CAS 2564-83-2|TEMPO|ol|1-Oxy-2,2,6,6-tetramethylpiperidine, free radical|ump 5'-end residue|TEMPO|tyrosine(.)|(2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl|2,2,6,6-Tetramethyl-1-piperidinyloxy, free radi...

基本信息

化学结构

分子式

C₉H₁₈NO

分子量

156.24532

精确质量

156.1388392

电荷

InChI

InChI=1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3

InChIKey

QYTDEUPAUMOIOP-UHFFFAOYSA-N

Canonic Smiles

[O]N1C(C)(C)CCCC1(C)C

Isomeric Smiles

N1(C(CCCC1(C)C)(C)C)[O]

计算属性

JChem

LogD (pH = 7.4)

1.75

LogD (pH = 5.5)

1.75

Log P

1.75

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

0.71

极化表面积

3.24

极化性

18.42

摩尔折射率

45.59

LOG S

-1.91

数据来源

名称和标识

别名

TEMPO1-Oxy-2,2,6,6-tetramethylpiperidine, free radicalTEMPO(2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl2,2,6,6-四甲基哌啶氧化物2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical2,2,6,6-四甲基哌啶-1-氧自由基2,2,6,6-Tetramethylpiperidine 1-oxylTEMPO2,2,6,6-Tetramethylpiperidine 1-Oxyl2,2,6,6-四甲基哌啶氧化物, 自由基2,2,6,6-四甲基哌啶氧化物2,2,6,6-Tetramethylpiperidine 1-oxylTEMPO, free radical1,1,5,5-tetramethylpentamethylene nitroxideTEMPO2,2,6,6-tetramethyl-1-piperidinyloxy2,2,6,6-tetramethylpiperidinooxy radical

IUPAC标准名

ol (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl

IUPAC传统名

ump 5'-end residue tyrosine(.) tanan

名称和标识

数据登录号

化合物性质

安全信息

Corrosive/Keep Cold

S26 36/37/39 45

26-36/37/39-45

26-36/37/39-45-60

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

Wikipedia

TEMPO

Sigma Aldrich

426369

Application
稳定的氮氧自由基，用于控制活性聚合反应
General description
想了解 Karen Wooley 教授提供的采用 NMP 引发剂的合成方案，请访问技术聚焦。
包装
1, 5 g in glass bottle

214000

Application
用于将橙花醇经碘苯二乙酸氧化为橙花醛的催化氧化剂。1
General description
铜/TEMPO 已用于将伯醇催化氧化为醛。2
包装
1, 5, 25 g in glass bottle

87903

Other Notes
稳定的自由基，用于自由基捕捉机理研究；TEMPO 优先与以碳为中心的自由基反应1,2,3；催化剂，用于通过 NaOCl 将伯醇氧化为醛4

ChEBI

CHEBI:32849

A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.

描述信息

参考文献

PubChem文献

数据源提供

• For a review of the use of stable nitroxyl radicals for the oxidation of primary and secondary alcohols, see: Synthesis, 1153 (1996).

• Cf also 4-Hydroxy-TEMPO, A12497, and 4-Acetamido-TEMPO, B23456.

• The addition of quaternary salts to the reaction mixture permits further oxidation of aldehydes to acids. Selective oxidation of a primary OH to an aldehyde can be achieved in the presence of a secondary OH: J. Org. Chem., 54, 2970 (1989); Tetrahedron Lett., 31, 2177 (1990). The oxidation can also be performed using NCS under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996), with Iodosobenzene diacetate, B24531: J. Org. Chem., 62, 6974 (1997), or Trichloroisocyanuric acid, B23906: Org. Lett., 3, 3041 (2001).

• For brief features on TEMPO and related reagents, see: Synlett, 563 (2001); 1757 (2003); 657 (2006). For reviews on nitroxide radicals, see: Synthesis, 190, 401 (1971); Chem. Rev., 78, 37 (1978); J. Sci. Ind. Res., 54, 623 (1995).

• In the presence of a catalytic amount of KBr, catalyzes the selective oxidation of primary and secondary alcohols to aldehydes and ketones by buffered NaOCl: J. Org. Chem., 50, 4888 (1985); 52, 2559 (1987); Org. Synth. Coll., 8, 367 (1993). High yields of aldehydes can also be obtained under mild, phase-transfer conditions with Oxone.: Org. Lett., 2, 1173 (2000). In the presence of CuCl, aerobic oxidation of alcohols to aldehydes and ketones has been accomplished in the ionic liquid 1-n-Butyl-3-methylimidazolium hexafluorophosphate, L19086: Org. Lett., 4, 1507 (2002). With NaOCl, ɑ-amino or ɑ-alkoxy alcohols have also been oxidized to the aldehydes: Tetrahedron Lett., 33, 5029 (1992). The use of I₂ as cooxidant is useful for sensitive substrates: Org. Lett., 5, 235 (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

ol (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl

IUPAC传统名

ump 5'-end residue tyrosine(.) tanan

描述信息

Wikipedia

TEMPO

Sigma Aldrich

426369

214000

Application
用于将橙花醇经碘苯二乙酸氧化为橙花醛的催化氧化剂。1
General description
铜/TEMPO 已用于将伯醇催化氧化为醛。2
包装
1, 5, 25 g in glass bottle

87903

Other Notes
稳定的自由基，用于自由基捕捉机理研究；TEMPO 优先与以碳为中心的自由基反应1,2,3；催化剂，用于通过 NaOCl 将伯醇氧化为醛4

ChEBI

CHEBI:32849

A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.

参考文献

PubChem文献

数据源提供

• For a review of the use of stable nitroxyl radicals for the oxidation of primary and secondary alcohols, see: Synthesis, 1153 (1996).

• Cf also 4-Hydroxy-TEMPO, A12497, and 4-Acetamido-TEMPO, B23456.

生物活性

PubChem BioAssay

化合物性质

安全信息

Corrosive/Keep Cold

S26 36/37/39 45

26-36/37/39-45

26-36/37/39-45-60

化合物信息

ID:90333