(1,1-dioxo-1λ?-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate

• ChemBase编号: 134452
• 分子式: C14H11NO7S
• 平均质量: 337.30464
• 单一同位素质量: 337.0256227
• SMILES: c1ccc2c(c1)C=C(S2(=O)=O)COC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)OCC1=Cc2c(S1(=O)=O)cccc2
• InChI: InChI=1S/C14H11NO7S/c16-12-5-6-13(17)15(12)22-14(18)21-8-10-7-9-3-1-2-4-11(9)23(10,19)20/h1-4,7H,5-6,8H2
• InChIKey: XBVMGLSMCWWRLS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (1,1-dioxo-1λ?-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate; (1,1-dioxo-1λ^6-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate
• IUPAC传统名: (1,1-dioxo-1λ?-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate; (1,1-dioxo-1λ^6-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate
• 别名: (1,1-二氧-苯并噻吩-2-甲基) 丁二酸亚胺基 甲酸酯; (1,1-二氧-苯并噻吩-2-甲基)丁二酸亚胺基甲酸酯; 1,1-二杂苯[B]硫代苯甲基 N-琥珀酸胺碳酸盐; Carbonic acid, (1,1-dioxidobenzo[b]thien-2-yl)methyl 2,5-dioxo-1-pyrrolidinyl ester; N-(Benzo[b]thiophenesulfone-2-methoxycarbonyl)succinimide; 1,1-Dioxobenzo[b]thiophen-2-ylmethyl N-succimidyl carbonate; Bsmoc-OSu; N-(Benzo[b]thiophenesulfone-2-methoxycarbonyloxy)succinimide; 1,1-Dioxobenzo[b]thiophen-2-ylmethyl N-succinimidyl carbonate

登记号

• CAS号: 197244-91-0
• MDL号: MFCD03095506
• Beilstein号: 8274967
• PubChem SID: 162228728; 24857579
• PubChem CID: 3344958

理论计算性质

• Acid pKa: 17.63414
• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): 0.71422684
• LogD (pH = 7.4): 0.71422684
• Log P: 0.71422684
• 摩尔折射率: 77.1379 cm^3
• 极化性: 30.528145 Å^3
• 极化表面积: 107.05 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: ~165 °C (dec.); 140°C dec.

安全信息

• 保存注意事项: Moisture Sensitive
• 德国WGK号: 3
• TSCA收录: 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥97.0%; 95%; min 98%
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C14H11NO7S

详细说明

Sigma Aldrich - 29237

Other Notes
肽偶联反应中的新型碱和亲核试剂敏感型氨基保护基团，对碱的稳定性低于芴甲氧羰基，用三(2-氨基乙基)胺 (TAEA) 处理可去保护1

参考文献

• Reagent introduced by Carpino for protection of amino acids as their benzothiophenesulfone-2-methoxycarbonyl (Bsmoc) derivatives (see 1,1-Dioxobenzo[b]thiophen-2-ylmethyl chloroformate, L19559): J. Am. Chem. Soc., 119, 9915 (1997); J. Org. Chem., 64, 4324 (1999).