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14805-29-9

Basic Information
CAS No.: 14805-29-9
Name: (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione
Article Data: 10
Cas Database
Molecular Structure:
Molecular Structure of 14805-29-9 ((3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione)
Formula: C9H11NO2
Molecular Weight: 165.192
Synonyms: 1H-4,7-Methanoisoindole-1,3(2H)-dione;NSC238001;AC1L8LM0;
EINECS: 689-268-3
Density: 1.55 g/cm3
Melting Point: 173-176℃
Boiling Point: 519.7 °C at 760 mmHg
Flash Point: 262.1 °C
Solubility: N/A
Appearance: white
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 46.17000
LogP: 0.63390
Synthetic route
6265-30-1

(1R,2S,6R,7S)-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol Autoclave; Industrial scale;91.4%
14166-28-0

exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran at 190℃; for 2h;80.5%
Multi-step reaction with 2 steps
1: triethylamine / toluene / Reflux
2: pyridine / 0 - 20 °C
View Scheme
Stage #1: exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride In tetrahydrofuran at 25 - 35℃; for 0.166667h;
Stage #2: With ammonia In tetrahydrofuran; water at 0 - 35℃;
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95.9 percent / H2 / 10percent Pd/C / H2O; tetrahydrofuran / 1.5 h / Ambient temperature
2: 80.5 percent / 7percent aq. NH3 / tetrahydrofuran / 2 h / 190 °C
View Scheme
Multi-step reaction with 2 steps
1: 95.9 percent / H2 / 10percent Pd-C/ 50percent H2O / tetrahydrofuran / 1.5 h / Ambient temperature
2: 80.5 percent / 7percent aq. NH3 / tetrahydrofuran / 2 h / 190 °C
View Scheme
Multi-step reaction with 2 steps
1.1: palladium on activated charcoal; hydrogen / 25 - 35 °C / 3750.38 Torr / Inert atmosphere; Autoclave
2.1: tetrahydrofuran / 0.17 h / 25 - 35 °C
2.2: 0 - 35 °C
View Scheme

(3aR,4S,7R,7aS)-2-(((1R,2R)-2-(hydroxymethyl)cyclohexyl)methy)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

124-63-0

methanesulfonyl chloride

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
Stage #1: (3aR,4S,7R,7aS)-2-(((1R,2R)-2-(hydroxymethyl)cyclohexyl)methy)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione; methanesulfonyl chloride With pyridine at 0 - 20℃;
Stage #2: With hydrogenchloride In water
542-92-7

cyclopenta-1,3-diene

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1 h / 200 °C
2.1: palladium on activated charcoal; hydrogen / 25 - 35 °C / 3750.38 Torr / Inert atmosphere; Autoclave
3.1: tetrahydrofuran / 0.17 h / 25 - 35 °C
3.2: 0 - 35 °C
View Scheme
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium acetate / 135 °C / Industrial scale
2: hydrogen; palladium 10% on activated carbon / methanol / Autoclave; Industrial scale
View Scheme
111-24-0

1,5-dibromo-pentane

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

138274-10-9

N-(4-Bromopentyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;100%
186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

((1R,2R)-2-(((3aR,4S,7R,7aS)-1,3-dioxohexahydro-1H-4,7-methanoisoindol-2(3H)-yl)methyl)cyclohexyl)methylmethanesulfonate

Conditions
ConditionsYield
With potassium carbonate In isopropyl alcohol for 4h;99%
186204-37-5

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

367514-88-3

(3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride

Conditions
ConditionsYield
Stage #1: (3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate; (3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione With potassium carbonate In toluene at 105℃; for 15h; Industrial scale;
Stage #2: With hydrogenchloride In isopropyl alcohol Industrial scale;
98.3%
Multi-step reaction with 2 steps
1.1: potassium carbonate; dibenzo-18-crown-6 / 5,5-dimethyl-1,3-cyclohexadiene / 3 h
2.1: methanol / 0.17 h / 60 - 65 °C
2.2: 1 h / 60 - 65 °C
View Scheme

C19H26N3S(1+)*CH3O3S(1-)

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

lurasidone

Conditions
ConditionsYield
With potassium carbonate In water for 10h; Reflux;95%
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87760-53-0
367514-88-3
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    Product name: (3aR,4S,7R,7aS)-4,7-Methano-1H-Isoindole-1,3(2H)-Dione CAS No.: 14805-29-9 Molecule Formula:C9H11NO2 Molecule Weight:165.19 Purity: 98.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Stand

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Specification

The (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione with CAS registry number of 14805-29-9 is also known as NSC238001. The systematic name is 1H-4,7-Methanoisoindole-1,3(2H)-dione. In addition, the formula is C9H11NO2 and the molecular weight is 159.14.

Physical properties about (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione are: (1)ACD/LogP: 0.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.29; (4)ACD/LogD (pH 7.4): 0.28; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.2; (8)ACD/KOC (pH 7.4): 33.81; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)Index of Refraction: 1.714; (12)Molar Refractivity: 40.28 cm3; (13)Molar Volume: 102.6 cm3; (14)Surface Tension: 62.4 dyne/cm; (15)Density: 1.55 g/cm3; (16)Flash Point: 262.1 °C; (17)Enthalpy of Vaporization: 79.25 kJ/mol; (18)Boiling Point: 519.7 °C at 760 mmHg; (19)Vapour Pressure: 6.67E-11 mmHg at 25 °C.

Preparation of (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione: it is prepared by reaction of norbornane-2exo,3exo-dicarboxylic acid-anhydride. The reaction needs reagent 7percent aq. NH3 and solvent tetrahydrofuran at the temperature of 190 °C for 2 hours. The yield is about 80.5%.

(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione is prepared by reaction of norbornane-2exo,3exo-dicarboxylic acid-anhydride.

Uses of (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione: it is used to produce N-(4-bromobutyl)bicyclo[2.2.1]heptane-2,3-di-exo-carboximide by reaction with 1,4-dibromo-butane. The reaction occurs with reagent K2CO3 and solvent acetone with other condition of heating for 7 hours. The yield is about 90.2%.

(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione is used to produce N-(4-bromobutyl)bicyclo[2.2.1]heptane-2,3-di-exo-carboximide by reaction with 1,4-dibromo-butane.

You can still convert the following datas into molecular structure:
1. SMILES: O=C2NC(=O)C=3\C\1=C\C=C(/C/1)\C2=3
2. InChI: InChI=1/C9H5NO2/c11-8-6-4-1-2-5(3-4)7(6)9(12)10-8/h1-2H,3H2,(H,10,11,12)
3. InChIKey: STMLHNAVHHLFKU-UHFFFAOYAK
4. Std. InChI: InChI=1S/C9H5NO2/c11-8-6-4-1-2-5(3-4)7(6)9(12)10-8/h1-2H,3H2,(H,10,11,12)
5. Std. InChIKey: STMLHNAVHHLFKU-UHFFFAOYSA-N