10-羟基-10-苯基蒽-9-酮 | 5146-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 10-羟基-10-苯基蒽-9-酮
• 英文名称: 10-phenyl-10-hydroxy-9-anthracenone
• 英文别名: 10-Hydroxy-10-phenyl-anthron；9-Hydroxy-9-phenyl-anthron；10-Hydroxy-10-phenyl-9-anthron；9-hydroxy-9-phenylanthrone；10-Hydroxy-10-phenyl-anthron-(9)；10-Hydroxy-10-phenyl-9(10H)-anthracenone；10-hydroxy-10-phenylanthracen-9-one
• CAS: 5146-30-5
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: GPYIJEJINDRVKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  10-羟基-10-苯基蒽-9-酮 在 苯 作用下， 生成 10-acetoxy-10-phenyl-anthrone
  参考文献：
  名称：

  Hydroxy- and Methoxyphenylanthrones. III¹

  摘要：

  DOI：

  10.1021/ja01868a084
• 作为产物：
  描述：

  2-(diphenylmethyl)benzoic acid 在 sodium dichromate 、 溶剂黄146 、 zinc(II) chloride 作用下， 生成 10-羟基-10-苯基蒽-9-酮
  参考文献：
  名称：

  Hydroxy- and Methoxyphenylanthrones. III¹

  摘要：

  DOI：

  10.1021/ja01868a084

文献信息

• Reactions of cupric halides with organic compounds—VII
  作者：A.D. Mosnaim、D.C. Nonhebel、J.A. Russell

  DOI：10.1016/s0040-4020(01)98790-3

  日期：1970.1

  9-Alkoxy(or acyloxy)-10-methylanthracenes undergo reaction with cupric halides at the Me group to give coupled products, whereas 9-alkoxy(or acyloxy)-10-benzyl(or ethyl)anthracenes react at the alkoxy or acyloxy group to afford 10-benzyl- and 10-ethylideneanthrones respectively. Both types of reaction are postulated to proceed by a radical mechanism.

  9-烷氧基（或酰氧基）-10-甲基蒽与Me基卤化铜反应生成偶联产物，而9-烷氧基（或酰氧基）-10-苄基（或乙基）蒽在烷氧基或酰氧基反应生成分别得到10-苄基和10-亚乙基蒽酮。两种反应都假定是通过自由基机理进行的。
• Reactions of copper(II) halides with aromatic compounds—XI
  作者：J.M. Mancilla、D.C. Nonhebel、J.A. Russell

  DOI：10.1016/0040-4020(75)80155-4

  日期：1975.1

  9-Alkyl and 9-arylanthracenes react with copper(II) bromide in methanol to give 10-alkyl (or aryl)-10-methoxyanthrones as the major product. 9-Methylanthracene additionally affords 10-methoxy-10-methoxymethylanthrone. The formation of all these products can be interpreted in terms of an initial electron-transfer oxidation of the aromatic moiety to the radical cation.

  9-烷基和9-芳基蒽与甲醇中的溴化铜（II）反应生成主要产物10-烷基（或芳基）-10-甲氧基蒽。9-甲基蒽另外提供10-甲氧基-10-甲氧基甲基蒽。所有这些产物的形成可以根据芳族部分向自由基阳离子的初始电子转移氧化来解释。
• Substituent Effects on the Ionization Equilibria of 9-Aryl-9-fluorenols and 10-Aryl-10-hydroxyanthracen-9-ones
  作者：Trevor W. Toone、Edward Lee-Ruff、Alan C. Hopkinson

  DOI：10.1139/v75-230

  日期：1975.6.1

  The title compounds were prepared and their basicities measured. In both systems the major part of the molecule is held planar, while an aryl group is free to rotate. This may interact with the positive charge but steric hindrance to the ortho hydrogens may be expected to oppose planarity. In these systems no evidence was found for a reduction of the normal σ⁺ value due to failure to achieve planarity. A formula is presented which gives the approximate degree of resemblance (α) of the transition state to the products and, in the case of the ionization of triarylmethanols, α is found to be linear with pK_R+. It is suggested that this could resolve the apparent contradiction between the Hammett equation and the Hammond postulate.

  这些标题化合物已经制备并测量了它们的碱性。在这两个体系中，分子的主要部分保持平面，而芳基团可以自由旋转。这可能会与正电荷发生相互作用，但对邻位氢的立体位阻可能会阻碍平面性。在这些体系中，没有发现由于无法实现平面性而导致正常σ⁺值降低的证据。提出了一个公式，该公式给出了过渡态与产物之间近似相似度（α），在三芳基甲醇离子化的情况下，发现α与pK_R+呈线性关系。建议这可能解决汉密特方程与哈蒙德假设之间的明显矛盾。
• Photo-oxygénation d'amines aromatiques endoperoxydes d'amino-9 anthracènes
  作者：Jean Santamaria、Jean Rigaudy

  DOI：10.1016/0040-4020(80)80223-7

  日期：1980.1

  The direct photo-oxygenation of 10-phenyl and 10-methoxy-9-dimethylaminoanthracenes 1a and 1b gives the corresponding 9,10-endoperoxides 2a and 2b. The latter are unstable owing to their high reactivity towards nucleophiles.

  10-苯基和10-甲氧基-9-二甲基氨基蒽1a和1b的直接光氧合得到相应的9,10-内过氧化物2a和2b。后者由于对亲核试剂的高反应性而不稳定。
• The oxidation of organic compounds by “singlet” oxygen
  作者：E. McKeown、William A. Waters

  DOI：10.1039/j29660001040

  日期：——

  The normal or “triplet” ground state (3Σg–) of molecular oxygen is that of a biradical, ·O–O·, but “singlet” oxygen (1Δg) OO, which is structurally similar to ethylene, is the initial product of heterolytic decompositions of hydrogen peroxide or of per-acids. “Singlet” oxygen reverts to normal “triplet” oxygen by a bimolecular reaction that produces chemiluminescence but is sufficiently long-lived

  正常或“三联体”基态（3 Σ克- ）分子氧的是一个双自由基的，·O-O·，但“单峰”氧（1 Δ克）O O，其在结构上类似于乙烯，是过氧化氢或过酸的杂化分解的初始产物。“单重态”氧通过双分子反应恢复为正常的“三重态”氧，该化学反应产生化学发光，但寿命足够长，可以作为双烯亲体反应。它在其内消旋位置与蒽环碳氢化合物结合，或添加到合适的1,3-二烯中。

表征谱图