(2S)-2-[(1R,2R,6S,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]pyrrolidine hydrochloride

• ChemBase ID: 176738
• Molecular Formular: C14H25BClNO2
• Molecular Mass: 285.6178
• Monoisotopic Mass: 285.16668713
• SMILES: Cl.[C@H]12C([C@H]([C@@]3([C@H](C1)OB(O3)[C@H]1CCCN1)C)C2)(C)C
• Canonical SMILES: C[C@]12OB(O[C@H]1C[C@H]1C[C@@H]2C1(C)C)[C@H]1CCCN1.Cl
• InChI: InChI=1S/C14H24BNO2.ClH/c1-13(2)9-7-10(13)14(3)11(8-9)17-15(18-14)12-5-4-6-16-12;/h9-12,16H,4-8H2,1-3H3;1H/t9?,10?,11-,12+,14+;/m0./s1
• InChIKey: OVVMNBVQOPZMPY-VZCNYRSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(1R,2R,6S,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,^6]decan-4-yl]pyrrolidine hydrochloride
• IUPAC Traditional name: (2S)-2-[(1R,2R,6S,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,^6]decan-4-yl]pyrrolidine hydrochloride
• Synonyms: (2S)-2-[(3aR,4R,6R,7aS)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]pyrrolidine Hhydrochloride; [3aR-[2(S*),3aα,4β,6β,7aα]]-2-(Hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl)pyrrolidine Hydrochloride; (1R,2R,3S,5R)-Pinanediol Pyrrolidine-2S-boronate Hydrochloride

Database IDs

• CAS Number: 149716-73-4
• PubChem SID: 164232648
• PubChem CID: 49853524

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.12561804
• LogD (pH = 7.4): 0.56126344
• Log P: 3.4595
• Molar Refractivity: 65.2802 cm^3
• Polarizability: 28.495853 Å^3
• Polar Surface Area: 30.49 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P458605

Used in the preparation of prolineboronate esters.

REFERENCES

• Koehler, K.A., et al.: Biochemistry, 10, 2477 (1971)
• Kettner, C.A., et al.: J. Biol. Chem., 259, 15106 (1971)