CAS 6674-22-2|1,8-Diazabicyclo[5.4.0]undec-7-ene|1,8-diazabicycloundec-7-ene|2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine|2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine|1,8-Diazabicycloundec-7-...

General Information

Structure

Molecular Formula

C₉H₁₆N₂

Molecular Mass

152.23674

Exact Mass

152.13134852

Charge

InChI

InChI=1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2

InChIKey

GQHTUMJGOHRCHB-UHFFFAOYSA-N

Canonic Smiles

C1CCN2C(=NCCC2)CC1

Isomeric Smiles

N12CCCCCC1=NCCC2

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-1.607904

LogD (pH = 7.4)

-1.5941415

Log P

0.80737644

Molar Refractivity

46.6048

Polarizability

17.711895

Polar Surface Area

15.6

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

1,8-Diazabicyclo[5.4.0]undec-7-ene2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepineDBU,Diazabicycloundecene1,8-Diazabicycloundec-7-eneDBU2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine1,8-Diazabicyclo-[5,4,0]undec-7-eneDBU solution2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine1,8-Diazabicyclo[5.4.0]undec-7-ene solution1,8-二氮杂双环[5.4.0]十一碳-7-烯溶液1,8-Diazabicyclo[5.4.0]undec-7-eneDBU 溶液2,3,4,6,7,8,9,10-八氢嘧啶并[1,2-a]氮杂卓1,8-二氮杂双环[5.4.0]十一碳-7-烯DBU1,8-二氮双环[5.4.0]十一-7-烯

IUPAC Traditional name

1,8-diazabicycloundec-7-ene

IUPAC name

2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine

Names and Identifiers

Registration numbers

CAS Number

6674-22-2

MDL Number

MFCD00006930

Wikipedia Title

1,8-Diazabicycloundec-7-ene

PubChem SID

248602582484837316203323124860259

Chemspider ID

Beilstein Number

EC Number

PubChem CID

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

1,8-Diazabicycloundec-7-ene

Sigma Aldrich

714852

Packaging
100 mL in Sure/Seal™

714860

Packaging
100 mL in Sure/Seal™

139009

Application
Halogenated Diels-Alder adducts were dehydrohalogenated with this base, and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3).2
Used in a new synthesis of the ABCD ring system of Camptothecin.
Features and Benefits
Strong hindered amine base.
Packaging
25, 100, 500 g in glass bottle
Citation
An application review.1

33482

Other Notes
Amidine base used for dehydrohalogenation reactions to olefins1; Further important applications are e.g.: esterification of carboxylic acids with alkyl halides2,3; Alkylation and acylation of active methylene compounds4

Molecule Details

References

PubChem Literature

From Data Sources

• Widely used as a base in elimination reactions, cf 1,5-Diazabicyclo[4.3.0]non-5-ene, A13437. For use in dehydrohalogenation, see, e.g. Org. Synth. Coll., 9, 247, 663 (1998).

• For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).

• For use in the enantioselective conversion of benzylic alcohols to azides, see Diphenylphosphonic azide, A12124.

• In combination with NBS in MeOH, promotes the Hofmann rearrangement of amides to give methyl carbamates under mild conditions: J. Org. Chem., 62, 7495 (1997).

• DBU forms hydrogen-bonded complexes with carboxylic acids, which can be alkylated in good yield by alkyl bromides or iodides, in a simple esterification procedure: Bull. Chem. Soc. Jpn., 51, 2401 (1978).

• Promotes the epoxidation of ɑ?-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995).

• Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).

• Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

1,8-diazabicycloundec-7-ene

IUPAC name

2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine

Registration numbers

CAS Number

6674-22-2

MDL Number

MFCD00006930

Wikipedia Title

1,8-Diazabicycloundec-7-ene

PubChem SID

248602582484837316203323124860259

Chemspider ID

Beilstein Number

EC Number

PubChem CID

Molecule Details

1,8-Diazabicycloundec-7-ene

Sigma Aldrich

714852

Packaging
100 mL in Sure/Seal™

714860

Packaging
100 mL in Sure/Seal™

139009

33482

References

PubChem Literature

From Data Sources

• Widely used as a base in elimination reactions, cf 1,5-Diazabicyclo[4.3.0]non-5-ene, A13437. For use in dehydrohalogenation, see, e.g. Org. Synth. Coll., 9, 247, 663 (1998).

• For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).

• For use in the enantioselective conversion of benzylic alcohols to azides, see Diphenylphosphonic azide, A12124.

• In combination with NBS in MeOH, promotes the Hofmann rearrangement of amides to give methyl carbamates under mild conditions: J. Org. Chem., 62, 7495 (1997).

• Promotes the epoxidation of ɑ?-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995).

• Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).

• Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966).

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:67496