(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl but-2-enedioate

• ChemBase ID: 156772
• Molecular Formular: C24H40O4
• Molecular Mass: 392.572
• Monoisotopic Mass: 392.29265976
• SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)/C=C/C(=O)O[C@H]1C[C@H](CC[C@@H]1C(C)C)C)C(C)C
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)/C=C/C(=O)O[C@H]1C[C@@H](C)CC[C@@H]1C(C)C)C(C)C
• InChI: InChI=1S/C24H40O4/c1-15(2)19-9-7-17(5)13-21(19)27-23(25)11-12-24(26)28-22-14-18(6)8-10-20(22)16(3)4/h11-12,15-22H,7-10,13-14H2,1-6H3/t17-,18+,19+,20-,21-,22+
• InChIKey: HTJZKHLYRXPLLS-RXGLGVBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl but-2-enedioate
• IUPAC Traditional name: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl but-2-enedioate
• Synonyms: (-)-Di[(1R)-menthyl] fumarate; (-)-二[(1R)-薄荷基]富马酸酯

Database IDs

• CAS Number: 34675-24-6
• MDL Number: MFCD00075423
• Beilstein Number: 2568525
• PubChem SID: 162250909; 24871637
• PubChem CID: 13294230

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 7.083241
• LogD (pH = 7.4): 7.083241
• Log P: 7.083241
• Molar Refractivity: 112.5132 cm^3
• Polarizability: 44.76109 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 62-64 °C
• Optical Rotation: [α]20/D -102±2°, c = 1% in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥94% (sum of enantiomers, HPLC)
• Grade: technical
• Empirical Formula (Hill Notation): C24H40O4

DETAILS

Sigma Aldrich - 47965

Other Notes
Chiral dienophile for asymmetric DA cycloadditions1,2,3,4; Synthesis of menthyl glyoxylate by ox. cleavage5