蒽1,2-氧化物 | 70411-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 蒽1,2-氧化物
• 中文别名: 细胞色素b565(9CI)
• 英文名称: 1,2-anthracene oxide
• 英文别名: Anthracene 1,2-oxide；1,2-epoxy-1,2-dihydro-anthracene；Anthracen-1,2-oxid；Anthra(1,2-b)oxirene, 1a,9b-dihydro-；1a,9b-dihydroanthra[1,2-b]oxirene
• CAS: 70411-24-4
• 化学式: C₁₄H₁₀O
• 分子量: 194.233
• InChiKey: YDFLROSXCLHLJV-UHFFFAOYSA-N

物化性质

• 熔点：
  130-134 °C (decomp)
• 沸点：
  377.0±21.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  蒽1,2-氧化物 生成 trans-1,2-Dihydroxy-1,2-dihydroanthracen
  参考文献：
  名称：

  AKHTAR M. N.; HAMILTON J. G.; BOYD D. R.; BRAUNSTEIN A.; SEIFRIED H. E.; +, J. CHEM. SOC. PERKIN TRANS. PART 1, 1979, NO 6, 1442-1446

  摘要：

  DOI：
• 作为产物：
  描述：

  [(1R,2R)-2,4-dibromo-1,2,3,4-tetrahydroanthracen-1-yl] acetate 、 sodium methylate 以33%的产率得到
  参考文献：
  名称：

  AKHTAR M. N.; HAMILTON J. G.; BOYD D. R.; BRAUNSTEIN A.; SEIFRIED H. E.; +, J. CHEM. SOC. PERKIN TRANS. PART 1, 1979, NO 6, 1442-1446

  摘要：

  DOI：

文献信息

• Synthesis and Solvolysis of Acridine 1,2- and 3,4-Oxides: Crystal Structure of Acridine 1,2-Oxide
  作者：Derek R. Boyd、R. Jeremy H. Davies、Lynne Hamilton、John J. McCullough、John F. Malone、H. Patricia Porter、Allison Smith、John M. Carl、Jane M. Sayer、Donald M. Jerina

  DOI：10.1021/jo00084a013

  日期：1994.3

  Acridine 1,2- and 3,4-oxides were synthesized from 3,4- and 1,2-dihydroacridine, respectively, via intermediate bromohydrin acetates. Crystals of acridine 1,2-oxide were sufficiently stable to allow the first determination of X-ray crystallographic structural features of a non-K-region arene oxide. Aqueous alkaline hydrolysis of the acridine 1,2- and 3,4-oxides produced trans-1,2-dihydrorxy-1,2-dihydroacridine and trans-3,4-dihydroxy-3,4-dihydroacridine, respectively. The former dihydrodiol was also obtained by a six-step synthesis from 3,4-dihydroacridine. Acid-catalyzed hydrolysis of acridine 1,2-oxide yielded the corresponding cis- and trans-1,2-dihydrodiols (20%) in addition to 1-hydroxy- (12%) and 2-hydroxyacridine (68%). By contrast, solvolysis of acridine 3,4-oxide under acid conditions gave 4-hydroxyacridine as the exclusive product. pH-rate profiles for hydrolysis of the acridine oxides in 1:9 dioxane-water at 25 degrees C were compared with those for anthracene 1,2-oxide, naphthalene 1,2-oxide, and quinoline 5,6- and 7,8-oxides. Second-order rate constants for the hydronium ion-catalyzed ring opening of anthracene 1,2-, acridine 3,4-, and acridine 1,2-oxide are 585, 7.81, and 0.45 M(-1) s(-2), respectively, and are 3-5 times larger than the rate constants for the corresponding naphthalene 1,2-, quinoline 7,8-, and quinoline 5,6-oxides. Rate constants for uncatalyzed ring opening of anthracene 1,2- and acridine 3,4-oxides (117 x 10(-5) s(-1) and 2.4 X 10(-5) s(-1), respectively) are about two to three times larger than the corresponding rate constants for naphthalene 1,2- and quinoline 7,8-oxides, whereas the rate of nucleophilic ring opening by hydroxide ion to give the trans-dihydrodiols is accelerated by less than a factor of 2 for the acridine oxides as compared with their quinoline analogs. The pH-rate profiles for solvolysis of the acridine oxides, like those of the quinoline oxides, exhibit a pH-independent region at pH values below the pK(a) of the ring nitrogen that is attributed to formation of an unreactive N-protonated species.
• Rao, S. Nagaraja; More O'Ferrall, Rory A.; Kelly, Sandra C., Journal of the American Chemical Society, 1993, vol. 115, # 13, p. 5458 - 5465
  作者：Rao, S. Nagaraja、More O'Ferrall, Rory A.、Kelly, Sandra C.、Boyd, Derek R.

  DOI：——

  日期：——
• Akhtar; Hamilton; Boyd, Journal of the Chemical Society. Perkin transactions I, 1979, vol. 6, p. 1442 - 1446
  作者：Akhtar、Hamilton、Boyd、Braunstein、Seifried、Jarina

  DOI：——

  日期：——
• AKHTAR M. N.; BOYD D. R.; HAMILTON J. G., J. CHEM. SOC. PERKIN TRANS., 1979, PART 1, NO 10, 2437-2440
  作者：AKHTAR M. N.、 BOYD D. R.、 HAMILTON J. G.

  DOI：——

  日期：——
• AKHTAR M. N.; HAMILTON J. G.; BOYD D. R.; BRAUNSTEIN A.; SEIFRIED H. E.; +, J. CHEM. SOC. PERKIN TRANS. PART 1, 1979, NO 6, 1442-1446
  作者：AKHTAR M. N.、 HAMILTON J. G.、 BOYD D. R.、 BRAUNSTEIN A.、 SEIFRIED H. E.、 +

  DOI：——

  日期：——