N-[(piperidine-1-carbonyl)imino]piperidine-1-carboxamide

• ChemBase编号: 151260
• 分子式: C12H20N4O2
• 平均质量: 252.3128
• 单一同位素质量: 252.1586259
• SMILES: C1CCN(CC1)C(=O)/N=N/C(=O)N1CCCCC1
• Canonical SMILES: O=C(N1CCCCC1)/N=N/C(=O)N1CCCCC1
• InChI: InChI=1S/C12H20N4O2/c17-11(15-7-3-1-4-8-15)13-14-12(18)16-9-5-2-6-10-16/h1-10H2
• InChIKey: OQJBFFCUFALWQL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-[(piperidine-1-carbonyl)imino]piperidine-1-carboxamide; (NE)-N-{[(E)-piperidine-1-carbonyl]imino}piperidine-1-carboxamide
• IUPAC传统名: N-(piperidine-1-carbonylimino)piperidine-1-carboxamide; (NE)-N-[(E)-piperidine-1-carbonylimino]piperidine-1-carboxamide
• 别名: 偶氮二甲酰二哌啶; 1,1'-(偶氮二羰基)二哌啶; 1,1'-(偶氮二羰基)二哌啶; 偶氮二甲酰二哌啶; 1,1′-Azobis(N,N-pentamethyleneformamide); ADD; NSC 356027; SR 4077; Azodicarboxylic acid dipiperidide; 1,1′-(Azodicarbonyl)dipiperidine; 1,1-(azodicarbonyl)dipiperidine; 1,1'-(Azodicarbonyl)dipiperidine; 1,1'-(Azodicarbonyl)dipiperidine; ADDP; Azodicarboxylic dipiperidide; Azodicarboxylic acid dipiperidide

登记号

• CAS号: 10465-81-3
• MDL号: MFCD00010111
• Beilstein号: 261917
• PubChem SID: 162245416; 24847283; 24855495
• PubChem CID: 5702657

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 0.74944675
• LogD (pH = 7.4): 0.74944675
• Log P: 0.74944675
• 摩尔折射率: 66.956 cm^3
• 极化性: 25.547024 Å^3
• 极化表面积: 65.34 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: 132-136 °C(lit.); 133-136°C; 134-136 °C(lit.)

安全信息

• 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

产品相关信息

• 纯度: ≥98.5% (TLC); 97%; 99%
• 级别: purum
• Empirical Formula (Hill Notation): C12H20N4O2

详细说明

Sigma Aldrich - 255920

Application
广泛用于 Mitsunobu 反应的试剂
用于研究芳基硼酸通过铜催化加成得到偶氮二甲酸衍生物，从而生成芳基取代酰肼的反应。10
Reactant for preparation of:
• Polyfluoroalkylated tripyrazolylmethane ligands1
• (-)-Hygromycin A via Mitsunobu glycosylation2
• Optically active α,α-disubstituted amino acids via Mitsunobu reaction3
• Aza-β-lactams through [2+2] cycloaddition reactions4
• Glycosyl disulfides5
• Pyridine ether PPAR agonists6
• S-glycosyl amino acid building blocks for combinatorial neoglycopeptide synthesis7
• Histamine H3 receptor antagonists8Reactant for:
• Mitsunobu inversion reactions9
包装
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 11632

Other Notes
在高 pK 值酸的 Mitsunobu 反应中引入的试剂；过量的试剂和反应产物通过过滤即可去除（用己烷稀释后）1,2

参考文献

• Reagent for the Mitsunobu reaction (see Diethyl azodicarboxylate, L19348), used in combination with tri-n-butylphosphine as a more powerful system than DEAD for higher pK_a nucleophiles: Tetrahedon Lett., 34, 1639 (1993); Tetrahedron, 61, 6218 (2005). Has also been utilized in a selective method for converting primary and secondary alcohols to carbonyl compounds, by reaction of the alcohol with a Grignard reagent, followed by oxidation of the intermediate magnesio-derivative with ADDP: J. Org. Chem., 38, 1652 (1973); Bull. Chem. Soc. Jpn., 2773 (1977).