anti-2,3-dihydroxy-1,10b-epoxy-1,2,3,10b-tetrahydrofluoranthene | 83349-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: anti-2,3-dihydroxy-1,10b-epoxy-1,2,3,10b-tetrahydrofluoranthene
• 英文别名: (1R,3S,4S,5R)-2-oxapentacyclo[8.6.1.01,3.06,17.011,16]heptadeca-6,8,10(17),11,13,15-hexaene-4,5-diol
• CAS: 83349-67-1
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: XFISQOLBVZLENT-FXUDXRNXSA-N

物化性质

• 熔点：
  126-129 °C (decomp)
• 沸点：
  515.0±50.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  L-valine N-methylamide 、 anti-2,3-dihydroxy-1,10b-epoxy-1,2,3,10b-tetrahydrofluoranthene 以 水 、 叔丁醇 为溶剂， 反应 35.0h， 生成 N-(3R,2S,1R,10bS)-(1,2,3-trihydroxy-1,2,3,10b-tetrahydrofluoranthen-t-10b-yl)-L-valine methylamide 、 N-(3S,2R,1S,10bR)-(1,2,3-trihydroxy-1,2,3,10b-tetrahydrofluoranthen-t-10b-yl)-L-valine methylamide
  参考文献：
  名称：

  Synthesis and Characterisation of N-Alkylated L-Valine Methylamide Products from Diol Epoxide Metabolites of Fluoranthene and Benzo[a]pyrene.

  摘要：

  The reactive diol epoxides of fluoranthene and benzo[a]pyrene, (+/-)-anti-c-I,c-10b-epoxy-1,2,3,10b-tetrahydrofluoranthene-r-2,t-3-diol (1) and (+/-)-anti-t-9,t-10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene-r-7,t-8-diol (4), respectively, are known genotoxic agents and effective alkylators of nucleophilic sites in DNA and proteins. As models of in vivo N-alkylation at the N-termini of hemoglobin (Hb), N-L-valine methylamide (VMA) products of 1 and 4 were synthesised, N-(r-1,c-2,t-3-trihydroxy-1,2,3.10b-tetrahydrofluoranthen-t-10b-yl)-L-valine methylamide (2a,b) and N-(r-7,t-8,t-9-trihydroxy-7,8,9,10-tetrahydrobenzo[a]pyren-c-10-yl)-L-valine methylamide (5a,b), respectively. For isolation of the reaction products from the alkylation of VMA two reversed-phase HPLC systems were developed. From each diol epoxide two diastereoisomeric products were isolated in separate fractions. The products were characterised by H-1 NMR spectroscopy as well as by thermospray (TSP) tandem quadrupole mass spectrometry (MS and MS/MS) and fluorescence. When analysed by TSP-MS/MS the quasimolecular ions, [M+H](+), have a neutral loss of either the VMA or the 1 and 4 adduct moieties, respectively. The major daughter ion from 5a,b is the adduct moiety and the corresponding ion from 2a,b is the VMA moiety. Minor daughter ions are, in both cases, [(M-VMA)H+](+) ions with additional loss of H2O or H2O+CO. The higher the number of hydroxy groups in the 2a,b ions, the more easily is the C10b-amino bond disrupted in collision-induced dissociation.

  DOI：

  10.3891/acta.chem.scand.52-0797
• 作为产物：
  描述：

  荧蒽-2,3-二酮 在 sodium tetrahydroborate 、 氧气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 51.0h， 生成 anti-2,3-dihydroxy-1,10b-epoxy-1,2,3,10b-tetrahydrofluoranthene
  参考文献：
  名称：

  A study of chemical carcinogenesis. 109. Oxidation of polynuclear aromatic hydrocarbons with ceric ammonium sulfate: preparation of quinones and lactones

  摘要：

  DOI：

  10.1021/jo00240a013

文献信息

• Fluoranthene: synthesis and mutagenicity of four diol epoxides
  作者：William H. Rastetter、Robert B. Nachbar、Sandra Russo-Rodriguez、Ruth V. Wattley、William G. Thilly、Barbara M. Andon、William L. Jorgensen、Mustafa Ibrahim

  DOI：10.1021/jo00146a011

  日期：1982.12
• RASTETTER, W. H.;NACHBAR, R. B. ,, JR;RUSSO-RODRIGUEZ, S.;WATTLEY, R. V.;+, J. ORG. CHEM., 1982, 47, N 25, 4873-4878
  作者：RASTETTER, W. H.、NACHBAR, R. B. ,, JR、RUSSO-RODRIGUEZ, S.、WATTLEY, R. V.、+

  DOI：——

  日期：——
• A study of chemical carcinogenesis. 109. Oxidation of polynuclear aromatic hydrocarbons with ceric ammonium sulfate: preparation of quinones and lactones
  作者：George Balanikas、Nalband Hussain、Shantu Amin、Stephen S. Hecht

  DOI：10.1021/jo00240a013

  日期：1988.3
• Synthesis and Characterisation of N-Alkylated L-Valine Methylamide Products from Diol Epoxide Metabolites of Fluoranthene and Benzo[a]pyrene.
  作者：Hans Helleberg、Roger Westerholm、Lars Ehrenberg、Margareta Törnqvist、Yngve Stenstrøm、Ruo-Hua Zhang、Kurt V. Mikkelsen、Alexander Senning

  DOI：10.3891/acta.chem.scand.52-0797

  日期：——

  The reactive diol epoxides of fluoranthene and benzo[a]pyrene, (+/-)-anti-c-I,c-10b-epoxy-1,2,3,10b-tetrahydrofluoranthene-r-2,t-3-diol (1) and (+/-)-anti-t-9,t-10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene-r-7,t-8-diol (4), respectively, are known genotoxic agents and effective alkylators of nucleophilic sites in DNA and proteins. As models of in vivo N-alkylation at the N-termini of hemoglobin (Hb), N-L-valine methylamide (VMA) products of 1 and 4 were synthesised, N-(r-1,c-2,t-3-trihydroxy-1,2,3.10b-tetrahydrofluoranthen-t-10b-yl)-L-valine methylamide (2a,b) and N-(r-7,t-8,t-9-trihydroxy-7,8,9,10-tetrahydrobenzo[a]pyren-c-10-yl)-L-valine methylamide (5a,b), respectively. For isolation of the reaction products from the alkylation of VMA two reversed-phase HPLC systems were developed. From each diol epoxide two diastereoisomeric products were isolated in separate fractions. The products were characterised by H-1 NMR spectroscopy as well as by thermospray (TSP) tandem quadrupole mass spectrometry (MS and MS/MS) and fluorescence. When analysed by TSP-MS/MS the quasimolecular ions, [M+H](+), have a neutral loss of either the VMA or the 1 and 4 adduct moieties, respectively. The major daughter ion from 5a,b is the adduct moiety and the corresponding ion from 2a,b is the VMA moiety. Minor daughter ions are, in both cases, [(M-VMA)H+](+) ions with additional loss of H2O or H2O+CO. The higher the number of hydroxy groups in the 2a,b ions, the more easily is the C10b-amino bond disrupted in collision-induced dissociation.