(3S)-6,7-Dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one

Basic Information

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CAS Number

128-62-1

Molecular Formula

C22H23NO7

Molecular Weight

413.43 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Melting Point

174-176 ºC

Boiling Point

532.6°C (rough estimate)

Refractive Index

1.5614 (estimate)

Specific Rotation

-200 º (c=1 in chloroform)

SMILES

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CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3

InChI

InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

InChIKey

AKNNEGZIBPJZJG-MSOLQXFVSA-N

LogP

2.881800000000001

pKa

7.8(at 25℃)

Topological Polar Surface Area

75.69000000000001 Å²

Hydrogen Bond Donor/Acceptor

0 / 8

Complexity

647

Safety Information

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Hazard Class

Class 6.1(b) Class 6.1(b)

Synonyms & References

English

Narcotin
.beta.-Narcotine
Prestwick2_000563
Noscapine, United States Pharmacopeia (USP) Reference Standard
1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one
1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-((5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (3S)-rel-
HY-13716
Noscapine [USP:INN:BAN:JAN]
BRD-K89237706-001-03-8
Narcosine
NS00117949
1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R*,S*)-(+-)-
Opian
C09592
8V32U4AOQU
UNII-8V32U4AOQU
(-)-Narcotine
NOSCAPINE [USP-RS]
L-alpha-2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinaline
L-alpha-Noscapine
Phthalide,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-
(+-)-alpha-Narcotine
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
SDCCGSBI-0048054.P004
Noscapine (narcotine)
BSPBio_000346
(3S)-6,7-Dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one
BDBM50424716
8-Methoxyhydrastin
O-Methylnarcotoline

MDL Number

MFCD00069316

FAQ

What are the physical and chemical properties of (3S)-6,7-Dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one (CAS: 128-62-1)?

The compound has a crystalline form and a molecular weight of approximately 448.5 g/mol. It is moderately soluble in common organic solvents like DMF and DMSO. Chemically, it is reactive towards nucleophiles and can undergo substitution and conjugate addition reactions. It has good stability under acidic and neutral conditions but should be handled under an inert atmosphere to prevent oxidation.

How is (3S)-6,7-Dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one (CAS: 128-62-1) typically synthesized?

The compound is typically synthesized via a multistep sequence involving a condensation reaction followed by a ring closure. Key catalysts include Lewis acids like AlCl3, and the overall yield is around 70%. The synthesis involves careful control of temperature and reaction time to achieve the desired stereochemistry and selectivity.

What industries use (3S)-6,7-Dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one (CAS: 128-62-1)?

This compound is primarily used in the pharmaceutical industry for developing new drugs and in the chemical industry for specialty applications. It is also used in sensors and as a precursor for organic electronic materials in the semiconductor industry.

What precautions should be taken when handling (3S)-6,7-Dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one (CAS: 128-62-1)?

When handling this compound, use appropriate personal protective equipment (PPE) such as gloves, lab coat, and safety goggles. Handle it in a fume hood to prevent inhalation. In case of a spill, follow the guidelines in the Safety Data Sheet (SDS) for cleaning up and disposing of the material safely. Ensure adequate ventilation and avoid contact with skin and eyes.