diphenyl-2H-5λ6-thieno[3,4-d][1,3]dioxole-2,5,5-trione

• ChemBase编号: 302349
• 分子式: C17H10O5S
• 平均质量: 326.3233
• 单一同位素质量: 326.02489442
• SMILES: c1ccc(cc1)C1=c2c(=C(S1(=O)=O)c1ccccc1)oc(=O)o2
• Canonical SMILES: O=c1oc2=C(c3ccccc3)S(=O)(=O)C(=c2o1)c1ccccc1
• InChI: InChI=1S/C17H10O5S/c18-17-21-13-14(22-17)16(12-9-5-2-6-10-12)23(19,20)15(13)11-7-3-1-4-8-11/h1-10H
• InChIKey: UEOYFCIGZWQXTP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: diphenyl-2H-5λ^6-thieno[3,4-d][1,3]dioxole-2,5,5-trione
• IUPAC传统名: diphenyl-5λ^6-thieno[3,4-d][1,3]dioxole-2,5,5-trione
• 别名: 4,6-二苯基噻吩[3,4-d]-1,3-二氧-2-酮-5,5-二氧; Steglich's Reagent; TDO activated carbonate; 4,6-Diphenylthieno[3,4-d]-1,3-dioxol-2-one 5,5-dioxide

登记号

• CAS号: 54714-11-3
• EC号: 259-301-2
• MDL号: MFCD00040564
• Beilstein号: 1396884

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 2.6422966
• LogD (pH = 7.4): 2.6422966
• Log P: 2.6422966
• 摩尔折射率: 85.4268 cm^3
• 极化性: 32.958214 Å^3
• 极化表面积: 69.67 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 224-230°C

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 危险公开号: 36/37/38
• 安全公开号: 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A

产品相关信息

• 纯度: 97%

参考文献

• Reagent for the formation of active esters for peptide coupling or esterification. In the presence of 1 equiv. of base, these enolize with formation of a deep red anion in which the enolate oxygen is well placed to facilitate aminolysis or alcoholysis: Angew. Chem. Int. Ed., 15, 444 (1976). Aminolysis occurs more rapidly in dichloromethane than in the more polar DMF. Progress of acylation can readily be followed by disappearance of the red color of the active ester, giving scope for the possibility of automatic monitoring of the reaction: J. Chem. Soc., Chem. Commun., 1870 (1987).
• Reacts with t-butanol and pyridine to give an activated reagent for the formation of Boc derivatives of amino acids which can then further react with the reagent to form active esters for peptide coupling: Angew. Chem. Int. Ed., 18, 307 (1979); Liebigs Ann. Chem., 437 (1988). For peptide reagents, see Appendix 6.