N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide

• ChemBase编号: 89999
• 分子式: C10H18N2O4
• 平均质量: 230.26092
• 单一同位素质量: 230.12665707
• SMILES: O(C(=O)/N=N/C(=O)OC(C)(C)C)C(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)/N=N/C(=O)OC(C)(C)C
• InChI: InChI=1S/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3
• InChIKey: QKSQWQOAUQFORH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide; (E)-N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide
• IUPAC传统名: N-[(tert-butoxycarbonyl)imino](tert-butoxy)formamide; (E)-N-[(tert-butoxycarbonyl)imino](tert-butoxy)formamide
• 别名: 偶氮二甲酸二叔丁酯; 偶氮二羧酸二叔丁酯; Di-tert-butyl azodicarboxylate 98%; Bis(1,1-dimethylethyl)azodicarboxylate; DBAD; Di-tert-butyl azodiformate; NSC 109889; Di-tert-butyl azodicarboxylate; Azodicarboxylic acid di-tert-butyl ester; DTAD; Di-tert-butyl diazene-1,2-dicarboxylate

登记号

• CAS号: 870-50-8
• EC号: 212-796-9
• MDL号: MFCD00015001
• Beilstein号: 1911434
• PubChem SID: 162076854; 24848251
• PubChem CID: 6034084

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 2.1676028
• LogD (pH = 7.4): 2.1676028
• Log P: 2.1676028
• 摩尔折射率: 56.5902 cm^3
• 极化性: 22.475769 Å^3
• 极化表面积: 77.32 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

• 熔点: 89-92 °C; 89-92 °C(lit.); 89-92°C; 89-92°C

安全信息

• 保存注意事项: Irritant/Light Sensitive/Keep Cold/Store under Argon; Light Sensitive
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (GC); 98%
• 级别: purum
• 线性分子式: (CH3)3COCON=NCOOC(CH3)3

详细说明

Sigma Aldrich - D1516

Application
Reactant for:
• Preparation of hexapeptide key fragments via stereoselective selenocyclization/oxidative deselenylation or hydrazination/cyclization reactions1
• Asymmetric Michael addition reactions2
• Preparation of dipeptidyl peptidase IV dependent water-soluble prodrugs via Mitsunobu reaction3
• Synthesis of pyrroloisoquinoline template via stereoselective N-acyliminium-mediated cyclization and enolate amination for synthesis of peptidomimetic compounds4
• Barbier-type propargylation reactions5
• Synthesis of bacterial peptide deformylase (PDF) inhibitor fumimycin6
• Asymmetric amination of glycine Schiff bases7

Sigma Aldrich - 135992

Application
用于以轴向手性胍催化 β 酮酯亲电氨基化的试剂。8用作以 L-脯氨酸或 (S)-2-吡咯烷基四唑这类有机催化剂催化进行的 3,6-二氢哒嗪的对映选择性合成的结构单元。9
用于通过手性有机催化剂催化进行的非对称 Friedel-Crafts 胺化。
Reactant for:
• Preparation of hexapeptide key fragments via stereoselective selenocyclization/oxidative deselenylation or hydrazination/cyclization reactions1
• Asymmetric Michael addition reactions2
• Preparation of dipeptidyl peptidase IV dependent water-soluble prodrugs via Mitsunobu reaction3
• Synthesis of pyrroloisoquinoline template via stereoselective N-acyliminium-mediated cyclization and enolate amination for synthesis of peptidomimetic compounds4
• Barbier-type propargylation reactions5
• Synthesis of bacterial peptide deformylase (PDF) inhibitor fumimycin6
• Asymmetric amination of glycine Schiff bases7
包装
5, 25 g in glass bottle

Sigma Aldrich - 11625

Other Notes
酸不稳定试剂，用于温和分离产品的 Mitsunobu 反应8；烯醇化物和烷基锂的亲电氨基化和肼化反应9,10,11
Application
Reactant for:
• Preparation of hexapeptide key fragments via stereoselective selenocyclization/oxidative deselenylation or hydrazination/cyclization reactions1
• Asymmetric Michael addition reactions2
• Preparation of dipeptidyl peptidase IV dependent water-soluble prodrugs via Mitsunobu reaction3
• Synthesis of pyrroloisoquinoline template via stereoselective N-acyliminium-mediated cyclization and enolate amination for synthesis of peptidomimetic compounds4
• Barbier-type propargylation reactions5
• Synthesis of bacterial peptide deformylase (PDF) inhibitor fumimycin6
• Asymmetric amination of glycine Schiff bases7

参考文献

• Aza-dienophile. The ester groups are readily removed from adducts by acid: J. Org. Chem., 26, 4336 (1961); 38, 2043 (1973); 40, 563 (1975).
• Useful "NH₂⁺" synthon for enantioselective amination reactions: J. Am. Chem. Soc., 108, 6394, 6395, 6397 (1986); Tetrahedron Lett., 29, 6765 (1988).
• Mitsunobu reaction with alcohols gives a direct route to the corresponding N,N'-di-Boc protected hydrazine derivatives: Tetrahedron Lett., 37, 4327 (1996).