2,5-dihydro-1$l^{6}-thiophene-1,1-dione

• ChemBase编号: 84968
• 分子式: C4H6O2S
• 平均质量: 118.15424
• 单一同位素质量: 118.00885043
• SMILES: S1(=O)(=O)CC=CC1
• Canonical SMILES: O=S1(=O)CC=CC1
• InChI: InChI=1S/C4H6O2S/c5-7(6)3-1-2-4-7/h1-2H,3-4H2
• InChIKey: MBDNRNMVTZADMQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,5-dihydro-1$l^{6}-thiophene-1,1-dione; 2,5-dihydro-1λ^6-thiophene-1,1-dione
• IUPAC传统名: sulfolene
• 别名: 2,5-二氢噻吩-1,1-二氧化物; 3-环丁烯砜; 丁二烯砜; 3-环丁烯砜; 环丁烯砜; 2,5-Dihydrothiophene-1,1-dioxide; Butadiene sulfone; 3-Sulfolene; Butadiene sulfone; 3-Sulfolene; Sulfolene; 2,5-dihydro-1H-1lambda~6~-thiophene-1,1-dione; 2,5-dihydrothiophene 1,1-dioxide; BUTADIENE SULFONE

登记号

• CAS号: 77-79-2
• EC号: 201-059-7
• MDL号: MFCD00005481
• Beilstein号: 107004
• 默克索引号: 148956
• PubChem SID: 24892071; 24888550; 162072084
• PubChem CID: 6498
• Chemspider ID: 6253
• 维基百科标题: Sulfolene

理论计算性质

• Acid pKa: 16.104263
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.6409026
• LogD (pH = 7.4): -0.6409026
• Log P: -0.6409026
• 摩尔折射率: 28.7166 cm^3
• 极化性: 11.343716 Å^3
• 极化表面积: 34.14 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 63-67°C; 64-67 °C; 65-66 °C; 65-66 °C(lit.)
• 闪点: 112 °C; 112°C(233°F); 233.6 °F
• 密度: 1.314

安全信息

• RTECS编号: XM9100000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 41
• 安全公开号: 26-37/39; 26-39; R
• TSCA收录: 是
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H318
• GHS警示性声明: P280-P305 + P351 + P338; P280-P305+P351+P338-P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥98.0% (GC); 98%
• 级别: purum
• Empirical Formula (Hill Notation): C4H6O2S

详细说明

MP Biomedicals - 05215718

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B84505

包装
100, 500 g in glass bottle

Sigma Aldrich - 86160

Other Notes
Diel-Alder 反应中的顺式丁二烯源1,2；二氧化硫的便利来源3

参考文献

• Convenient crystalline source of 1,3-butadiene, which is generated on heating to about 110^oC: Rec. Trav. Chim., 61, 785 (1942). For an example of its use in the Diels-Alder reaction, see: Org. Synth. Coll., 6, 454 (1988).
• Also behaves as a dienophile in with reactive dienes, for example 1,3-Diphenylisobenzofuran, L00101: J. Org. Chem., 34, 538 (1969).
• In the presence of Pd(OAc)₂, couples with aryldiazonium fluoroborates to give 3-aryl-4-sulfolenes which are readily isomerized with triethylamine to the 3-aryl-3-sulfolenes, providing a source of the corresponding 2-arylbutadienes: Synth. Commun., 26, 231 (1996).
• Lithiation occurs at the 2-position; subsequent alkylation and thermal extrusion of SO₂ gave a polyene intermediate in a synthesis of the taxane ring system: J. Org. Chem., 62, 2957 (1997).