问题：L-tyrosine（CAS No.60-18-4）的化学合成方法（10分）
类型：求助 (悬赏分:3分)
提问：netpanda
等级：▲▲▲
版块：有机合成(netpanda,yjgzfl,penance,)
信誉：80%
回复：9
阅读：1893
时间：2004-12-02 18:58:07 编辑加入/取消收藏订制/取消短消息举报该贴

朋友要做这东西，而且其客户指定要化学合成的。我由于时间比较的匆忙，所以在CA上随便翻了一下，但是基本都是生物提取或者生物合成的。哪位高手有时间的话，帮忙查找一下。谢谢了~！

回复人：pharmacy,▲ (药物化学) 时间：2004-12-02 19:03:55 编辑	1楼
如果好做，外国人都做过拉化学方法肯定不好做

回复人：netpanda,▲▲▲ (CHEM-IS-TRY!永远的求知者) 时间：2004-12-02 19:18:39 编辑	2楼
国外有人做，如Aldrich、Sigma、Fluck等都有的。就是价格问题吧。

回复人：penance,▲▲▲▲▲ (人生得意须尽欢) 时间：2004-12-02 19:21:06 编辑

3楼

Aldrich Library of FT-IR Spectra, 1st edn. , 1985, 2 , 255B; 255C; 255D; 258C; 268A; 270C; 284C; 383C, (ir) Aldrich Library of 13C and 1H FT NMR Spectra , 1992, 2 , 1187C; 1188A; 1188B; 1228A; 1228B; 1415A, (nmr) Sadtler Standard C-13 NMR Spectra , 12328, (cmr) Sadtler Standard Proton NMR Spectra , 27604, (pmr) Fischer, E. , Ber. , 1899, 32 , 3638; 1901, 34 , 433, (resoln, Et ester) Curtius, T. et al. , J. Prakt. Chem. , 1917, 95 , 349, (hydrazides, amide) Hodgden, H.W. et al. , Anal. Chem. , 1954, 26 , 1224, (detn, ClO 2 ) Greenstein, J.P. et al. , Chemistry of the Amino Acids , Wiley, N.Y., 1961, 3 , (rev) Parasarathy, R. , Acta Cryst. , 1962, 15 , 41, (cryst struct) Hooker, T.M. et al. , J.A.C.S. , 1964, 86 , 4989, (ord) Voellmin, J. et al. , Microchem. J. , 1966, 11 , 73, (ms) Tumanova, T.A. et al. , Zavod. Lab. , 1970, 36 , 1036, (detn, ClO 2 ) Mostad, A. et al. , Acta Chem. Scand. , 1971, 25 , 1145; 1972, 26 , 3819; 1973, 27 , 401, (cryst struct) Fries, D.C. et al. , Acta Cryst. B , 1971, 27 , 401-410, (cryst struct, O-sulfate) Pieret, A.F. et al. , Cryst. Struct. Commun. , 1972, 1 , 75, (cryst struct, Et ester) Fieser and Fieser's Reagents for Organic Synthesis, Wiley , 1972, 3 , 330, (hydrazide) Yamashiro, D. et al. , J.A.C.S. , 1973, 95 , 1310-1315, (O-2,6-dichlorobenzyl, derivs) Larsen, P.O. et al. , Phytochemistry , 1973, 12 , 2243, (Tyrosinyl glucoside) Ger. Pat. , 1975, 2 503 992; CA , 83 , 193728p, (N,O-bis(benzyloxycarbonyl)) Michel, A.G. et al. , Acta Cryst. B , 1976, 32 , 1574-1576, (Ac nitroanilide, cryst struct) Kasai, T. et al. , Agric. Biol. Chem. , 1976, 40 , 2489, (isol, amide) Tamada, M. et al. , Planta Med. , 1978, 34 , 291, (Maokonine) Van Heerden, F.R. et al. , Phytochemistry , 1980, 19 , 2125, (N-Coumaroyltyrosine) Bernard, T. et al. , Phytochemistry , 1981, 20 , 2325, (N,N-Dimethyltyrosine) Lu, P.W. et al. , Insect Biochem. , 1982, 12 , 377, (Tyrosinyl glucoside) Ullmann's Encycl. Ind. Chem. , 1985, A2 , 57, (rev) Brueckner, C. et al. , Phytochemistry , 1986, 25 , 2236, (N-Jasmonyltyrosine) Lubman, D.M. et al. , Anal. Chem. , 1987, 59 , 2538, (uv) Shiraiwa, T. et al. , Bull. Chem. Soc. Jpn. , 1987, 60 , 1465, (resoln) Cerovski, J. et al. , Coll. Czech. Chem. Comm. , 1987, 52 , 1079-1086, (O-sulfate) Lewis, R.J. , Food Additives Handbook , Van Nostrand Reinhold International, New York, 1989, TOG300 Dymicky, M. , Org. Prep. Proced. Int. , 1989, 21 , 83, (esters, synth) Pearson, A.J. et al. , J.O.C. , 1991, 56 , 7092, (esters, N-Ac) Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press , 1993, 665 Hare, J.D. et al. , Naturwissenschaften , 1993, 80 , 92, (O-Caffeoyltyrosine) Fenaroli's Handbook of Flavor Ingredients , 3rd edn., (ed. Burdock, G.A.), CRC Press, 1995, 2 , 778 Encyclopedia of Food and Color Additives , (ed. Burdock, G.A.), CRC Press, 1997, 2862-2863 Sanbongi, C. et al. , J. Agric. Food Chem. , 1998, 46 , 454-457, (4-hydroxycinnamoyl) Lewis, R.J. , Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold , 1992, TOG300

回复人：penance,▲▲▲▲▲ (人生得意须尽欢) 时间：2004-12-02 19:45:40 编辑	4楼
最好还是查CA吧我查了，但是没办法传给你怎么处理？

回复人：netpanda,▲▲▲ (CHEM-IS-TRY!永远的求知者) 时间：2004-12-03 20:40:38 编辑	5楼
谢谢几位,要是你觉得比较的符合的话,给我发E-mail给我吧:netpanda@126.com.谢谢了!

回复人：qixie,★ () 时间：2004-12-12 10:31:08 编辑

6楼

Non-essential amino acid for human development; precursor for the synthesis of thyroid hormones and select neurotransmitters, such as dopamine and norepinephrine. May be considered essential by the brain. Name derived from the Greek "tyros" for "cheese" from which it was first identified and isolated: J. Liebig, Ann. 57, 127 (1846); idem, ibid. 62, 257 (1847). Early chemistry and biochemistry: Amino Acids and Proteins, D. M. Greenberg, Ed. (Charles C. Thomas, Springfield, IL, 1951) 950 pp., passim; J. P. Greenstein, M. Winitz, Chemistry of the Amino Acids vol 1-3 (John Wiley and Sons, Inc., New York, 1961) pp. 2348-2367, passim. Synthesis of labeled form: Y. Watanabe et al., Acta Radiol. 376 (Suppl.), 110 (1991). Intrinsic fluorophore in proteins; used in characterizing structure and conformational changes: V. Giancotti et al., Biochim. Biophys. Acta 624, 60 (1980); S. T. Ferreira et al., Biophys. J. 66, 1185 (1994); B. Kierdaszuk et al., Photochem. Photobiol. 61, 319 (1995). Review of determn in blood: E. Robins, Meth. Biochem. Anal. 17, 287-309 (1969). Review of neurotransmitter synthesis: C. J. Gibson, Retina 2, 332-340 (1982). Review of toxicity: C. Laberge et al., Adv. Exp. Med. Biol. 206, 209-221 (1986). Review of post-translational phosphorylation: S. Atherton-Fessler et al., Semin. Cell Biol. 4, 433-442 (1993); sulfation: C. Niehrs et al., Chemico-Biolog. Interact. 92, 257-271 (1994).
这是merk上说的文献，你找出来，应该用帮助！

回复人：yjgzfl,★ (研究) 时间：2004-12-12 18:21:31 编辑	7楼
请netpanda接收答案以后尽快回复，以方便斑竹打分！

回复人：shecr,▲ (我思故我在) 时间：2004-12-13 15:21:29 编辑

8楼

Formula: C9H11NO3
Molecular Weight: 181.19
CAS Registry Number: 60-18-4
Chemical Structure:
This structure is also available as a 2d Mol file.
Other Names: L-Tyrosine; Tyrosine, L-; α-Amino-β-(4-hydroxyphenyl)propionic acid; (-)-α-Amino-p-hydroxyhydrocinnamic acid; p-Tyrosine; Benzenepropanoic acid, α-amino-4-hydroxy-, (S)-; L-p-Tyrosine; L-Phenylalanine, 4-hydroxy-; Propanoic acid, 2-amino-3-(4-hydroxyphenyl)-, (S)-; L-Tryosine; L-2-Amino-3-p-hydroxyphenylpropanoic acid
Condensed phase thermochemistry data
Phase change data
Reaction thermochemistry data
IR Spectrum
Mass Spectrum
References
Notes / Error Report
Other Data Available:
Gas phase ion energetics data
UV/Visible Spectrum
Gas phase kinetics (on kinetics web site)
Switch to calorie-based units

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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass Spectrum, References, Notes / Error Report
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein
DH - E.S. Domalski and E.D. Hearing
Quantity Value Units Method Reference Comment
ΔfH°solid -685.6 ± 1.5 kJ/mol Ccb Huffman, Fox, et al., 1937 Author's hf298=-165.54 kcal/mol; ALS
Quantity Value Units Method Reference Comment
ΔcH°solid -4428.1 ± 1.5 kJ/mol Ccb Huffman, Fox, et al., 1937 Author's hf298=-165.54 kcal/mol; ALS
ΔcH°solid -4481.7 kJ/mol Ccb Emery and Benedict, 1911 ALS
Quantity Value Units Method Reference Comment
S°solid,1 bar 214.01 J/mol*K N/A Cole, Hutchens, et al., 1963 DH
S°solid,1 bar 221.8 J/mol*K N/A Huffman and Ellis, 1937 Extrapolation below 90 K. 64.56 J/mol*K.; DH

Constant pressure heat capacity of solid
Cp,solid (J/mol*K) Temperature (K) Reference Comment
216.44 298.15 Cole, Hutchens, et al., 1963 DH
214.30 294.6 Huffman and Ellis, 1937 T = 87 to 295 K. Value is unsmoothed experimental datum.; DH

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Phase change data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass Spectrum, References, Notes / Error Report
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: J.S. Chickos
Enthalpy of sublimation
ΔsubH (kJ/mol) Temperature (K) Method Reference
101. ± 8. 412. - 512. LE Gaffney, Pierce, et al., 1977

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Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass Spectrum, References, Notes / Error Report
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: J.E. Bartmess
Individual Reactions
C9H10NO3- + H+ =
Quantity Value Units Method Reference Comment
ΔrH° 1407. ± 13. kJ/mol G+TS O'Hair, Bowie, et al., 1992 gas phase
Quantity Value Units Method Reference Comment
ΔrG° 1379. ± 13. kJ/mol CIDC O'Hair, Bowie, et al., 1992 gas phase

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IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass Spectrum, References, Notes / Error Report
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Coblentz Society, Inc.
Spectrum
A digitized version of this spectrum is not currently available.
Additional Data
Download spectrum in JCAMP-DX format.

Owner COBLENTZ SOCIETY
Collection (C) 2003 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Source reference COBLENTZ NO. 2217
Date Not specified, most likely prior to 1970
Data processing (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.

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Condensed Phase Spectrum

Notice: This spectrum may be better viewed with a Java capable browser.

For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).

Download (or view) spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner COBLENTZ SOCIETY
Collection (C) 2003 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin CITRUS EXPERIMENT STATION, UNIVERSITY OF FLORIDA (G. EDWARDS)
Source reference COBLENTZ NO. 3614
Date Not specified, most likely prior to 1970
Name(s) tyrosine
State SOLID (1.5 mg / 100 mg KBr PELLET)
Data processing DIGITIZED BY NIST FROM HARD COPY
Resoulution 4
Sampling procedure TRANSMISSION

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.

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Mass Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes / Error Report
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spec Data Center, S.E. Stein, director
Spectrum

Notice: This spectrum may be better viewed with a Java capable browser.

For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data
View image of digitized spectrum (can be printed in landscape orientation).

Download (or view) spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2002 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-2550
Instrument IE (eV) 70
EPA MS number 228180

All mass spectra in this site (plus many more) are available from the 2002 NIST/EPA/NIH Mass Spectral Library. This libary is available with software for Windows or as ASCII data.

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References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass Spectrum, Notes / Error Report
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Huffman, Fox, et al., 1937
Huffman, H.M.; Fox, S.W.; Ellis, E.L., Thermal data. VII. The heats of combustion of seven amino acids, J. Am. Chem. Soc., 1937, 59, 2144-21. [all data]

Emery and Benedict, 1911
Emery, A.G.; Benedict, F.G., The heat of combustion of compounds of physiological importance, Am. J. Physiol., 1911, 28, 301-307. [all data]

Cole, Hutchens, et al., 1963
Cole, A.G.; Hutchens, J.O.; Stout, J.W., Heat capacities from 11 to 305°K. and entropies of L-phenylalanine, L-proline, L-tryptophane, and L-tyrosine. Some free energies of formation, J. Phys. Chem., 1963, 67, 1852-1855. [all data]

Huffman and Ellis, 1937
Huffman, H.M.; Ellis, E.L., Thermal data. VIII. The heat capacities, entropies and free energies of some amino acids, J. Am. Chem. Soc., 1937, 59, 2150-2152. [all data]

Gaffney, Pierce, et al., 1977
Gaffney, J.S.; Pierce, R.C.; Friedman, L., J. Amer. Chem. Soc., 1977, 99, 4293. [all data]

O'Hair, Bowie, et al., 1992
O'Hair, R.J.; Bowie, J.H.; Gronert, S., Gas Phase Acidity of the alpha-Amino Acids, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 23. [all data]

回复人：netpanda,▲▲▲ (CHEM-IS-TRY!永远的求知者) 时间：2004-12-14 11:22:43 编辑	9楼
我知道shecr的数据是来自NIST的，对于合成没有太多的帮助。不过要谢谢你！我这段时间真的是很忙，没有时间来这．只好yjgzfl来好好的管理这个版块了．

得分人：penance-5,pharmacy-1,shecr-2,

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