(1R,6S)-6-(methoxycarbonyl)cyclohex-3-ene-1-carboxylic acid

• ChemBase ID: 151421
• Molecular Formular: C9H12O4
• Molecular Mass: 184.18918
• Monoisotopic Mass: 184.07355886
• SMILES: COC(=O)[C@H]1CC=CC[C@H]1C(=O)O
• Canonical SMILES: COC(=O)[C@H]1CC=CC[C@H]1C(=O)O
• InChI: InChI=1S/C9H12O4/c1-13-9(12)7-5-3-2-4-6(7)8(10)11/h2-3,6-7H,4-5H2,1H3,(H,10,11)/t6-,7+/m1/s1
• InChIKey: MYYLMIDEMAPSGH-RQJHMYQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,6S)-6-(methoxycarbonyl)cyclohex-3-ene-1-carboxylic acid
• IUPAC Traditional name: (1R,6S)-6-(methoxycarbonyl)cyclohex-3-ene-1-carboxylic acid
• Synonyms: (1S,2R)-1-Methyl cis-4-cyclohexene-1,2-dicarboxylate; (1S,2R)-cis-4-Cyclohexene-1,2-dicarboxylic acid 1-monomethylester; (1S,2R)-1-Methyl cis-1,2,3,6-tetrahydrophthalate; (1S,2R)-1-Methyl cis-1,2,3,6-tetrahydrophthalate; (1S,2R)-cis-4-Cyclohexene-1,2-dicarboxylic acid 1-monomethyl ester; (1S,2R)-1-甲基 顺式-4-环己烯-1,2-二羧酸; (1S,2R)-顺式-4-环己烯-1,2-二羧酸 1-单甲酯; (1S,2R)-1-甲基 顺式-1,2,3,6-四氢邻苯二甲酸酯; (1S,2R)-顺式-4-环己烯-1,2-二羧酸 1-单甲酯

Database IDs

• CAS Number: 88335-93-7
• EC Number: 000-000-0
• MDL Number: MFCD00075490
• Beilstein Number: 5262096
• PubChem SID: 24888903; 162245575; 24862738
• PubChem CID: 5325907

CALCULATED PROPERTIES

• Acid pKa: 4.230265
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.39321166
• LogD (pH = 7.4): -2.1157634
• Log P: 0.8968734
• Molar Refractivity: 45.9715 cm^3
• Polarizability: 17.69615 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 64-67°C; 65-67 °C(lit.)
• Optical Rotation: [α]20/D +11.5±1°, c = 1% in acetone; [α]20/D +13°, c = 1 in acetone

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (sum of enantiomers, HPLC); 97%; 98%
• Linear Formula: HO2CC6H8CO2CH3

DETAILS

Sigma Aldrich - 87462

Other Notes
Chiral building block used for the synthesis of chiral cyclohexane compounds, e.g. carbapenems1; Pheromones2; etc.3,4
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 367281

Packaging
250 mg in glass bottle