1,1-bis(acetyloxy)-3-oxo-3H-1$l^{5},2-benziodaoxol-1-yl acetate

• ChemBase编号: 70652
• 分子式: C13H13IO8
• 平均质量: 424.14199
• 单一同位素质量: 423.96551538
• SMILES: [I]1(OC(=O)c2c1cccc2)(OC(=O)C)(OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[I]1(OC(=O)C)(OC(=O)C)OC(=O)c2c1cccc2
• InChI: InChI=1S/C13H13IO8/c1-8(15)19-14(20-9(2)16,21-10(3)17)12-7-5-4-6-11(12)13(18)22-14/h4-7H,1-3H3
• InChIKey: NKLCNNUWBJBICK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,1-bis(acetyloxy)-3-oxo-3H-1$l^{5},2-benziodaoxol-1-yl acetate; 1,1-bis(acetyloxy)-3-oxo-3H-1λ^5,2-benziodaoxol-1-yl acetate
• IUPAC传统名: dess-martin periodinane; dess–martin periodinane
• 别名: 1,1,1-三(乙酰氧基)-1,1-二氢-1,2-苯碘酰-3-(1H)-酮; 戴斯-马丁氧化剂; 戴斯-马丁试剂; 戴斯-马丁氧化剂 溶液; 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one; Dess–Martin periodinane; Dess–Martin periodinane; 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one; Dess-Martin periodinane; DMP; 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; Dess-Martin periodinane solution; 1,1-Dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one; Dess-Martin periodinane

登记号

• CAS号: 87413-09-0
• MDL号: MFCD00130127
• Beilstein号: 4548207
• 默克索引号: 142933
• PubChem SID: 162036367; 24879825; 24856593
• PubChem CID: 159087
• Chemspider ID: 139925
• 维基百科标题: Dess–Martin_periodinane

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 1.898416
• LogD (pH = 7.4): 1.898416
• Log P: 1.898416
• 摩尔折射率: 80.292 cm^3
• 极化性: 33.54322 Å^3
• 极化表面积: 105.2 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: white powder, chips,; crystals or crystalline; powder and/or chunks
• 熔点: 103 – 133 °C; 130-132°C dec.; 130-133 °C(lit.); 130-133°C
• 沸点: 40 °C
• 密度: 1.362 g/cm^3 solid; 1.369 g/mL at 25 °C

安全信息

• 保存注意事项: IRRITANT; Moisture & Light Sensitive; Oxidising Agent/Harmful/Irritant/Air Sensitive/Moisture Sensitive/Store under Argon/Keep Cold
• 欧盟危险性物质标志: 氧化性(Oxidising) (O); 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1593; UN1479
• 德国WGK号: 3
• 联合国危险货物等级: 5.1; 6.1
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 40-44; 8-20/21/22-36/37/38-44; 8-36/37/38-44
• 安全公开号: 17-26-37; 26-36; 36/37
• TSCA收录: false; 否
• GHS危险品标识: GHS03; GHS06; GHS07; GHS08
• GHS警示词: Danger; Warning
• GHS危险声明: H272-H302-H312-H315-H319-H332-H335; H272-H315-H319-H335; H315-H319-H331-H351
• GHS警示性声明: P220-P261-P280-P305 + P351 + P338; P221-P210-P305+P351+P338-P302+P352-P405-P501A; P261-P281-P305 + P351 + P338-P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1593 6.1/PG 3
• 欧盟补充危害声明: Risk of explosion if heated under confinement.
• 保存温度: -20°C; 2-8°C

产品相关信息

• 纯度: 95+%; 97%; 98%
• 浓度: 0.3 M in methylene chloride
• Empirical Formula (Hill Notation): C13H13IO8

详细说明

Sigma Aldrich - 274623

Application
用于将 1° 和 2° 醇氧化为醛和酮的氧化剂。1,2
用于将羟基二氢卟酚氧化为二氢卟酚-α-二酮和四酮。
包装
1, 5, 25, 50, 250 g in glass bottle

Sigma Aldrich - 559873

Application
广泛用于将醇轻度氧化为醛和酮的试剂。1
包装
5, 25 mL in glass bottle

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).