2,5-dioxopyrrolidin-1-yl (1r,4r)-4-(propan-2-yl)cyclohexane-1-carboxylate

• ChemBase ID: 171321
• Molecular Formular: C14H21NO4
• Molecular Mass: 267.32084
• Monoisotopic Mass: 267.14705816
• SMILES: C1[C@H](CC[C@@H](C1)C(=O)ON1C(=O)CCC1=O)C(C)C
• Canonical SMILES: CC([C@@H]1CC[C@H](CC1)C(=O)ON1C(=O)CCC1=O)C
• InChI: InChI=1S/C14H21NO4/c1-9(2)10-3-5-11(6-4-10)14(18)19-15-12(16)7-8-13(15)17/h9-11H,3-8H2,1-2H3/t10-,11-
• InChIKey: UXLRCUGBVTVSEE-XYPYZODXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl (1r,4r)-4-(propan-2-yl)cyclohexane-1-carboxylate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl (1r,4r)-4-isopropylcyclohexane-1-carboxylate
• Synonyms: trans-4-(1-Methylethyl)cyclohexanecarboxylic Acid 2,5-Dioxo-1-pyrrolidinyl Ester; 4-trans-Isopropylcyclohexanecarboxylic Acid, N-Succunimidyl Ester; N-Hydroxysuccinimidyl trans-4-Isopropylcyclohexanecarboxylate

Database IDs

• CAS Number: 183997-00-4
• PubChem SID: 164227231
• PubChem CID: 12132275

CALCULATED PROPERTIES

• Acid pKa: 17.70829
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.2783487
• LogD (pH = 7.4): 2.2783487
• Log P: 2.2783487
• Molar Refractivity: 68.0979 cm^3
• Polarizability: 27.161469 Å^3
• Polar Surface Area: 63.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; THF
• Apperance: White Cyrstalline Solid
• Melting Point: 128-130°C

DETAILS

Toronto Research Chemicals - H953675

N-Hydroxysuccinimidyl trans-4-Isopropylcyclohexanecarboxylate is an intermediate used in the process for synthesizing highly enantiopure Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent

REFERENCES

• Takesada, H., et al.: Bioorg. Med. Chem., 5, 637 (1997)