-7-(perfluorobenzamido)-2,2,10,10-tetraphenyl-9-oxa-5-aza-2-phospha-10-siladodecan-2-ium bromide; sodium hydrogencarbonate In hexane at 20℃; for 48h; stereoselective reaction;
  • 98
  • [ 33094-66-5 ]
  • [ 4636-43-5 ]
  • C18H14N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With C28H36F6N4O3 In dichloromethane at 20℃; for 24h; Inert atmosphere; Molecular sieve; 1 Synthesis of compound I-aa Add 0.2mmol of 2-nitrobenzofuran na, 0.26mmol of H-thiazolone m-a, 100mg of 5A molecular sieve and chiral catalyst A/B/C/D to a dry reaction test tube, and then add 2.0mL The solvent is reacted at room temperature under argon protection. After the reaction is complete, the crude product is separated and purified by column chromatography to obtain compound I-aa. The different reaction conditions are shown in Table 2. The specific reaction process is as follows:
  • 99
  • [ 33094-66-5 ]
  • C10H8FNOS [ No CAS ]
  • C18H13FN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With C28H36F6N4O3 In dichloromethane at 20℃; Inert atmosphere; Molecular sieve; 14 Synthesis of compound I-ac In a dry reaction tube, add 0.2mmol of 2-nitrobenzofuran II-a, 0.26mmol of 5H-thiazolone III-c, 100mg of 5A molecular sieve and chiral catalyst D 0.02mmol, and then add 2.0mL of dichloromethane was reacted at room temperature under argon protection; after the reaction was completed, the crude product was separated and purified by column chromatography to obtain compound I-ac.
  • 100
  • [ 33094-66-5 ]
  • C10H8ClNOS [ No CAS ]
  • C18H13ClN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With C28H36F6N4O3 In dichloromethane at 20℃; Inert atmosphere; Molecular sieve; 15 Synthesis of compound I-ad In a dry reaction tube, add 0.2mmol of 2-nitrobenzofuran II-a, 0.26mmol of 5H-thiazolone Ill-d, 100mg of 5A molecular sieve and chiral catalyst D 0.02mmol, and then add 2.0mL of dichloromethane was reacted at room temperature under argon protection; after the reaction was completed, the crude product was separated and purified by column chromatography to obtain compound I-ad.
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