527254
三甲基硅烷化重氮甲烷 溶液
2.0 M in diethyl ether
别名:
TMS-重氮甲烷溶液, (三甲硅烷)重氮甲烷
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关于此项目
线性分子式:
(CH3)3SiCHN2
化学文摘社编号:
分子量:
114.22
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1902903
InChI
1S/C4H10N2Si/c1-7(2,3)4-6-5/h4H,1-3H3
SMILES string
C[Si](C)(C)C=[N+]=[N-]
InChI key
ONDSBJMLAHVLMI-UHFFFAOYSA-N
concentration
2.0 M in diethyl ether
density
0.773 g/mL at 25 °C
storage temp.
2-8°C
General description
（三甲基硅烷基）重氮甲烷被认为是重氮甲烷的非爆炸性替代物，用于羰基衍生物（主要是酮）通过反应（如 Tiffeneau-Demjanov 重排）的同系化。
Application
反应物用于制备：
- 改善代谢稳定性和抗菌活性的天然产物大环内酯 (-)-A26771B 的大内酰胺类似物
- 白霉素 D 类似物作为蛋白激酶抑制剂用于肿瘤治疗
- 非天然 α-含 gem-二膦酸盐的氨基酸衍生物通过 Michael 加成反应
- 作为潜在透明质酸酶底物的封端 4-甲基伞形酮基透明质酸二糖和四糖
- Stictamides A-C 作为具有抗肿瘤侵袭活性的基质金属肽酶 12 (MMP12) 抑制剂
- 内皮素转换酶 (ECE) 抑制剂 WS 75624A 和 WS 75624B（通过交叉转移方法）
- 贝壳杉烯衍生物作为抗炎剂
- 毛叶假鹰爪素 C 类似物作为强效抗肿瘤药物通过激活纺锤体组装检查点发挥作用
- 咪唑并 [2,1-b] 苯并噻唑衍生物作为潜在的 p53 抑制剂
signalword
Danger
Hazard Classifications
Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Flam. Liq. 2 - STOT SE 1 Inhalation - STOT SE 3
target_organs
Central nervous system, Lungs
supp_hazards
存储类别
3 - Flammable liquids
wgk
WGK 3
flash_point_f
-31.0 °F - closed cup
flash_point_c
-35 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
法规信息
监管及禁止进口产品
此项目有
A new, stable, and safe reagent for the homologation of ketones.
Hashimoto N
Tetrahedron Letters, 21(48), 4619-4622 (1980)
Konrad Kowalewski et al.
Journal of chromatography. A, 1218(41), 7264-7274 (2011-09-13)
A novel three-step analytical method was developed which enables the simultaneous detection and identification of multifunctional oxygenated products resulting from the reaction of α-pinene with ozone. The method consists of the following steps: conversion of carbonyl groups to methyloximes using
Hélène Lebel et al.
The Journal of organic chemistry, 73(17), 6828-6830 (2008-07-30)
Rhodium- and copper-catalyzed methylenation reactions with trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol were used to react chemoselectively with aldehydes, alkoxymethylketones, and trifluoromethylketones in substrates also containing a less reactive carbonyl group. Terminal alkenes were obtained in high yields, and no protecting group
Homologation reaction of ketones with diazo compounds.
Candeias N R
Chemical Reviews, 116(5), 2937-2981 (2016)
Y Park et al.
Journal of agricultural and food chemistry, 49(3), 1158-1164 (2001-04-21)
Four different methods for methylating conjugated linoleic acid (CLA) were compared. The HCl/MeOH and BF(3)/MeOH methods were tested under different time and temperature combinations. Increasing temperature and/or incubation time for either method decreased the cis-9,trans-11 and trans-10,cis-12 isomers, but trans-9,trans-11/trans-10,trans-12
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