tert‐Butoxybis(dimethylamino)methane
作者： Willi Kantlehner , Albert Bowers
DOI: 10.1002/9780470842898.RB350.PUB2
关键词: Chemistry 、 Organic chemistry 、 Toluene 、 Acetonitrile 、 Reagent 、 Medicinal chemistry 、 Acetone 、 Diethyl ether 、 Aminal 、 Cyclohexane 、 Benzene
摘要: (1; R = tert-Bu) (tert-BAE) [5815-08-7] C9H22N2O (MW 174.33) InChI = 1S/C9H22N2O/c1-9(2,3)12-8(10(4)5)11(6)7/h8H,1-7H3 InChIKey = HXRAMSFGUAOAJR-UHFFFAOYSA-N (2; R = Me) (MAE) [1186-70-5] C6H16N2O (MW 132.24) InChI = 1S/C6H16N2O/c1-7(2)6(9-5)8(3)4/h6H,1-5H3 InChIKey = NCIMAYPZWJQYGN-UHFFFAOYSA-N (aminal esters reactive as aminomethylenating reagents (formylating reagents) for CH2- and NH2-acidic compounds. The tert-butyl analog is somewhat more than the methyl derivative; bis(dimethylamino)carbene can be generated from both compounds) Alternate Name: Bredereck's reagent. Physical Data: (1) bp 50–52 °C/12 mmHg; n20D = 1.4250. (2) 128 °C/760 32–33 °C/25 n20D = 1.4158. Solubility: miscible with nonpolar aprotic waterfree solvents (benzene, toluene, cyclohexane, diethyl ether, etc.); react protic like water (hydrolysis to DMF) or alcohols (alcoholysis affords DMF acetals). Even common acetonitrile acetone which are weakly CH-acidic aminal on heating. Form Supplied in: colorless weak yellow, strong amine-smelling liquids. Analysis of Reagent Purity: the best method 1H NMR spectroscopic examination a neat sample. Handling, Storage, Precautions: both compounds should handled in fume hood, strict exclusion atmospheric moisture. They stored tightly sealed containers refrigerator under an atmosphere dry nitrogen argon.
sci-hub.se 参考文章(104)
Willi Kantlehner, Synthesis of Iminium Salts, Orthoesters and Related Compounds Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Organic Synthesis. ,vol. 2, pp. 485- 599 ,(1991) , 10.1016/B978-0-08-052349-1.00166-9
Tsuneo Sato, Makoto Watanabe, Hiroshi Kobayashi, Ryoji Noyori, Stereocontrolled General Synthesis of Pyrimidine C-Nucleosides Having Branched-chain Sugar Moieties Bulletin of the Chemical Society of Japan. ,vol. 56, pp. 2680- 2699 ,(1983) , 10.1246/BCSJ.56.2680
Tsuneo Sato, Yoshihiro Hayakawa, Ryoji Noyori, A Stereocontrolled Total Synthesis of C-Nucleosides Bulletin of the Chemical Society of Japan. ,vol. 57, pp. 2515- 2525 ,(1984) , 10.1246/BCSJ.57.2515
R. Noyori, T. Sato, Y. Hayakawa, A stereocontrolled general synthesis of C-nucleosides Journal of the American Chemical Society. ,vol. 100, pp. 2561- 2563 ,(1978) , 10.1021/JA00476A057
Pauline Chabaud, Gérard Pèpe, Jérôme Courcambeck, Michel Camplo, Stereoselective synthesis of (3S, 4S)-tert-butyl-N-boc-3-ethyl-4-hydroxy-L-prolinate and (3S, 4R)-tert-butyl-N-boc-3-ethyl-4-hydroxy-L-prolinate Tetrahedron. ,vol. 61, pp. 3725- 3731 ,(2005) , 10.1016/J.TET.2005.02.006
Thomas A. Lessen, Donald M. Demko, Steven M. Weinreb, Synthesis of an advanced quinocarcin intermediate from 1-glutamic acid Tetrahedron Letters. ,vol. 31, pp. 2105- 2108 ,(1990) , 10.1016/0040-4039(90)80083-X
Daniel F. Lieberman, J. Donald Albright, A new and improved synthesis of 6-aryl-1,2,4-triazolo[4,3-b]pyridazines Journal of Heterocyclic Chemistry. ,vol. 25, pp. 827- 830 ,(1988) , 10.1002/JHET.5570250325
Xiao-Tao Chen, Clare E. Gutteridge, Samit K. Bhattacharya, Bishan Zhou, Thomas R. R. Pettus, Tony Hascall, Samuel J. Danishefsky, A CONVERGENT ROUTE FOR THE TOTAL SYNTHESIS OF THE ELEUTHESIDES Angewandte Chemie. ,vol. 37, pp. 185- 186 ,(1998) , 10.1002/(SICI)1521-3773(19980202)37:1/2<185::AID-ANIE185>3.0.CO;2-L
Kei Takeda, Shingo Yano, Masaaki Sato, Eiichi Yoshii, Synthesis of the upper spirotetronic acid fragment of kijanolide Journal of Organic Chemistry. ,vol. 52, pp. 4135- 4137 ,(1987) , 10.1021/JO00227A040
Raymond Conrow, Philip S. Portoghese, Efficient Preparation of Polyfunctional a-Diketones from Carboxylic Acids Journal of Organic Chemistry. ,vol. 51, pp. 938- 940 ,(1986) , 10.1021/JO00356A036