CAS 2446-83-5|Diisopropyl azodicarboxylate|DIAD|偶氮二甲酸二异丙酯|N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide|Azodicarboxylic acid diisopropyl ester|diisopropyl azodicarboxylate|Di...

基本信息

化学结构

分子式

C₈H₁₄N₂O₄

分子量

202.20776

精确质量

202.09535694

电荷

InChI

InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3

InChIKey

VVWRJUBEIPHGQF-UHFFFAOYSA-N

Canonic Smiles

CC(OC(=O)/N=N/C(=O)OC(C)C)C

Isomeric Smiles

N(=N\C(=O)OC(C)C)/C(=O)OC(C)C

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

1.6064495

LogD (pH = 7.4)

1.6064495

Log P

1.6064495

摩尔折射率

47.3138

极化性

18.836767

极化表面积

77.32

可自由旋转的化学键

里宾斯基五规则

true

数据来源

名称和标识

别名

Diisopropyl azodicarboxylateDIAD偶氮二甲酸二异丙酯Azodicarboxylic acid diisopropyl esterDiisopropyl azodicarboxylateDiisopropyl azodiformateDiisopropyl diazene-1,2-dicarboxylateDiprop-2-yl diazene-1,2-dicarboxylateBis(isopropyl) azodicarboxylate 96%

IUPAC标准名

N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide (E)-N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide

IUPAC传统名

diisopropyl azodicarboxylate N-[(isopropoxycarbonyl)imino]isopropoxyformamide

名称和标识

数据登录号

MDL号

MFCD00008875

EC号

219-502-8

Beilstein号

1912326

PubChem SID

2484727624853505162039282

CAS号

2446-83-5

维基百科标题

Diisopropyl_azodicarboxylate

Chemspider ID

4515532

PubChem CID

5363146

数据登录号

化合物性质

安全信息

Harmful/Irritant/Keep Cold/Store under Argon

Light Sensitive

S16,S26,S29,S36,S37,S39,S47,S61

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

Wikipedia

Diisopropyl_azodicarboxylate

Apollo Scientific

OR0923

Alternative to DEAD

Sigma Aldrich

225541

General description
在铁催化剂催化下与二氧磷杂环己烷反应生成重排膦叶立德产物。8
包装
25, 100 g in poly bottle
5 g in glass bottle
Application
Reactant for preparation of:
• Chromenes resembling classical cannabinoids1
• MK-3281 inhibitor of the hepatitis C virus NS5B polymerase2
• Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)3
• Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties4
• Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells5
• 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists6
• Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine7

11626

Other Notes
用于 Mitsunobu 反应的试剂，综述8,9
Application
Reactant for preparation of:
• Chromenes resembling classical cannabinoids1
• MK-3281 inhibitor of the hepatitis C virus NS5B polymerase2
• Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)3
• Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties4
• Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells5
• 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists6
• Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine7

描述信息

参考文献

PubChem文献

数据源提供

• Alternative to 'DEAD' (Diethyl azodicarboxylate, L19348), more stable at elevated temperatures. DIAD has been used in combination with Triphenylphosphine, L02502, in Mitsunobu-type reactions of alcohols with acids, amides, etc. In the Mitsunobu esterification reaction yields improve with increasing acid strength. For a discussion, see: J. Org. Chem., 61, 2967 (1996).

• An extremely mild route to isocyanates involves treatment of an aliphtic primary amine with CO₂ to form the carbamate salt which reacts at low temperature with the Mitsunobu reagent from DIAD and PPh₃, giving the isocyanate in high yield. 2,6-Dialkylanilines also undergo the reaction if Bu₃P is used; the reaction failed with other anilines: Tetrahedron Lett., 40, 363 (1999).

• For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethylsilyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).

• For reviews of the Mitsunobu reaction, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996). For a brief feature on synthetic uses of Mitsunobu reagents, see: Synlett, 1221 (2003).

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC标准名

N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide (E)-N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide

IUPAC传统名

diisopropyl azodicarboxylate N-[(isopropoxycarbonyl)imino]isopropoxyformamide

数据登录号

MDL号

MFCD00008875

EC号

219-502-8

Beilstein号

1912326

PubChem SID

2484727624853505162039282

CAS号

2446-83-5

维基百科标题

Diisopropyl_azodicarboxylate

Chemspider ID

4515532

PubChem CID

5363146

描述信息

Wikipedia

Diisopropyl_azodicarboxylate

Apollo Scientific

OR0923

Alternative to DEAD

Sigma Aldrich

225541

11626

参考文献

PubChem文献

数据源提供

• For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethylsilyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).

生物活性

PubChem BioAssay

化合物性质

安全信息

Harmful/Irritant/Keep Cold/Store under Argon

Light Sensitive

S16,S26,S29,S36,S37,S39,S47,S61

化合物信息

ID:74363