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18422-53-2 molecular structure
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(3aR,6S,7aR)-2,2,5',5'-tetramethyl-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one

ChemBase ID: 146837
Molecular Formular: C12H18O6
Molecular Mass: 258.26772
Monoisotopic Mass: 258.1103383
SMILES and InChIs

SMILES:
CC1(OC[C@]2(O1)C(=O)[C@H]1[C@@H](CO2)OC(O1)(C)C)C
Canonical SMILES:
O=C1[C@@H]2OC(O[C@@H]2CO[C@@]21COC(O2)(C)C)(C)C
InChI:
InChI=1S/C12H18O6/c1-10(2)15-6-12(18-10)9(13)8-7(5-14-12)16-11(3,4)17-8/h7-8H,5-6H2,1-4H3/t7-,8-,12+/m1/s1
InChIKey:
IVWWFWFVSWOTLP-RWYTXXIDSA-N

Cite this record

CBID:146837 http://www.chembase.cn/molecule-146837.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3aR,6S,7aR)-2,2,5',5'-tetramethyl-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one
IUPAC Traditional name
(3aR,6S,7aR)-2,2,5',5'-tetramethyl-dihydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one
Synonyms
Shi’s epoxidation catalyst
1,2:4,5-Di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose
Shi Epoxidation Diketal Catalyst
1,2:4,5-Di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose
D-Epoxone
1,2:4,5-二-O-异亚丙基-β-D-赤式-2,3-二酮-2,6-吡喃糖
D-1,2:4,5-二邻异丙二烯-B-D-红-2,-己基
D-1,2:4,5-二邻异丙二烯-B-D-红-2,3-己基
CAS Number
18422-53-2
EC Number
000-000-0
MDL Number
MFCD00063383
MFCD11865369
Beilstein Number
1319073
PubChem SID
24874093
162241029
PubChem CID
7275400

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 7275400 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 15.104746  H Acceptors
H Donor LogD (pH = 5.5) 1.4142153 
LogD (pH = 7.4) 1.4142153  Log P 1.4142153 
Molar Refractivity 60.0832 cm3 Polarizability 24.3432 Å3
Polar Surface Area 63.22 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
101-103°C expand Show data source
102-104 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -120.9°, c = 1 in chloroform expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
98% expand Show data source
Empirical Formula (Hill Notation)
C12H18O6 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 520160 external link
Application
This organocatalyst is able to epoxidize trans alkenes and certain cis alkenes with good to excellent yields and selectivities.1,2,3,4,5
Packaging
5 g in glass bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Developed by Shi's group for the enantioselective epoxidation of alkenes. Used in substoichiometric amounts in the presence of OxoneTM or hydrogen peroxide, a chiral dioxirane is formed which converts trans-disubstituted and trisubstituted alkenes to epoxides with high ee: J. Am. Chem. Soc., 119, 11224 (1997); Tetrahedron Lett., 40, 8721 (1999). Selective monoepoxidation of dienes: J. Org. Chem., 63, 2948 (1998), or enynes: Tetrahedron Lett., 39, 4425 (1998), can be achieved. Has also been applied to the kinetic resolution of racemic cyclic olefins: J. Am. Chem. Soc., 121, 7718 (1999).
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PATENTS

PATENTS

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INTERNET

INTERNET

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