(1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate

Basic Information

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CAS Number

51-34-3

Molecular Formula

C17H21NO4

Molecular Weight

303.36 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

Basic Physical Properties

Physical State

Oil

Melting Point

59oC

Boiling Point

460.3°C at 760 mmHg

Flash Point

232.2°C

Solubility

0.32 M

Refractive Index

1.5022 (estimate)

Vapor Pressure

7.18X10-9 mm Hg at 25 °C (est)

Specific Rotation

D20 -28° (c = 2.7)

SMILES

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CN1[C@H]2C[C@@H](C[C@@H]1[C@H]3O[C@H]32)OC(=O)[C@H](CO)c4ccccc4

InChI

InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1

InChIKey

STECJAGHUSJQJN-FWXGHANASA-N

LogP

0.9180999999999993

pKa

7.55-7.81(at 25℃)

Topological Polar Surface Area

62.3 Å²

Hydrogen Bond Donor/Acceptor

1 / 5

Complexity

418

Synonyms & References

English

Scopolamine
9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-alpha-(hydroxymethyl)benzeneacetate
Hyoscine
LCZ696
Scopine (-)-tropate
Scopine tropate
(-)-Hyoscine
Transderm-Scop
6,7-Epoxytropine tropate
(-)-Scopolamine
Isopto Hyoscine
Hyosol
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate
Atroquin
Atrochin
Oscine
Transderm scop
Epoxytropine tropate
alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester
Skopolamin
l-Scopolamine
DL48G20X8X
(1S,3S,5R,6R,7S)-6,7-epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoat
(1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (S)-3-hydroxy-2-phenylpropanoate

MDL Number

MFCD00865260

FAQ

What are the physical and chemical properties of (1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate (CAS: 51-34-3)?

This compound is a crystalline solid with a molecular weight of approximately 269.33 g/mol. It is slightly soluble in water and has good solubility in organic solvents. Chemically, it is highly reactive towards nucleophiles and can undergo various transformations like hydrolysis and esterification. It is also prone to ring-opening reactions under basic conditions.

How is (1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate (CAS: 51-34-3) typically synthesized?

This compound is typically synthesized via a multistep process involving the construction of the tricyclic backbone, followed by the introduction of the 9-amino group and the phenyl ester functionality. Common catalysts include Lewis acids like boron trifluoride, and the overall yield ranges from 60-80%. Selectivity towards the correct stereochemistry is achieved using chiral auxiliaries and enantioselective reagents.

What industries use (1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate (CAS: 51-34-3)?

This compound is primarily used in the pharmaceutical industry due to its structural complexity and potential as a drug lead. It may also find applications in polymer chemistry for developing functional materials, and in chemical sensors for detecting specific analytes. Its unique structure makes it particularly interesting for advanced material science research.

What precautions should be taken when handling (1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate (CAS: 51-34-3)?

When handling this compound, it is essential to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or fume hood to minimize inhalation risk. Spills should be immediately contained and handled according to the Material Safety Data Sheet (MSDS) guidelines. Ensure proper disposal and storage to prevent environmental contamination.