(2-Ethyl-5-oxo-hexyl) methylthiomethyl phthalate as by-product of the Swern oxidation:: Improved synthesis of ring-deuterated major metabolites of bis(2-ethylhexyl) phthalate

被引：10
作者：
Gilsing, HD [1 ]
Angerer, J
Prescher, D
机构：
[1] Inst Dunnschichttechnol & Mikrosensorik EV, D-14513 Teltow, Germany
[2] Univ Erlangen Nurnberg, Inst & Poliklin Arbeits Sozial & Umweltmed, D-91054 Erlangen, Germany
来源：
MONATSHEFTE FUR CHEMIE | 2003年 / 134卷 / 09期
关键词：
bis(2-ethylhexyl) phthalate; metabolites; isotopic labelling; oxidations; methylthiomethyl esters;
D O I：
10.1007/s00706-003-0044-y
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two ring-deuterated major metabolites of bis(2-ethylhexyl) phthalate were obtained in excellent yields by means of an improved oxidation procedure. The by-product of their interconversion by Swern oxidation is elucidated and a possible mechanism of its formation is proposed.
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收藏
页码：1207 / 1213
页数：7
相关论文
共 54 条
  • [1] APPLICATIONS OF ISOTOPE DIFFERENTIATION FOR METABOLIC STUDIES WITH DI-(2-ETHYLHEXYL) PHTHALATE
    ALBRO, PW
    HASS, JR
    PECK, CC
    JORDAN, ST
    CORBETT, JT
    SCHROEDER, J
    [J]. JOURNAL OF ENVIRONMENTAL SCIENCE AND HEALTH PART B-PESTICIDES FOOD CONTAMINANTS AND AGRICULTURAL WASTES, 1982, 17 (06) : 701 - 714
  • [2] Phthalate esters in children's toys - calls for product substitution
    Allen, B
    [J]. GREEN CHEMISTRY, 1999, 1 (04) : G102 - G104
  • [3] Quantitative detection of eight phthalate metabolites in human urine using HPLC-APCI-MS/MS
    Blount, BC
    Milgram, KE
    Silva, MJ
    Malek, NA
    Reidy, JA
    Needham, LL
    Brock, JW
    [J]. ANALYTICAL CHEMISTRY, 2000, 72 (17) : 4127 - 4134
  • [4] Levels of seven urinary phthalate metabolites in a human reference population
    Blount, BC
    Silva, MJ
    Caudill, SP
    Needham, LL
    Pirkle, JL
    Sampson, EJ
    Lucier, GW
    Jackson, RJ
    Brock, JW
    [J]. ENVIRONMENTAL HEALTH PERSPECTIVES, 2000, 108 (10) : 979 - 982
  • [5] Butte W, 2001, GEFAHRST REINHALT L, V61, P19
  • [6] CRONHOLM T, 1988, SYNTHESIS APPL ISOTO, P1
  • [7] METABOLITES OF THE PLASTICIZER DI(2-ETHYLHEXYL)PHTHALATE IN URINE SAMPLES OF WORKERS IN POLYVINYLCHLORIDE PROCESSING INDUSTRIES
    DIRVEN, HAAM
    VANDENBROEK, PHH
    ARENDS, AMM
    NORDKAMP, HH
    DELEPPER, AJGM
    HENDERSON, PT
    JONGENEELEN, FJ
    [J]. INTERNATIONAL ARCHIVES OF OCCUPATIONAL AND ENVIRONMENTAL HEALTH, 1993, 64 (08) : 549 - 554
  • [8] DOSSENA A, 1984, INT J PEPT PROT RES, V23, P198
  • [9] NEW SYSTEM FOR ACTIVATION OF DIMETHYL-SULFOXIDE IN PUMMERER-LIKE REACTIONS
    DOSSENA, A
    MARCHELLI, R
    CASNATI, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (08) : 370 - 371
  • [10] TERT-BUTYL BROMIDE-DIMETHYL SULFOXIDE REACTIONS - PUMMERER-LIKE REACTION WITH CARBOXYLIC-ACIDS AND N-PROTECTED AMINO-ACIDS
    DOSSENA, A
    MARCHELLI, R
    CASNATI, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (10): : 2737 - 2739
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