ethyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate

• ChemBase ID: 145431
• Molecular Formular: C10H16O4
• Molecular Mass: 200.23164
• Monoisotopic Mass: 200.10485899
• SMILES: CCOC(=O)/C=C/[C@H]1COC(O1)(C)C
• Canonical SMILES: CCOC(=O)/C=C/[C@H]1COC(O1)(C)C
• InChI: InChI=1S/C10H16O4/c1-4-12-9(11)6-5-8-7-13-10(2,3)14-8/h5-6,8H,4,7H2,1-3H3/b6-5+/t8-/m0/s1
• InChIKey: GZVXALXOWVXZLH-GJIOHYHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• IUPAC Traditional name: ethyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• Synonyms: Ethyl (S)-trans-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate; Ethyl (S)-trans-4,5-O-isopropylidene-4,5-dihydroxy-2-pentenoate; Ethyl (S)-(+)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-propenoate,predominantly trans; Ethyl (S)-trans-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate; (S)-反式-3-(2,2-二甲基-1,3-二氧杂环戊烷-4-基)丙烯酸乙酯; (S)-反式-4,5-O-异亚丙基-4,5-二羟基-2-戊烯酸乙酯; (S)-(+)-3-(2,2-二甲基-1,3-二氧杂环戊烷-4-基)-2-丙烯酸乙酯，主要为反式; (S)-反式-3-(2,2-二甲基-1,3-二氧杂环戊烷-4-基)丙烯酸乙酯

Database IDs

• CAS Number: 64520-58-7
• MDL Number: MFCD00075367
• Beilstein Number: 4231890
• PubChem SID: 24861444; 162239637
• PubChem CID: 6364657

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.4469361
• LogD (pH = 7.4): 1.4469361
• Log P: 1.4469361
• Molar Refractivity: 52.4268 cm^3
• Polarizability: 20.370234 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 115-117 °C/12 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1.035 g/mL at 25 °C(lit.); 1.049 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.4505(lit.); n20/D 1.453
• Optical Rotation: [α]20/D +41±2°, c = 1% in chloroform; [α]20/D +44°, c = 0.5 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C10H16O4

DETAILS

Sigma Aldrich - 346810

Packaging
5 g in glass bottle

Sigma Aldrich - 59434

Other Notes
Chiral building block; olefin cyclopropanation 1; Stereoselective [3+2]- and [4+2]-cycloadditions2; Reduction to an allylic alcohol 3