4,4-diphenyl-3,4-dihydronaphthalen-1(2H)-one | 72774-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4,4-diphenyl-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 4,4-diphenyl-1-tetralone；4,4-Diphenyl-1-tetralon；4,4-Diphenyl-2,3-dihydronaphthalen-1-one
• CAS: 72774-01-7
• 化学式: C₂₂H₁₈O
• 分子量: 298.384
• InChiKey: ZAEPPCWPYUUKJV-UHFFFAOYSA-N

物化性质

• 熔点：
  188-189 °C
• 沸点：
  441.0±45.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  alpha-酮戊二酸 、 苯 在 三氟甲磺酸 作用下， 以46%的产率得到4,4-diphenyl-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Electrophilic Chemistry of Biologically Important α-Ketoacids

  摘要：

  DOI：

  10.1021/jo9901945

文献信息

• Photoredox-Catalyzed Dimerization of Arylalkenes<i>via</i>an Oxidative [4+2] Cycloaddition Sequence: Synthesis of Naphthalene Derivatives
  作者：Donglei Wei、Yanru Li、Fushun Liang

  DOI：10.1002/adsc.201600587

  日期：2016.12.7

  We report a radical cation [4+2] annulation of arylalkenes to afford naphthalene derivatives using an organic photosensitizer (9‐mesityl‐10‐methylacridinium perchlorate) under visible light photocatalysis. In the presence of oxygen (in the air), the oxidative dimerization/intramolecular [4+2] cycloaddition of two alkene molecules provides 3,4‐dihydronaphthalen‐1(2H)‐ones in good to high yields. Under

  我们报道了在可见光光催化下，使用有机光敏剂（9-甲硅烷基-10-甲基ac啶高氯酸盐）对芳基烯烃进行自由基阳离子[4 + 2]环化，得到萘衍生物。在存在氧气（空气中）的情况下，两个烯烃分子的氧化二聚/分子内[4 + 2]环加成反应可提供3,4-二氢萘-1（2 H）-1 ，收率高至高。在氮气氛下，通过使用Selectfluor作为氧化剂，以中等至优异的产率获得了（二氢）萘。转型通过串联二聚体亲电加成/ Friedel-Crafts环化/自由基偶联/消除顺序。该方法表示使用可见光光催化级联策略温和而直接地组装萘骨架。
• A Succinct Synthesis of the Vaulted Biaryl Ligand Vanol via a Dienone-Phenol Rearrangement
  作者：Zhensheng Ding、Song Xue、William D. Wulff

  DOI：10.1002/asia.201000804

  日期：2011.8.1

  different approaches to the synthesis of 3‐phenyl‐1‐naphthol, a key intermediate in the synthesis of vanol. The first approach has its key step as the Michael addition of a benzyl Grignard to methyl cinnamate. In the second approach the key step is the first step, a Reformatsky reaction of ethyl bromoacetate and deoxybenzoin. The final and most‐efficient approach involves a dienone‐phenol rearrangement

  钒醇是拱形的配体联芳基家族的成员，并且已被证明在许多不对称催化反应中非常有效。先前的合成酚虽然有效，但受所涉及试剂成本的限制。本工作评估了三种合成3-苯基-1-萘酚的方法，3-萘-1-萘酚是合成薄荷醇的关键中间体。第一种方法的关键步骤是在肉桂酸甲酯上添加迈克尔·格利雅（Michael Grignard）苄基。在第二种方法中，关键步骤是第一步，即溴乙酸乙酯和脱氧安息香的Reformatsky反应。最终和最有效的方法涉及4-氯-1-萘酚与AlCl 3反应原位生成的4-芳基-1-四烯酮的二烯酮-苯酚重排 苯和苯，并报道了将该方法扩展至取代的芳醇衍生物的初步结果。
• Substituent-dependent electron-transfer-induced photooxygenation of 1,1-diarylethylenes
  作者：Klaus Gollnick、Albert Schnatterer、Gerald Utschick

  DOI：10.1021/jo00074a035

  日期：1993.10

  Rates and products of 9,10-dicyanoanthracene-sensitized photooxygenations of 1,1-diarylethylenes (1a-r) in acetonitrile were studied. If at least one of the aryl groups carries an electron-donating substituent at the para (or ortho) position (1a-1), 3,3,6,6-tetraaryl-1,2-dioxanes (2a-1) are generated in high yields (85-100%). Benzophenones (3) are the only other observable products. 1,1-Diphenylethylene (1n) and its m-methoxy (1m), p-chloro (1q,p), and p-nitro (1q,r) derivatives,however, yield mainly benzophenones (3m-r) (>50%) (the p-nitro compounds only in the presence of biphenyl). 1,2-Dioxanes (2m-p), cyclobutanes (4n-p), and alpha-tetralones (5m-o) are obtained as side products. Dioxanes, benzophenones, and alpha-tetralones are products of electron-transfer induced oxygenations involving triplet ground-state molecular oxygen, O-3(2). Singlet molecular oxygen, O2(1DELTA(g)),contributes to the benzophenone formation from strongly electron-donor substituted diarylethylenes. An exception is the most powerful electron-donor substituted diarylethylene 1a, with which O2(1DELTA(g)) undergoes an electron-transfer reaction affording dioxane 2a. Dioxane formation proceeds via free-radical cations 1.+, which enter into a chain reaction with 1, O-3(2), and another molecule of 1 to yield dioxane 2 and a new radical cation 1.+ that maintains the chain reaction. The efficiency of this chain process, however, is found to be several orders of magnitude smaller than expected. To explain this result, a 1,6-biradical.1-1-O2.is proposed to be generated in this chain reaction as the product-determining intermediate that predominantly fragments into O-3(2) and two molecules of 1. Cyclization to dioxane 2 and transformation to benzophenone 3 occur at presumably less than 0.1% from this biradical. The pathways leading to cyclobutanes (4) and alpha-tetralones (5) are also discussed.
• Repinskaya, I. B.; Savel'ev, V. A.; Makarova, Z. S., Journal of Organic Chemistry USSR (English Translation), 1980, p. 1463 - 1466
  作者：Repinskaya, I. B.、Savel'ev, V. A.、Makarova, Z. S.、Koptyug, V. A.

  DOI：——

  日期：——
• Repinskaya, I. B.; Barkhutova, D. D.; Makarova, Z. S., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, p. 759 - 767
  作者：Repinskaya, I. B.、Barkhutova, D. D.、Makarova, Z. S.、Alekseeva, A. V.、Koptyug, V. A.

  DOI：——

  日期：——