cis-5,6-dihydroxy-5,6-dihydrobenzanthracene | 3719-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: cis-5,6-dihydroxy-5,6-dihydrobenzanthracene
• 英文别名: (+/-)-benzanthracene trans-5,6-dihydrodiol；cis-5,6-dihydroxy-5,6-dihydrobenz[a]anthracene；trans-5,6-Dihydrobenz(a)anthracene-5,6-diol；(5S,6S)-5,6-dihydrobenzo[c]anthracene-5,6-diol
• CAS: 3719-37-7
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: DCXCOTLBZGXMOH-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

SDS

反应信息

• 作为产物：
  描述：

  benzo[a]anthracene-5,6-dione 在 钾硼氢 作用下， 以 异丙醇 为溶剂， 生成 cis-5,6-dihydroxy-5,6-dihydrobenzanthracene
  参考文献：
  名称：

  Resolution and absolute configuration of K-region trans dihydrodiols from polycyclic aromatic hydrocarbons

  摘要：

  DOI：

  10.1021/jo00360a024

文献信息

• Solvolysis of K-region arene oxides: substituent effects on reactions of benz[a]anthracene 5,6-oxide
  作者：Nashaat T. Nashed、Suresh K. Balani、Richard J. Loncharich、Jane M. Sayer、David Y. Shipley、Ram S. Mohan、Dale L. Whalen、Donald M. Jerina

  DOI：10.1021/ja00010a036

  日期：1991.5

  dioxane-water and in methanol at 25 o C are reported. These substitutions result in >150-fold differences in their rates of acid-catalyzed solvolysis and cause marked changes in the distribution of solvent adducts and phenols resulting from isomerization. Optically pure BA-O, 7-MBA-O, 12-MBA-O, and 7,12-DMBA-O as well as their optically pure trans dihydrodiols were utilized to determine the point of attack by

  苯并 [a] 蒽 5,6-氧化物 (BA-O) 在取代 1 (1-MBA-O)、4 (4-MBA-O)、7 ( 7-MBA-O)、11 (11-MBA-O) 和 12 (12-MBA-O)、7,12-二甲基取代 (7,12-DMBA-O) 和 7-溴取代1:9 二恶烷-水和甲醇在 25 o C 报告。这些取代导致其酸催化溶剂分解的速率差异 > 150 倍，并导致异构化导致的溶剂加合物和酚类的分布发生显着变化。利用光学纯的 BA-O、7-MBA-O、12-MBA-O 和 7,12-DMBA-O 以及它们的光学纯反式二氢二醇来确定水解反应中水的攻击点
• K-Region<i>trans</i>-Dihydrodiols of Polycyclic Arenes; An Efficient and Convenient Preparation from<i>o</i>-Quinones or<i>o</i>-Diphenols by Reduction with Sodium Borohydride in the Presence of Oxygen
  作者：Karl L. Platt、Franz Oesch

  DOI：10.1055/s-1982-29834

  日期：——
• Photoemission probes of hydrocarbon-DNA interactions: a comparison of DNA influences on the reactivities of (.+-.)-trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene, benzo[a]pyrene 4,5-oxide, and benz[a]anthracene 5,6-oxide
  作者：Shigeyuki Urano、Harry L. Price、Sharon M. Fetzer、Anita V. Briedis、Ann Milliman、Pierre R. LeBreton

  DOI：10.1021/ja00010a033

  日期：1991.5

  Time-resolved fluorescence and UV photoelectron measurements have been employed to examine the influence of calf thymus DNA on the reactivities of epoxides derived from benzo[a]pyrene (BP) and benz[a]anthracene (BA). By monitoring the increase in fluorescence intensity, which accompanies reaction at 23-degrees-C, overall, pseudo-first-order rate constants have been measured for reactions of the highly carcinogenic bay region epoxide (+/-)-trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (BPDE) and of two less carcinogenic K region epoxides benzo[a]pyrene 4,5-oxide (BPO) and benz[a]anthracene 5,6-oxide (BAO). Overall rate constants for hydrolysis and rearrangement reactions have been measured for BPDE, BPO, and BAO in buffer alone (1.0 mM sodium cacodylate, pH 7.1). The rate constants increase in the order BPO ((3.8 +/- 0.1) x 10(-6) s-1) < BAO ((5.7 +/- 2.6) x 10(-5) s-1) < BPDE ((7.2 +/- 1.0) x 10(-4) s-1). These results have been compared with overall rate constants for reactions, carried out in calf thymus DNA, which result in catalyzed hydrolysis and rearrangement, as well as DNA adduct formation. In DNA, the ordering of the rate constants for BPO and BAO changes from that observed in buffer alone. The rate constants increase in the order BAO ((2.8 +/- 0.1) x 10(-3) s-1) < BPO ((1.2 +/- 0.2) x 10(-2) s-1) < BPDE (approximately 1 x 10(-1) s-1). This ordering is the same as the ordering of association constants for the reversible binding to DNA of the fluorescent diols trans-7,8-dihydroxy-7,8-dihydro-BP (BP78D), trans-4,5-dihydroxy-4,5-dihydro-BP (BP45D) and cis-5,6-dihydroxy-5,6-dihydro-BA (BAD), which are model compounds of BPDE, BPO, and BAO, respectively. For the model compounds, the association constants for intercalation increase in the order BAD ((3.6 +/- 0.9( x 10(2) M-1) < BP45D ((9.6 +/- 0.5) x 10(3) M-1) < BP78D ((3.4 +/- 0.1) x 10(4) M-1). This ordering is consistent with the ordering of the association constants of BPDE ((2.5 +/- 0.3) x 10(4) M-1) and of BPO ((6.0 +/- 1.0) x 10(3) M-1). The temperature dependence of the association constants of the model compounds demonstrates that, for the intercalation of the BP diols into DNA, differences in the enthalpy of binding contribute significantly to differences in the free energy of binding. UV photoelectron data and results from ab initio molecular orbital calculations on BPDE, BPO, and BAO indicate that, for these three epoxides, the association constants increase as the ionization potentials decrease and the polarizabilities increase. The percentage of epoxide reaction that yields DNA adducts has been compared under varying conditions. For long reaction times (> 1 h) in systems containing native, calf thymus DNA at low salt concentrations, the ordering of adduct yields is BPO (14.9 +/- 1.1%) > BPDE (10.1 +/- 3.0%) > BAO (3.6 +/- 0.4%). For short reaction times (10 min) in systems containing native DNA stabilized with 0.10 mM Mg2+, the ordering of adduct yields is BPDE (7.3 +/- 1.9%) > BPO (1.3 +/- 0.1%) > BAO (0.1 +/- 0.1%). These results suggest that the ability of an epoxide to form adducts with exposed DNA during long reaction times is less indicative of the genotoxic potency of the epoxide than its ability to form adducts with stabilized DNA during short reaction times.
• BALANI S. K.; VAN BLADEREN P. J.; SHIRAI N.; JERINA D. M., J. ORG. CHEM., 51,(1986) N 10, 1773-1778
  作者：BALANI S. K.、 VAN BLADEREN P. J.、 SHIRAI N.、 JERINA D. M.

  DOI：——

  日期：——