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302911-95-1 molecular structure
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(3R,7aS)-7a-methyl-3-phenyl-2H,3H,5H,7aH-pyrrolo[2,1-b][1,3]oxazol-5-one

ChemBase ID: 137206
Molecular Formular: C13H13NO2
Molecular Mass: 215.24782
Monoisotopic Mass: 215.09462866
SMILES and InChIs

SMILES:
C[C@]12C=CC(=O)N1[C@@H](CO2)c1ccccc1
Canonical SMILES:
O=C1C=C[C@]2(N1[C@@H](CO2)c1ccccc1)C
InChI:
InChI=1S/C13H13NO2/c1-13-8-7-12(15)14(13)11(9-16-13)10-5-3-2-4-6-10/h2-8,11H,9H2,1H3/t11-,13-/m0/s1
InChIKey:
UFQSRYWJCHFOQX-AAEUAGOBSA-N

Cite this record

CBID:137206 http://www.chembase.cn/molecule-137206.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3R,7aS)-7a-methyl-3-phenyl-2H,3H,5H,7aH-pyrrolo[2,1-b][1,3]oxazol-5-one
IUPAC Traditional name
(3R,7aS)-7a-methyl-3-phenyl-2H,3H-pyrrolo[2,1-b][1,3]oxazol-5-one
Synonyms
(3R-cis)-(-)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one
(3R-顺)-(-)-2,3-二氢-7a-甲基-3-苯基吡咯并[2,1-b]噁唑-5(7aH)-酮
CAS Number
302911-95-1
MDL Number
MFCD00274330
PubChem SID
162231471
24869480
PubChem CID
2733461

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
458562 external link Add to cart Please log in.
Data Source Data ID
PubChem 2733461 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.9374771  LogD (pH = 7.4) 1.9374782 
Log P 1.9374783  Molar Refractivity 61.2106 cm3
Polarizability 23.415218 Å3 Polar Surface Area 29.54 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
90-92 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -124°, c = 1 in chloroform expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22 expand Show data source
Safety Statements
36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H332 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
98% expand Show data source
Optical Purity
ee: ≥99% (HPLC) expand Show data source
Empirical Formula (Hill Notation)
C13H13NO2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 458562 external link
Application
High levels of asymmetric induction1 have been obtained with this chiral bicyclic lactam in cycloadditions,2,3 alkylations,4,5,6 conjugate additions,7,8 annulations,9 and dihydroxylations.10

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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