戴斯-马丁试剂

• 产品号: L15779
• CAS号: 87413-09-0
• 分子式: C13H13IO8
• 分子量: 424.14199

产品别名

• 标题: Dess-Martin periodinane
• IUPAC标准名: 1,1-bis(acetyloxy)-3-oxo-3H-1λ^5,2-benziodaoxol-1-yl acetate
• IUPAC传统名: dess-martin periodinane
• 别名: DMP; 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one

产品登记号

• 默克索引号: 142933
• MDL号: MFCD00130127
• CAS号: 87413-09-0
• Beilstein号: 4548207

产品性质

• 熔点: 130-132°C dec.
• GHS危险声明: H272-H315-H319-H335
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 欧盟危险性物质标志: 氧化性(Oxidising) (O)
• GHS警示性声明: P221-P210-P305+P351+P338-P302+P352-P405-P501A
• 危险公开号: 8-36/37/38-44
• 安全公开号: 17-26-37
• 保存注意事项: Moisture & Light Sensitive
• TSCA收录: 否
• 联合国危险货物等级: 5.1
• 联合国危险货物编号: UN1479
• 联合国危险货物包装类别(PG): III

参考文献

• One of the mildest reagents for the selective oxidation of primary and secondary alcohols to aldehydes and ketones. High yields can be obtained at ambient temperatures, under neutral conditions, in chloroform, dichloromethane or acetonitrile: J. Org. Chem., 48, 4155 (1983); J. Am. Chem. Soc., 113, 7277 (1991); (reviews): J. Prakt. Chem./Chem. Ztg., 338, 588 (1996); Synlett, 278 (2000). Has been employed for the oxidation of a wide variety of sensitive substrates and is particularly valuable in multi-step syntheses of polyfunctional molecules with complex stereochemistry. For an example involving exclusive oxidation of one of four possible secondary OH groups in a synthesis of erythromycin B, see: J. Am. Chem. Soc., 119, 3193 (1997). Allylic and benzylic alcohols can be oxidized selectively in the presence of saturated alcohols, and give the carbonyl compounds cleanly without over-oxidation or cis-trans isomerization: Tetrahedron Lett., 29, 995 (1988); J. Org. Chem., 55, 1636 (1990).
• CAUTION! In the presence of moisture, may form iodoxybenzoic acid which has been reported to be explosive under excessive heating or impact: Chem. Eng. News, 68(29), 3 (1990).
• For a detailed discussion of the scope and advantages of this reagent, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 4982.
• Hydroxamic acids are oxidized to acyl nitroso compounds which can undergo cycloaddition to dienes: Synth. Commun., 30, 47 (2000).
• Has also been used for deoximation of ketoximes to ketones under mild conditions: Tetrahedron Lett., 39, 3209 (1998); Synthesis, 760 (1999).
• For use in the synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles, by oxidation of amides and amines, see: Angew. Chem. Int. Ed., 44, 5992 (2005).
• Deprotection of thioacetals can be accomplished under extremely mild conditions: Org. Lett., 5, 575 (2003).
• ɑ,?-Unsaturated carboxylic acids undergo Hunsdiecker-type decaboxylative bromination with tetraethylammonium bromide in the presence of the reagent: Synlett, 2495 (2005).