(1S,2S,6R,8S)-4-(3-bromopropyl)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane

• ChemBase ID: 163038
• Molecular Formular: C13H22BBrO2
• Molecular Mass: 301.02758
• Monoisotopic Mass: 300.08962234
• SMILES: [C@H]12C([C@H]([C@]3([C@@H](C1)OB(O3)CCCBr)C)C2)(C)C
• Canonical SMILES: BrCCCB1O[C@H]2[C@](O1)(C)[C@@H]1C[C@H](C2)C1(C)C
• InChI: InChI=1S/C13H22BBrO2/c1-12(2)9-7-10(12)13(3)11(8-9)16-14(17-13)5-4-6-15/h9-11H,4-8H2,1-3H3/t9-,10-,11+,13-/m0/s1
• InChIKey: IFWLNKNUIWTYGB-KQXIARHKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6R,8S)-4-(3-bromopropyl)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,^6]decane
• IUPAC Traditional name: (1S,2S,6R,8S)-4-(3-bromopropyl)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,^6]decane
• Synonyms: (3aS,4S,6S,7aR)-2-(3-Bromopropyl)hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole; (+)-Pinanediol 3-Bromopropylboronate; [3aS-(3aα,4β,6β,7aα)]-2-(3-Bromopropyl)hexahydro-3a,5,5-trimethyl-4,6-Methano-1,3,2-benzodioxaborole; (+)-(3-Bromopropyl)boronic Acid Pinanediol Ester

Database IDs

• CAS Number: 90084-37-0
• PubChem SID: 162257173
• PubChem CID: 11012058

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.0498
• LogD (pH = 7.4): 4.0498
• Log P: 4.0498
• Molar Refractivity: 67.4316 cm^3
• Polarizability: 28.514297 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B686685

A pinanediol boronic ester derivative used in the preparation of thrombin inhibitors.

REFERENCES

• Kettner, C. et al.: J. Biol. Chem., 265, 18289 (1990)