1,4-dimethyl but-2-ynedioate

• ChemBase编号: 78495
• 分子式: C6H6O4
• 平均质量: 142.10944
• 单一同位素质量: 142.02660867
• SMILES: O(C(=O)C#CC(=O)OC)C
• Canonical SMILES: COC(=O)C#CC(=O)OC
• InChI: InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
• InChIKey: VHILMKFSCRWWIJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,4-dimethyl but-2-ynedioate
• IUPAC传统名: 1,4-dimethyl but-2-ynedioate
• 别名: 丁炔二酸二甲酯; Dimethyl 2-butynedioate; Dimethyl acetylenedicarboxylate; DMAD; Acetylenedicarboxylic; acid dimethyl ester; Dimethyl acetylenedicarboxylate; Acetylenedicarboxylic acid dimethyl ester; Butynedioic acid dimethyl ester; Dimethyl acetylenedicarboxylate; Dimethyl but-2-yne-1,4-dioate; dimethyl but-2-ynedioate

登记号

• CAS号: 762-42-5; 10227-18-6
• EC号: 212-098-4
• MDL号: MFCD00008456
• Beilstein号: 607063
• PubChem SID: 162043261; 24845139; 24893421
• PubChem CID: 12980
• Chemspider ID: 12440
• 维基百科标题: Dimethyl_acetylenedicarboxylate

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.9685472
• LogD (pH = 7.4): 0.9685472
• Log P: 0.9685472
• 摩尔折射率: 32.5402 cm^3
• 极化性: 12.367345 Å^3
• 极化表面积: 52.6 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Insoluble in water; Soluble in most; organic solvents
• 外观: Colorless liquid
• 熔点: -18 - -16°C; -18°C; -18°C; c
• 沸点: 195–198 °C; 96–98° at 8 mm Hg; 195-198°C; 95-98 °C/19 mmHg(lit.); 95-98°C/19mm
• 闪点: 186.8 °F; 187 °F; 86 °C; 86°C; 86°C(186°F)
• 密度: 1.156; 1.156 g/mL at 25 °C(lit.); 1.1564 g/cm3
• 折射率: 1.447; 1.4470; 1.4480; n20/D 1.447; n20/D 1.447(lit.)
• 疏水性(logP): -0.09

安全信息

• 保存注意事项: Corrosive/Harmful/Air Sensitive/Light Sensitive/Lachrymatory/Keep Cold/Store under Argon; Light Sensitive
• RTECS编号: ES0175000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); X
• 联合国危险货物编号: 3265; UN1760
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 21/22-34; 34; R34
• 安全公开号: 23-26-27-36/37/39-45; 26-36/37/39-45; S23 S26 S27; S36/37/39 S45
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• 主要危害: Toxic gas
• GHS危险声明: H302-H314; H314-H318-H302-H227
• GHS警示性声明: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2

产品相关信息

• 纯度: ≥96.0% (GC); 95%; 97%; 98%; 99%
• 级别: purum
• 线性分子式: CH3OCOC≡CCO2CH3

详细说明

Sigma Aldrich - D138401

包装
5, 25 g in glass bottle
Application
用于 Diels-Alder 反应的多功能亲二烯体。1,2,3

参考文献

• Dienophile in Diels-Alder and related reactions. For addition to a bis-allene, followed by dimerization to a paracyclophane, see: Org. Synth. Coll., 7, 485 (1990).
• For use in the masking of double bonds for subsequent release by cycloreversion, see: J. Org. Chem., 44, 962 (1979). Review of cycloreversion reactions in organic synthesis: Synthesis, 121 (1985).
• Used in synthesis of a wide variety of heterocyclic systems including benzo[b]thiophenes from thiophenols: Acta Chem. Scand.,27, 595 (1973), and chromones from phenols: Austral. J. Chem., 48, 677 (1995):
  
• Stabilized anions derived from cyclic ?-keto phosphonates undergo ring expansion, via a tandem Michael-Aldol-fragmentation mechanism, to give phosphonates with an additional two carbons in the ring, thus providing a route to highly functionalized medium ring compounds: J. Org. Chem., 60, 3084 (1995):
  
• Reacts with activated carbonyl compounds, such as ɑ-keto esters or ɑ-keto nitriles, in the presence of triphenylphosphine, to give highly functionalized -butyrolactones: J. Org. Chem., 61, 4516 (1996). For a further example with reaction scheme, see 2,2,2-Trifluoroacetophenone, A11403.