(2'S,3S,5'S,6'R,8'R,11'S)-4'-Methyl-2'-vinylspiro[indole-3,7'-[9]oxa[4]azatetracyclo[6.3.1.0~2,6~.0~5,11~]dodecan]-2(1H)-one

Basic Information

View in Editor

CAS Number

509-15-9

Molecular Formula

C20H22N2O2

Molecular Weight

322.41 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

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

Basic Physical Properties

Physical State

Powder

Melting Point

181-183°C

Boiling Point

493.4°C at 760 mmHg

Solubility

SLIGHTLY SOL IN WATER; SOL IN ALCOHOL, BENZENE, CHLOROFORM, ETHER, ACETONE, DILUTE ACIDS

Refractive Index

1.5700 (estimate)

Specific Rotation

D20 +13° (c = 1.2 in chloroform)

SMILES

View in Editor

CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6NC5=O)C=C

InChI

InChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11-,13?,15?,16+,17-,19-,20-/m0/s1

InChIKey

NFYYATWFXNPTRM-XXVYUQGQSA-N

LogP

2.0275999999999996

pKa

7.75 in 80% methylcellosolve

Topological Polar Surface Area

41.57 Å²

Hydrogen Bond Donor/Acceptor

1 / 4

Complexity

635

Safety Information

View Safety Information

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Hazard Class

Class 6.1(a) Class 6.1(a)

Storage Conditions

2-8℃

Synonyms & References

English

GELSEMINE
(+)-Gelsemine
GELSEMINE, (+)-
Gelsemin
AC-34231
509-15-9
s9294
4-27-00-07526 (Beilstein Handbook Reference)
MFCD00082347
GELSEMINE [MI]
GELSEMINE [WHO-DD]
GELSEMIN [HSDB]
Spiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, (3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-
(3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methylspiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1',H)-one
EINECS 208-095-2
(3S,3aS,3'S,5R,8aS,9R)-1-Methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-(epiethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indolin]-2'-one
BRN 5406576
5Y13A78Z72
UNII-5Y13A78Z72
NSC-21729
1ST40269
SPIRO(3,5,8-ETHANYLYLIDENE-1H-PYRANO(3,4-C)PYRIDINE-10,3'-(3H)INDOL)-2'(1'H)-ONE, 5-ETHENYL-3,4,4A,5,6,7,8,8A-OCTAHYDRO-7-METHYL-, (3R-(3.ALPHA.,4A.BETA.,5.ALPHA.,8.ALPHA.,8.ABETA.,9S*,10S*))-
Spiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, (3R,3'S,4aR,5S,8S,8aS,9S)-
CHEMBL521561
gelsemine free base
(3R-(3.ALPHA.,4A.BETA.,5.ALPHA.,8.ALPHA.,8A.BETA.,9S*,10S*))-5-ETHENYL-3,4,4A,5,6,7,8,8A-OCTAHYDRO-7-METHYLSPIRO(3,5,8-ETHANYLYLIDENE-1H-PYRANO(3,4-C)PYRIDINE-10,3'-(3H)INDOL)-2'(1'H)-ONE
BDBM50459893
HSDB 3488
CCG-267730
NSC 21729
Gelsemine

MDL Number

MFCD00082347

FAQ

What is (2'S,3S,5'S,6'R,8'R,11'S)-4'-Methyl-2'-vinylspiro[indole-3,7'-[9]oxa[4]azatetracyclo[6.3.1.0~2,6~.0~5,11~]dodecan]-2(1H)-one (CAS: 509-15-9)?

This is a complex organic compound with the CAS number 509-15-9. It features a spiro system connecting an indole ring to a tetrahydrofuran ring, along with multiple stereocenters and a methyl group. The compound is known for its potential biological activity and is often studied in the context of pharmaceutical research due to its structural complexity and functional groups.

What are the main uses of (2'S,3S,5'S,6'R,8'R,11'S)-4'-Methyl-2'-vinylspiro[indole-3,7'-[9]oxa[4]azatetracyclo[6.3.1.0~2,6~.0~5,11~]dodecan]-2(1H)-one (CAS: 509-15-9)?

This compound is primarily used in pharmaceutical research for its potential therapeutic applications. It may serve as a lead molecule in drug development due to its unique structure and reactivity. Additionally, it is studied in organic chemistry for structural analysis and synthetic pathways, contributing to the understanding of complex ring systems and stereochemistry.

Is (2'S,3S,5'S,6'R,8'R,11'S)-4'-Methyl-2'-vinylspiro[indole-3,7'-[9]oxa[4]azatetracyclo[6.3.1.0~2,6~.0~5,11~]dodecan]-2(1H)-one (CAS: 509-15-9) safe?

Safety data for this compound is limited, but as with many complex organic molecules, it should be handled with care. Precautions include using appropriate personal protective equipment (PPE) and working in a well-ventilated area. It is recommended to follow standard chemical safety protocols to minimize exposure risks and ensure safe handling during experimentation.

How should (2'S,3S,5'S,6'R,8'R,11'S)-4'-Methyl-2'-vinylspiro[indole-3,7'-[9]oxa[4]azatetracyclo[6.3.1.0~2,6~.0~5,11~]dodecan]-2(1H)-one (CAS: 509-15-9) be stored?

This compound should be stored in a cool, dry, and dark place to maintain stability. It is best kept in a sealed container away from air and moisture. For long-term storage, a temperature range of 2-8°C is recommended, and exposure to light should be minimized to prevent degradation.