1,2-dibenzoyl-4,5-dimethyl-benzene | 52044-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-dibenzoyl-4,5-dimethyl-benzene
• 英文别名: 1,2-Dibenzoyl-4,5-dimethyl-benzol；1,2-Dimethyl-4,5-dibenzoyl-benzol；(2-Benzoyl-4,5-dimethylphenyl)-phenylmethanone
• CAS: 52044-75-4
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: JANMRUXYZBLSNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-dibenzoyl-4,5-dimethyl-benzene 在 钾硼氢 作用下， 以 甲醇 为溶剂， 以86%的产率得到5,6-二甲基-1,3-二苯基-2-苯并呋喃
  参考文献：
  名称：

  蒽核心的新途径：合成两个由1,3-二苯基异苯并呋喃和9,10-二苯基蒽衍生的水溶性单线态氧陷阱

  摘要：

  制备了两个水溶性1 O 2捕集阱：1,3-二苯基异苯并呋喃-5-钾-5,6-二羧酸☐酯和9,10-二苯基蒽-2,3,6,7-四羧酸☐酯的高产率制备了一种新的描述了对蒽骨架的访问。该合成的关键步骤包括1，3-二苯基异苯并呋喃与二甲基7-氧杂双环[2.2.1] -5-庚烯-2，3-二甲叉基羧酸酯之间的环加成；这样得到的加合物经过脱水得到相应的蒽。

  DOI：

  10.1016/0040-4020(82)80224-x
• 作为产物：
  描述：

  (4,5-二甲基-4-环己烯-1,2-二基)二[苯基-甲酮 在 磷酸 、 溴 、 sodium acetate 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 生成 1,2-dibenzoyl-4,5-dimethyl-benzene
  参考文献：
  名称：

  Photophysical, Electrochemical, and Electrogenerated Chemiluminescent Properties of 9,10-Dimethyl-7,12-diphenylbenzo[k]fluoranthene and 9,10-Dimethylsulfone-7,12-diphenylbenzo[k]fluoranthene

  摘要：

  A newly synthesized light emitting compound 9,10-dimethylsulfone-7,12-diphenylbenzo[k]fluoranthene (DSDPBF) and its synthetic intermediate 9, 10-dimethyl-7,12-diphenylbenzo[k] fluoranthene (DMDPBF) were studied to evaluate how the addition of weak electron donating methyl groups and the subsequent addition of an electron withdrawing sulfone group affect the photophysical and electrochemical properties as well as the rate of radical cation coupling of the parent compound, 7,12-diphenylbenzo[k]fluoranthene (DPBF). Although the photochemical and electrochemical properties of DSDPBF were more similar to the unsubstituted DPBF than to the DMDPBF, there was a substantial decrease in the quantum efficiency upon addition of the electron-rich sulfone group which was not observed upon addition of the methyl groups. On the other hand, the rate of radical cation coupling or dimerization observed upon electrochemical oxidation varied significantly. The addition of the electron donating methyl groups decreased the reactivity of the radical cation resulting in a 40 times slower rate of dimerization than that observed for the unsubstituted benzo[k]fluoranthene, whereas the addition of the electron withdrawing sulfone group to the methyl groups increased the radical cation reactivity resulting in a rate of dimerization that was 3 times faster than the unsubstituted parent compound. As a result, the electrogenerated chemiluininescence emission spectrum obtained from the annihilation reaction between the radical anion and radical cations of DSDPBF was dominated by emission from the dimer at 589 and 621 nm instead of emission from the monomer at ca. 485 nm.

  DOI：

  10.1021/jp012012s

文献信息

• Skeletal Transformation of Unactivated Arenes Enabled by a Low-Temperature Dearomative (3 + 2) Cycloaddition
  作者：Sajan Pradhan、Fahimeh Mohammadi、Jean Bouffard

  DOI：10.1021/jacs.3c02314

  日期：2023.6.7

  exchange of the ring carbons: a two-carbon fragment from the original aromatic ring is replaced with another from the incoming dienophile, introducing an unconventional disconnection for the synthesis of ubiquitous aromatic building blocks. Applications of this two-step sequence to the preparation of substituted acenes, isotopically labeled molecules, and medicinally relevant compounds are demonstrated

  像苯这样的简单芳香族化合物是丰富的原料，其衍生物的制备主要从亲电取代反应开始，或者较少见的是还原反应。它们的高稳定性使它们特别不愿意在普通反应条件下参与环加成反应。在这里，我们展示了 1,3-diaza-2-azoniaallene 阳离子在室温下与未活化的苯衍生物进行形式 (3 + 2) 环加成的特殊能力，提供了多克级的热稳定脱芳构化加合物。容忍极性官能团的环加成激活环以进一步细化。在用亲二烯体处理时，环加合物会经历 (4 + 2) 环加成-环逆转级联反应，产生取代或稠合的芳烃，包括萘衍生物。整个序列通过环碳的交换导致芳烃的转化：来自原始芳环的双碳片段被来自进入的亲双烯体的另一个取代，为普遍存在的芳香结构单元的合成引入非常规的断开。证明了该两步序列在制备取代并苯、同位素标记分子和医学相关化合物中的应用。
• The Synthesis of 1,3-Diphenyldihydroisobenzofurans, 1,3-Diphenylisobenzofurans and o-Dibenzoylbenzenes from the Diene Addition Products to Dibenzoylethylene
  作者：Roger Adams、Marvin H. Gold

  DOI：10.1021/ja01858a012

  日期：1940.1
• Ried,W.; Boennighausen,K.H., Justus Liebigs Annalen der Chemie, 1961, vol. 639, p. 61 - 67
  作者：Ried,W.、Boennighausen,K.H.

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• Synthesis of 9-Arylanthracenes
  作者：J. B. Miller

  DOI：10.1021/jo01350a047

  日期：1966.12
• Synthesis of Polycyclic Quinones Including Some Furo- and Thieno-Fused Polycyclic Quinones
  作者：L. Lepage、Y. Lepage

  DOI：10.1055/s-1982-29989

  日期：——