2-bromo<1,1-2H2>ethanol | 40146-66-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2-bromo<1,1-2H2>ethanol
• 英文别名: 1-d2-2-Bromoethanol；2-bromo-1,1-dideuteriethanol；<1,1-2H2>-2-Bromethanol；1.1-d(2)-2-Bromethanol；2-bromo-1,1-dideuterio-ethanol；2-Bromo-1,1-dideuterioethanol
• CAS: 40146-66-5
• 化学式: C₂H₅BrO
• 分子量: 126.949
• InChiKey: LDLCZOVUSADOIV-CBTSVUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  4
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo<1,1-2H2>ethanol 、 鸟苷 生成 N-7-(2-d2-Hydroxyethyl)guanine
  参考文献：
  名称：

  Tandem mass spectrometric approaches for the analysis of alkylguanines in human urine

  摘要：

  AbstractHuman exposure to carcinogenic alkylating agents can lead to the formation of covalently bound adducts in DNA, some of which are excreted in urine as alkylated purines following DNA degradation and repair. Tandem mass spectrometric methods have been developed for the qualitative and quantitative determination of such alkylpurines in human urine. Short‐chain alkyl‐ and hydroxyalkylguanines have been synthesized with the substituents at theN‐7‐,O6‐ andN2‐positions of guanine. Examination of the product ion scans of their molecular ions (electron impact (EI) ionization) revealed that the ion atm/z151, [guanine]+, was common to all of the alkylguanines studied, with the exception of the methylated analogues. Precursor ion scans of this ion on partially purified human urine extracts showed the presence of several ions (e.g.m/z179, 195) which were consistent with molecular ions for alkylguanines. The presence of these and other constituents was confirmed by product ion spectra of molecular ions (EI and fast atom bombardment), and by high‐performance liquid chromatographic separation prior to tandem mass spectrometry (MS/MS). Evidence was obtained for the presence ofN‐7‐methyl‐,N2‐dimethyl‐,N2‐dimethyl‐,N2‐ethyl‐ andN‐7‐(2‐hydroxyethyl)guanine. Quantitative methods were established for these five alkyl guanines using gas chromatography mass spectrometry (GC/MS) and GC/MS/MS. Deuterated internal standards were synthesized and added to the urine prior to extraction of alkylpurines by Sep‐Pak cartridge chromatography. The products were converted into theirtert‐butyldimethylsilyl derivatives and analysed by selected ion monitoring (SIM) of [M – 57]+or by multiple reaction monitoring (MRM) of the fragmentation M+˙→ [M – 57]+. The MRM method yielded values forN‐7‐methylguanine of 2.57 ± S.D. 1.32 mg day−1(n= 6),N2‐methylguanine of 0.31 ± 0.10 mg day−1(n= 10) andN2‐dimethylguanine of 0.21 ± 0.23 mg day−1(n= 10).N2‐Ethyl‐ andN‐7‐(2‐hydroxyethyl)guanine could only be detected by SIM at levels of ∼0.5 and 2 μg day−1, respectively. The MRM analyses, although inherently less sensitive than the SIM analyses, exhibit greater selectivity and consequently fewer contaminant ions.

  DOI：

  10.1002/oms.1210280514
• 作为产物：
  描述：

  2-bromo<1,1-²H2>ethyl phenylmethyl ether 以69%的产率得到
  参考文献：
  名称：

  BIRD, IAN;FARMER, PETER B., J. LABELL. COMPOUNDS AND RADIOPHARM., 27,(1989) N, C. 199-216

  摘要：

  DOI：

文献信息

• Tetracyclo[5.2.0.01,6.02,7]nonane, A [2.1.1]propellane derivative as a reaction intermediate
  作者：Jan Morf、Günter Szeimies

  DOI：10.1016/s0040-4039(00)85211-9

  日期：1986.1
• Synthesis of (R)- and (S)-1-amino[2,2-2H2]cyclopropane-1-carboxylic acids
  作者：Pullachipatti K. Subramanian、Ronald W. Woodard

  DOI：10.1021/jo00377a003

  日期：1987.1
• BIRD, IAN;FARMER, PETER B., J. LABELL. COMPOUNDS AND RADIOPHARM., 27,(1989) N, C. 199-216
  作者：BIRD, IAN、FARMER, PETER B.

  DOI：——

  日期：——
• BRUNDRETT R. B., J. MED. CHEM., 1980, 23, NO 11, 1245-1247
  作者：BRUNDRETT R. B.

  DOI：——

  日期：——
• RAMALINGAM, KONDAREDDIAR;KALVIN, D.;WOODARD, R. W., J. LABELLED COMPOUNDS AND RADIOPHARM., 1984, 21, N 9, 833-841
  作者：RAMALINGAM, KONDAREDDIAR、KALVIN, D.、WOODARD, R. W.

  DOI：——

  日期：——