tributyl(prop-2-en-1-yl)stannane

• ChemBase编号: 65051
• 分子式: C15H32Sn
• 平均质量: 331.11558
• 单一同位素质量: 332.15259502
• SMILES: C=CC[Sn](CCCC)(CCCC)CCCC
• Canonical SMILES: C=CC[Sn](CCCC)(CCCC)CCCC
• InChI: InChI=1S/3C4H9.C3H5.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;3H,1-2H2
• InChIKey: YLGRTLMDMVAFNI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: tributyl(prop-2-en-1-yl)stannane
• IUPAC传统名: tributyl(prop-2-en-1-yl)stannane
• 别名: 烯丙基三丁基锡; 丙烯基三丁基锡; Allyltributylstannane; Allyltri-n-butyltin; Allyltributyltin; Tributyl-2-propenylstannane; Allyltributylstannane; Allyltri-n-butylstannane; Tri-n-butyl-2-propenylstannane; Allyltri-n-butyltin; Allyltributylstannane; Allyltributyltin

登记号

• CAS号: 24850-33-7
• EC号: 246-494-3
• MDL号: MFCD00010346
• Beilstein号: 3588340
• PubChem SID: 162030790; 24856436
• PubChem CID: 90628

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 7.4548
• LogD (pH = 7.4): 7.4548
• Log P: 7.4548
• 摩尔折射率: 73.1767 cm^3
• 极化性: 33.411934 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

分子性质

理化性质

• 沸点: 100-102°C/0.5mm; 88-92 °C/0.2 mmHg(lit.); 88-92°C/0.2mm
• 闪点: >110°C; 103 °C; 103°C(217°F); 217.4 °F
• 密度: 1.068; 1.068 g/mL at 25 °C(lit.); 1.079
• 折射率: 1.4860; n20/D 1.486; n20/D 1.486(lit.)

安全信息

• 保存注意事项: Air Sensitive; IRRITANT; Toxic
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有毒(Toxic) (T)
• 联合国危险货物编号: 2788; UN2788
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 21-25-36/38-48/23/25-50/53
• 安全公开号: 35-36/37/39-45-60-61; 36/37/39-45-60-61
• TSCA收录: false; 否
• GHS危险品标识: GHS06; GHS08; GHS09
• GHS警示词: Danger
• GHS危险声明: H301-H312-H315-H319-H372-H400-H410; H301-H312-H315-H319-H372-H410
• GHS警示性声明: P260-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P273-P280-P301 + P310-P305 + P351 + P338-P314-P501
• 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 2788 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0% (GC); 97%
• 级别: purum
• 线性分子式: CH2=CHCH2Sn(CH2CH2CH2CH3)3

详细说明

Sigma Aldrich - 271411

包装
5, 25, 100 g in glass bottle
Application
醛的烯丙基化试剂，该反应的催化剂为手性路易斯酸1,2和三氟甲烷磺酸镱(III)（产品号430595）。3在四(三苯基膦)钯(0)（产品号216666）催化下，与碘醌4和乙酸烯丙酯发生偶联反应。5,6 7用于醛与三氯-1,3,5-三氮烯的高效烯丙基化反应，生成高烯丙醇。

Sigma Aldrich - 06068

Other Notes
烯丙基化反应的试剂1,2,3

参考文献

• Widely used nucleophilic, non-basic allylating agent.
• Couples with primary or secondary alkyl halides under free-radical conditions: J. Am. Chem. Soc., 104, 5829 (1982); Bull. Chem. Soc. Jpn., 56, 24801 (1983).
• Lewis acid-catalyzed stereoselective addition to aldehydes gives homoallylic alcohols: Chem. Lett., 919 (1979); Tetrahedron Lett., 25, 265, 1879 (1984); Synlett, 1694 (2002). For chemoselective allylation of aldehydes in the presence of ketones, see: Tetrahedron Lett., 36, 3723 (1995). In the presence of TI(O-i-Pr)₄ and BINOL, enantioselective allylation of ketones can be accomplished with high ee: Tetrahedron: Asym., 11, 4163 (2000).
• Similarly, homoallylamines are formed from aldimines with TiCl₄ or BF₃ etherate: J. Org. Chem., 50, 146 (1985). For allylation of quinones, see p-Benzoquinone, A13162.