1,1-dibenzyl-1,2-dihydronaphthalen-2-one | 74849-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1-dibenzyl-1,2-dihydronaphthalen-2-one
• 英文别名: 1,1-dibenzyl-2(1H)-naphthalenone；1,1-Dibenzyl-2(1H)-naphthalinon；1,1-Dibenzyl-2(1)-naphthalenon；1,1-Dibenzyl-naphthalen-on-(2)；1,1-Dibenzylnaphthalen-2(1H)-one；1,1-dibenzylnaphthalen-2-one
• CAS: 74849-12-0
• 化学式: C₂₄H₂₀O
• 分子量: 324.422
• InChiKey: QQHAKFWQVIIKGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-dibenzyl-1,2-dihydronaphthalen-2-one 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以77%的产率得到3-bromo-1,1-dibenzyl-2(1H)-naphthalenone
  参考文献：
  名称：

  Novel rearrangement and cyclization processes resulting from bromination of 1,1-dibenzyltetralin derivatives

  摘要：

  Addition of bromine to hydrocarbon 1 results in an aromatic alkylation to form the bicyclo[3.3.1]nonane derivative 5. Addition of bromine to ketone 3 in acetonitrile solution results in a dienone-phenol rearrangement to form phenol 6, while reaction of ketone 4 with phosphorus pentabromide yields phenols 10 and 11. This reaction results from a novel ''bromo ketone-phenol'' rearrangement, as demonstrated by the fact that bromo ketones 12 and 13 spontaneously isomerize to 10 and 11.

  DOI：

  10.1021/jo00032a015
• 作为产物：
  描述：

  1,1-dibenzyl-3,4-dihydronaphthalen-2(1H)-one 生成 1,1-dibenzyl-1,2-dihydronaphthalen-2-one
  参考文献：
  名称：

  Novel rearrangement and cyclization processes resulting from bromination of 1,1-dibenzyltetralin derivatives

  摘要：

  Addition of bromine to hydrocarbon 1 results in an aromatic alkylation to form the bicyclo[3.3.1]nonane derivative 5. Addition of bromine to ketone 3 in acetonitrile solution results in a dienone-phenol rearrangement to form phenol 6, while reaction of ketone 4 with phosphorus pentabromide yields phenols 10 and 11. This reaction results from a novel ''bromo ketone-phenol'' rearrangement, as demonstrated by the fact that bromo ketones 12 and 13 spontaneously isomerize to 10 and 11.

  DOI：

  10.1021/jo00032a015

文献信息

• Regioselectivity of the alkylation of ambident anionic species on alumina or in the presence of ‘solid hexamethylphosphoric triamide’
  作者：Georges Bram、Niall Geraghty、Gérard Nee、Jacqueline Seyden-Penne

  DOI：10.1039/c39800000325

  日期：——

  C-Alkylation of the acetoacetate anions and of sodium naphthoxide is highly favoured on alumina, while O-alkylation of the acetoacetate anion predominates in tetrahydrofuran in the presence of solid hexamethylphosphoric triamide.

  在氧化铝上，乙酰乙酸根阴离子和萘氧基钠的C-烷基化是非常有利的，而乙酰乙酸根阴离子的O-烷基化在四氢呋喃中在固体六甲基磷酸三酰胺存在下占优势。
• Synthesis, X-ray crystal structure, and solid-state blue fluorescence of dialkylbenzo[b]naphtho[2,1-d]furan-6-one-type fluorophores
  作者：Yousuke Ooyama、Haruka Egawa、Toshiki Mamura、Katsuhira Yoshida

  DOI：10.1016/j.tet.2008.05.067

  日期：2008.7

  and in solid state, the fluorescence quantum yields (Φ) are almost the same among 2a–2c (Φsolution=∼0.5 and Φsolid=∼0.4). Interestingly, the fluorophore 2a exhibits strong blue fluorescence emission both in solution and in crystalline state. To elucidate the effects of the dialkyl substituents on solid-state photophysical properties, we performed time-resolved fluorescence spectroscopic measurement

  新型固体发射苯并[ b ]萘[2,1 - d ]呋喃-6-型荧光团2a – 2c，具有π平面发色团骨架和位阻二烷基取代基（R =丁基，辛基和苄基） ）设计并易于合成。在环己烷和固态下，荧光量子产率（Φ）在2a – 2c之间几乎相同（Φ溶液=〜0.5，Φ固体=〜0.4）。有趣的是，荧光团2a在溶液和结晶状态下均显示出强烈的蓝色荧光发射。为了阐明二烷基取代基对固态光物理性质的影响，我们进行了时间分辨荧光光谱测量，半经验分子轨道计算（AM1和INDO / S）以及X射线晶体学分析。
• Highly selective benzylations of β-naphthoxide anion in heterogeneous media
  作者：G. Bram、A. Loupy、J. Sansoulet、F. Vaziri-Zand

  DOI：10.1016/s0040-4039(01)91111-6

  日期：1984.1
• Nuclear Alkylation of Salts of Naphthols and Anthranol¹
  作者：DAVID Y. CURTIN、RICHARD C. TUITES、DOUGLAS H. DYBVIG

  DOI：10.1021/jo01072a001

  日期：1960.2
• Influence of phase transfer catalyst structure on selectivity
  作者：E. V. Dehmlow

  DOI：10.1007/bf00696697

  日期：1995.11

  A concise review is given of systematic studies concerned with the tuning of regio-, ''frequentio-,'' chemo-, and diastereoselectivity by the structure or type of phase transfer catalyst.