[(1-methoxy-2-methylprop-1-en-1-yl)oxy]trimethylsilane

• ChemBase编号: 149193
• 分子式: C8H18O2Si
• 平均质量: 174.31282
• 单一同位素质量: 174.10760635
• SMILES: CC(=C(OC)O[Si](C)(C)C)C
• Canonical SMILES: COC(=C(C)C)O[Si](C)(C)C
• InChI: InChI=1S/C8H18O2Si/c1-7(2)8(9-3)10-11(4,5)6/h1-6H3
• InChIKey: JNOGVQJEBGEKMG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: [(1-methoxy-2-methylprop-1-en-1-yl)oxy]trimethylsilane
• IUPAC传统名: [(1-methoxy-2-methylprop-1-en-1-yl)oxy]trimethylsilane
• 别名: (1-甲氧基-2-甲基-1-烯丙氧基)三甲基硅烷; 1-甲氧基-2-甲基-1-(三甲基硅氧基)丙烯; 甲基三甲基硅基二甲基乙烯酮缩二乙醇; 1-甲氧基-2-甲基-1-(三甲基硅氧基)丙烯; 1-Methoxy-1-trimethylsiloxy-2-methyl-1-propene; Methyl trimethylsilyl dimethylketene acetal; MTDA; (1-Methoxy-2-methyl-1-propenyloxy)trimethylsilane; 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene; Methyl trimethylsilyl dimethylketene acetal; 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene; ((1-Methoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane

登记号

• CAS号: 31469-15-5
• EC号: 000-000-0
• MDL号: MFCD00010232
• Beilstein号: 1362893
• PubChem SID: 24883797; 24856589; 162243361
• PubChem CID: 552336

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 2.8017
• LogD (pH = 7.4): 2.8017
• Log P: 2.8017
• 摩尔折射率: 54.0646 cm^3
• 极化性: 19.539488 Å^3
• 极化表面积: 18.46 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 35 °C/15 mmHg(lit.); 35-36°C/15mm
• 闪点: 30 °C; 30°C(86°F); 86 °F
• 密度: 0.858; 0.858 g/mL at 25 °C(lit.)
• 折射率: 1.4150; n20/D 1.415(lit.); n20/D 1.416

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3271; UN1993
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 10-36/37/38
• 安全公开号: 16-26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Warning
• GHS危险声明: H226-H315-H319-H335
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3271 3/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥90% (GC); 95%; 95+%; 97%
• 级别: technical
• 线性分子式: (CH3)2C=C(OCH3)OSi(CH3)3

详细说明

Sigma Aldrich - 274585

Application
基团转移聚合反应催化剂1,2或引发剂。3用于共轭加成4和羟醛反应的多功能试剂。5,6
包装
5, 25, 100 g in glass bottle

Sigma Aldrich - 65098

Other Notes
这种重要的烯酮硅缩醛在 Lewis 酸催化下可与多种亲电试剂反应1,2,3

参考文献

• Silyl ketene acetal. The silyl enol ether of methyl isobutyrate. Catalyst for the initiation of group transfer polymerization, for controlled polymerization of ɑ?-unsaturated esters, ketones, nitriles and amides, in which the ketene acetal function is transferred along the growing polymer chain: J. Am. Chem. Soc., 105, 5706 (1983); Science, 222, 39 (1983).
• In the presence of a Lewis acid e.g. TiCl₄ or TMS-OTf, undergoes the Mukaiyama aldol reaction with aldehydes to give methyl ɑɑ-dimethyl-?-hydroxy esters: Chem. Lett., 989 (1975); Synth. Commun., 13, 449 (1983). Excellent results are obtained in these reactions with lanthanide triflates, e.g. Yb(OTf)₃, as catalysts: Synthesis, 371 (1993).
• With imines, gives ?-amino esters or ?-lactams according to conditions: Tetrahedron Lett., 3643 (1977); Chem. Lett., 1397 (1989); Tetrahedron, 44, 4157 (1988).
• Michael additions to enones, catalyzed by Yb(OTf)₃, have also been reported: Tetrahedron Lett., 33, 6815 (1992).