trimethyl(oxo)-$l^{6}-sulfanylium iodide

• ChemBase编号: 85736
• 分子式: C3H9IOS
• 平均质量: 220.07243
• 单一同位素质量: 219.94188391
• SMILES: [I-].[S+](=O)(C)(C)C
• Canonical SMILES: C[S+](=O)(C)C.[I-]
• InChI: InChI=1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1
• InChIKey: BPLKQGGAXWRFOE-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: trimethyl(oxo)-$l^{6}-sulfanylium iodide; trimethyl(oxo)-λ^6-sulfanylium iodide
• IUPAC传统名: trimethyl(oxo)-$l^{6}-sulfanylium iodide; trimethyl(oxo)-λ^6-sulfanylium iodide
• 别名: 三甲基碘化亚砜; Trimethyl(oxo)sulphonium iodide; Trimethylsulphoxonium iodide; Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide; Trimethylsulfoxonium iodide; Trimethylsulfoxonium iodide

登记号

• CAS号: 1774-47-6
• EC号: 217-204-2
• MDL号: MFCD00011899
• Beilstein号: 3595854
• PubChem SID: 24900499; 162072852
• PubChem CID: 74498
• 维基百科标题: Trimethylsulfoxonium_iodide

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): -2.5195513
• LogD (pH = 7.4): -2.5195513
• Log P: -2.5195513
• 摩尔折射率: 24.539 cm^3
• 极化性: 10.235904 Å^3
• 极化表面积: 17.07 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: soluble50 mg/mL, clear
• 熔点: 208-212 °C; 208-212 °C (dec.)(lit.); 208-212(dec.)°C; ca 170°C dec.

安全信息

• 保存注意事项: Irritant/Light Sensitive; Light Sensitive
• RTECS编号: WS3585000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38
• 安全公开号: 26-37
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥97.0% (AT); 95+%; 97%; 98%; 98+%
• 级别: purum
• 线性分子式: (CH3)3S(I)O

详细说明

Sigma Aldrich - T80500

包装
25, 100, 500 g in glass bottle
Application
用强碱处理可生成内鎓盐，内鎓盐可与酮1和醛2,3的羰基发生加成反应生成环氧化物。也可优先与 α,β-不饱和酯的双键发生加成反应生成环丙酯。4,5

Sigma Aldrich - 92763

Other Notes
二甲基亚甲基氧硫鎓的前体，二甲基亚甲基氧硫鎓是多功能 C1-试剂1,2

参考文献

• Review of the chemistry of sulfonium ylides: Russ. Chem. Rev., 50, 481 (1981). Extensive review of the synthetic applications of dimethylsulfoxonium methylide: Tetrahedron, 43, 2609 (1987).
• For an example (conversion of cyclohexanone to the epoxide), see: Org. Synth. Coll., 5, 755 (1973). In contrast to Trimethylsulfonium iodide, A12639, reaction with ɑ?-unsaturated ketones occurs by 1,4-addition to give cyclopropanes: J. Am. Chem. Soc., 87, 1353 (1965):
  
• Reaction with epoxides gives oxetanes, unlike the sulfonium ylide which gives allylic alcohols: J. Org. Chem., 48, 5133 (1983); Synthesis, 1140 (1987); cf Tetrahedron Lett., 35, 5449 (1994):
  
• Similarly, N-arenesulfonylaziridines undergo ring expansion to azetidines with inversion at one carbon. Thus, cis-substituted aziridines give trans-azetidines and vice versa: Tetrahedron, 45, 1851 (1989):
  
• The ylide, generated with strong base, is a methylene transfer reagent.
• Efficient addition to enones has been effected with a highly basic system consisting of KOH in DMSO with a phase-transfer catalyst: Synth. Commun., 26, 1785 (1996).