797-98-8

Basic information

• Product Name: 6H-Indeno[1,2-b]oxiren-6-one, 1a,6a-dihydro-1a,6a-diphenyl-
• Synonyms: 2,3-Epoxy-2,3-diphenyl-indan-1-on;2,3-diphenylindenone oxide;2,3-diphenylindenone 2,3-epoxide;2,3-Epoxy-2,3-diphenylindanone;2,3-epoxy-2,3-diphenyl-indan-1-one;2,3-diphenyl-2,3-epoxy-1-indanone
• CAS NO: 797-98-8
• Molecular Formula: C21H14O2
• Molecular Weight: 298.341
• Mol File: 797-98-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 6H-Indeno[1,2-b]oxiren-6-one, 1a,6a-dihydro-1a,6a-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-Indeno[1,2-b]oxiren-6-one, 1a,6a-dihydro-1a,6a-diphenyl-(797-98-8)
• EPA Substance Registry System: 6H-Indeno[1,2-b]oxiren-6-one, 1a,6a-dihydro-1a,6a-diphenyl-(797-98-8)

Safety Data

• Hazardous Substances Data: 797-98-8(Hazardous Substances Data)

Usage

General Description

6H-Indeno[1,2-b]oxiren-6-one, 1a,6a-dihydro-1a,6a-diphenyl- is a chemical compound that belongs to the oxirene family. It is a dihydro derivative with a 1a,6a-diphenyl substitution pattern. 6H-Indeno[1,2-b]oxiren-6-one, 1a,6a-dihydro-1a,6a-diphenyl- is a potential intermediate in organic synthesis and has applications in pharmaceutical and material science research. It is a cyclic ketone with a six-membered ring containing an oxirene moiety, and the diphenyl substitution adds to its potential reactivity and versatility in chemical reactions. As a dihydro compound, it may have unique physical and chemical properties that make it of interest to researchers in the field of organic chemistry.

Synthetic route

diazoacetic acid ethyl ester (623-73-4) + 10-tert-butyl-1,9-diphenyl-12-oxa-11-phosphatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraen-8-one → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + ethyl 5-tert-butyl-[1,2,4]-diazaphosphole-3-carboxylate

Conditions	Yield
In dichloromethane at 0 - 20℃; for 24h; addition; decomposition;	A n/a B 45%

2,3-diphenyl-1H-indene (5324-00-5) → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8)

Conditions	Yield
With potassium permanganate; acetic acid; acetone

2,3-diphenyl-1H-inden-1-one (1801-42-9) → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8)

Conditions	Yield
With sodium hydroxide; ethanol; dihydrogen peroxide

2,3-diphenyl-indan-1-one (7474-64-8) → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8)

Conditions	Yield
With pyridine; 9-benzyl-fluoren-9-yl hydroperoxide; N-benzyl-trimethylammonium hydroxide

1,3-Diphenyl-2-benzopyrylia-4-oxide (2669-83-2) → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8)

Conditions	Yield
In solid at 24.9 - 64.9℃; Rate constant; Kinetics; in dark;

(+-)-1,2-diphenyl-indene → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8)

Conditions	Yield
With potassium permanganate; acetic acid; acetone

Dichlorodiphenylmethane (2051-90-3) → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + glacial acetic acid-sulfuric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 230 °C / Behandlung des erhaltenen Gemischs mit konz. Schwefelsaeure 2: NaOH-solution; alcohol; hydrogen peroxide View Scheme

2,3,3-triphenylacrylic acid (4452-05-5) → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + glacial acetic acid-sulfuric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid; sulfuric acid 2: NaOH-solution; alcohol; hydrogen peroxide View Scheme

methyl 2,3,3-triphenylacrylate (181224-77-1) → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + glacial acetic acid-sulfuric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: NaOH-solution; alcohol; hydrogen peroxide View Scheme

benzeneacetic acid methyl ester (101-41-7) → 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + glacial acetic acid-sulfuric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 230 °C / Behandlung des erhaltenen Gemischs mit konz. Schwefelsaeure 2: NaOH-solution; alcohol; hydrogen peroxide View Scheme

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + 1,4-diphenyl-but-2-yne-1,4-dione (1087-09-8) → 10,11-Dibenzoyl-1,9-diphenyl-12-oxa-tricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraen-8-one (106976-64-1)

Conditions	Yield
In various solvent(s) for 0.5h; Heating;	92%

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + phenylpropynoic acid methyl ester (4891-38-7) → 8-Oxo-1,9,10-triphenyl-12-oxa-tricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraene-11-carboxylic acid methyl ester (106976-70-9)

Conditions	Yield
In various solvent(s) for 0.5h; Heating;	86%

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + ethenetetracarbonitrile (670-54-2) → 4,7-Epoxy-5,5,6,6-tetracyano-4,7-diphenyl-3-benzo<1,2>cycloheptenone (90448-17-2)

Conditions	Yield
In benzene at 20℃; Irradiation;	85%

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + phenylacetylene (536-74-3) → 1,9,10-Triphenyl-12-oxa-tricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraen-8-one (106976-72-1)

Conditions	Yield
In various solvent(s) for 0.5h; Heating;	82%

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + 2,2-dimethylpropylidynephosphine (78129-68-7) → 10-tert-butyl-1,9-diphenyl-12-oxa-11-phosphatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraen-8-one

Conditions	Yield
In dichloromethane at 150℃; under 3750.3 Torr; for 18h; Cycloaddition;	75%
In dichloromethane at 150℃; under 3750.38 Torr; for 18h; Cycloaddition;	75%

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + tert-pentylphosphaacetylene (117972-60-8) → 10-(1,1-dimethylpropyl)-1,9-diphenyl-12-oxa-11-phosphatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraen-8-one

Conditions	Yield
In dichloromethane at 150℃; under 3750.3 Torr; for 18h; Cycloaddition;	70%

1,2-dicarbomethoxycyclobutene (1128-10-5) + 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) → C29H24O6

Conditions	Yield
In toluene for 72h; Heating;	60%

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + 1-adamantylphosphaacetylene (101055-70-3) → 10-(adamantan-1-yl)-1,9-diphenyl-12-oxa-11-phosphatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraen-8-one

Conditions	Yield
In dichloromethane at 150℃; under 3750.3 Torr; for 18h; Cycloaddition;	52%

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + (1-Methylcyclohexyl)methylidynephosphane (101055-71-4) → 10-(1-methylcyclohexyl)-1,9-diphenyl-12-oxa-11-phosphatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraen-8-one

Conditions	Yield
In dichloromethane at 150℃; under 3750.3 Torr; for 18h; Cycloaddition;	28%

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) → 3-chloro-2-hydroxy-2,3-diphenyl-indan-1-one

Conditions	Yield
With hydrogenchloride; acetic acid

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + benzonitrile (100-47-0) → 1,3,4-triphenyl-1,4-dihydro-1,4-epioxido-benzo[c]azepin-5-one (103799-06-0)

Conditions	Yield
at 145 - 150℃;

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) → 1,3-Diphenyl-2-benzopyrylia-4-oxide (2669-83-2)

Conditions	Yield
In benzene at 20℃; Quantum yield; Irradiation; photoisomerization;
In solid Thermodynamic data; Rate constant; Ambient temperature; Irradiation; Ea(excit.); also 4,7-dimethyl substituted compound;
Irradiation;

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + ethanolic KOH-solution → 1,3-diphenylisobenzofuran (5471-63-6)

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + hydrogen chloride-glacial acetic acid → 2.3-dioxy-2.3-diphenyl-hydrindone-(1)

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + glacial acetic acid-sulfuric acid → 3,4-diphenyl-isochromen-1-one (1684-07-7)

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + acetic acid (64-19-7) → 3,4-diphenyl-isochromen-1-one (1684-07-7) + 2.3-dioxy-2.3-diphenyl-hydrindone-(1)

2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + hydrogen bromide-glacial acetic acid → 3,4-diphenyl-isochromen-1-one (1684-07-7) + 2.3-dioxy-2.3-diphenyl-hydrindone-(1)

hydrogenchloride (7647-01-0) + 2,3-diphenyl-2,3-epoxy-1-indanone (797-98-8) + acetic acid (64-19-7) → 3-chloro-2-hydroxy-2,3-diphenyl-indan-1-one

Upstream product

• 1801-42-9 2,3-diphenyl-1H-inden-1-one 
• 101-41-7 benzeneacetic acid methyl ester 
• 181224-77-1 methyl 2,3,3-triphenylacrylate 
• 4452-05-5 2,3,3-triphenylacrylic acid 
• 2051-90-3 Dichlorodiphenylmethane 
• 623-73-4 diazoacetic acid ethyl ester 
• 2669-83-2 1,3-Diphenyl-2-benzopyrylia-4-oxide 
• 7474-64-8 2,3-diphenyl-indan-1-one 
• 5324-00-5 2,3-diphenyl-1H-indene 

Downstream Products

• 5471-63-6 1,3-diphenylisobenzofuran 
• 36213-48-6 2,4,10-triphenyl-(3ac,10ac)-3a,4,10,10a-tetrahydro-4r,10c-epioxido-benzo[4,5]cyclohepta[1,2-c]pyrrole-1,3,9-trione 
• 36547-65-6 4,10-diphenyl-(3ac,10ac)-3a,4,10,10a-tetrahydro-4r,10c-epioxido-benzo[4,5]cyclohepta[1,2-c]pyrrole-1,3,9-trione 
• 1684-07-7 3,4-diphenyl-isochromen-1-one 
• 2669-83-2 1,3-Diphenyl-2-benzopyrylia-4-oxide 
• 106976-64-1 10,11-Dibenzoyl-1,9-diphenyl-12-oxa-tricyclo[7.2.1.0^2,7]dodeca-2,4,6,10-tetraen-8-one 
• 106976-72-1 1,9,10-Triphenyl-12-oxa-tricyclo[7.2.1.0^2,7]dodeca-2,4,6,10-tetraen-8-one 
• 106976-70-9 8-Oxo-1,9,10-triphenyl-12-oxa-tricyclo[7.2.1.0^2,7]dodeca-2,4,6,10-tetraene-11-carboxylic acid methyl ester 
• 90448-17-2 4,7-Epoxy-5,5,6,6-tetracyano-4,7-diphenyl-3-benzo<1,2>cycloheptenone 
• 103799-06-0 1,3,4-triphenyl-1,4-dihydro-1,4-epioxido-benzo[c]azepin-5-one 

Relevant articles and documents

Organophosphorus compounds, 145 - Synthesis and reactivity of a polycyclic, oxa-bridged phosphaalkene

Thermolysis of 2,3-diphenylindenone 2,3-epoxide (1) in the presence of tert-butylphosphaalkyne (3) proceeds through a regiospecific 1,3-dipolar cycloaddition of the phosphaalkyne to the carbonyl ylide intermediate to furnish the polycyclic phosphaalkene derivative 4. Compound 4 exhibits a remarkable - and for phosphaalkenes unusual - stability: thus, it can be stored for several days and no decomposition can be observed even in the absence of inert gas protection. The phosphaalkene 4 reacts with 1,3-dipoles such as ethyl diazoacetate (8) by formal transfer of its phosphaalkene unit to afford the 1,2,4-diazaphosphole 10. Addition of lithium alkoxides to the phosphaalkene unit of the polycyclic compound 4 occurs diastereoselectively to give the novel phosphinites 13 and 14. In this context it should be mentioned that the choice of the lithium alkoxide has a decisive influence on the preferred formation of one diastereomer of the phosphinite.