CAS 6674-22-2|1,8-Diazabicyclo[5.4.0]undec-7-ene|1,8-diazabicycloundec-7-ene|2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine|2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine|1,8-Diazabicycloundec-7-...

基本信息

化学结构

分子式

C₉H₁₆N₂

分子量

152.23674

精确质量

152.13134852

电荷

InChI

InChI=1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2

InChIKey

GQHTUMJGOHRCHB-UHFFFAOYSA-N

Canonic Smiles

C1CCN2C(=NCCC2)CC1

Isomeric Smiles

N12CCCCCC1=NCCC2

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

-1.607904

LogD (pH = 7.4)

-1.5941415

Log P

0.80737644

摩尔折射率

46.6048

极化性

17.711895

极化表面积

15.6

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

1,8-Diazabicyclo[5.4.0]undec-7-ene2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine1,8-Diazabicycloundec-7-eneDBU,DiazabicycloundeceneDBU2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine1,8-Diazabicyclo-[5,4,0]undec-7-ene2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepineDBU solution1,8-Diazabicyclo[5.4.0]undec-7-ene solution1,8-二氮杂双环[5.4.0]十一碳-7-烯溶液1,8-Diazabicyclo[5.4.0]undec-7-eneDBU 溶液1,8-二氮杂双环[5.4.0]十一碳-7-烯2,3,4,6,7,8,9,10-八氢嘧啶并[1,2-a]氮杂卓DBU1,8-二氮双环[5.4.0]十一-7-烯

IUPAC传统名

1,8-diazabicycloundec-7-ene

IUPAC标准名

2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine

名称和标识

数据登录号

CAS号

6674-22-2

MDL号

MFCD00006930

维基百科标题

1,8-Diazabicycloundec-7-ene

PubChem SID

248602582484837316203323124860259

Chemspider ID

Beilstein号

EC号

PubChem CID

数据登录号

化合物性质

安全信息

下载链接

化合物性质

分子相关蛋白质

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分子图谱

暂无数据

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描述信息

Wikipedia

1,8-Diazabicycloundec-7-ene

Sigma Aldrich

714860

包装
100 mL in Sure/Seal™

714852

包装
100 mL in Sure/Seal™

139009

Application
卤化的 Diels-Alder 加合物使用该碱脱卤化氢，由此得到的活性 2,4-二烯酮使用 Yamamoto 试剂 (CH3Cu · BF3) 进行区域定向和立体定向 Michael 加成反应。2
用于新法合成喜树碱的 ABCD 环系统。
Features and Benefits
强位阻胺碱。
包装
25, 100, 500 g in glass bottle
Citation
应用综述。1

33482

Other Notes
脱氢卤化反应形成烯烃的脒碱1；更为重要的应用为，例如，羧酸与烷基卤的酯化反应2,3；活性亚甲基化合物的烷基化和酰化4

描述信息

参考文献

PubChem文献

数据源提供

• Widely used as a base in elimination reactions, cf 1,5-Diazabicyclo[4.3.0]non-5-ene, A13437. For use in dehydrohalogenation, see, e.g. Org. Synth. Coll., 9, 247, 663 (1998).

• For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).

• For use in the enantioselective conversion of benzylic alcohols to azides, see Diphenylphosphonic azide, A12124.

• In combination with NBS in MeOH, promotes the Hofmann rearrangement of amides to give methyl carbamates under mild conditions: J. Org. Chem., 62, 7495 (1997).

• DBU forms hydrogen-bonded complexes with carboxylic acids, which can be alkylated in good yield by alkyl bromides or iodides, in a simple esterification procedure: Bull. Chem. Soc. Jpn., 51, 2401 (1978).

• Promotes the epoxidation of ɑ?-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995).

• Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).

• Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966).

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

1,8-diazabicycloundec-7-ene

IUPAC标准名

2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine

数据登录号

CAS号

6674-22-2

MDL号

MFCD00006930

维基百科标题

1,8-Diazabicycloundec-7-ene

PubChem SID

248602582484837316203323124860259

Chemspider ID

Beilstein号

EC号

PubChem CID

描述信息

1,8-Diazabicycloundec-7-ene

Sigma Aldrich

714860

包装
100 mL in Sure/Seal™

714852

包装
100 mL in Sure/Seal™

139009

33482

Other Notes
脱氢卤化反应形成烯烃的脒碱1；更为重要的应用为，例如，羧酸与烷基卤的酯化反应2,3；活性亚甲基化合物的烷基化和酰化4

参考文献

PubChem文献

数据源提供

• Widely used as a base in elimination reactions, cf 1,5-Diazabicyclo[4.3.0]non-5-ene, A13437. For use in dehydrohalogenation, see, e.g. Org. Synth. Coll., 9, 247, 663 (1998).

• For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).

• For use in the enantioselective conversion of benzylic alcohols to azides, see Diphenylphosphonic azide, A12124.

• In combination with NBS in MeOH, promotes the Hofmann rearrangement of amides to give methyl carbamates under mild conditions: J. Org. Chem., 62, 7495 (1997).

• Promotes the epoxidation of ɑ?-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995).

• Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).

• Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966).

生物活性

PubChem BioAssay

化合物性质

安全信息

下载链接

化合物信息

ID:67496