1,4-双(2-萘基)-1,4-丁二酮 | 34733-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,4-双(2-萘基)-1,4-丁二酮
• 英文名称: 1,4-di(2-naphthyl)-1,4-butanedione
• 英文别名: 1,4-di(naphthalen-2-yl)butane-1,4-dione；1,4-Bis(naphthalen-2-yl)butane-1,4-dione；1,4-dinaphthalen-2-ylbutane-1,4-dione
• CAS: 34733-57-8
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: CPKCEHISBAJKEC-UHFFFAOYSA-N

物化性质

• 沸点：
  576.0±33.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1,4-双(2-萘基)-1,4-丁二酮 在 (1R,2R)-β-ketoiminato cobalt(II) sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 74.5h， 生成 methanesulfonic acid 4-methanesulfonyloxy-1,4-di-naphthalen-2-yl-butyl ester
  参考文献：
  名称：

  Sato, Mitsuo; Gunji, Yasuhiko; Ikeno, Taketo, Synthesis, 2004, # 9, p. 1434 - 1438

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴代-2-乙酰基萘 在 rongalite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60%的产率得到1,4-双(2-萘基)-1,4-丁二酮
  参考文献：
  名称：

  铜（I）/ DDQ介导的芳基丁烯与1,4-二酮和吲哚酮的双脱氢Diels-Alder反应。

  摘要：

  首次建立了由铜（I）/ DDQ介导的简单丁烯与1,4-二酮和吲哚酮的双脱氢Diels-Alder（DDDA）反应。此策略基于非预官能化原料的串联双脱氢/ Diels-Alder反应，其中通过在一个催化系统中活化四重惰性C（sp 3）-H键原位生成二烯和亲二烯体。

  DOI：

  10.1021/acs.orglett.0c02486

文献信息

• Synthesis of 1,4-Diketones via Titanium-Mediated Reductive Homocoupling of α-Haloketones
  作者：Michael Gesinski、Nathan Le、Aimee Rodriguez、James Alleyn

  DOI：10.1055/s-0037-1610245

  日期：2018.10

  1,4-Diketones have been synthesized via a reductive homocoupling of α-haloketones. Addition of a Grignard reagent to titanium(IV) isopropoxide affords a low-valent titanium(III) intermediate that is believed to mediate a radical dimerization reaction. The reaction works well for a variety of aromatic α-haloketones including heteroaromatic compounds.

  1,4-二酮是通过 α-卤代酮的还原同偶联合成的。将格氏试剂添加到异丙醇钛 (IV) 中会得到一种低价钛 (III) 中间体，据信该中间体可介导自由基二聚反应。该反应适用于各种芳族 α-卤代酮，包括杂芳族化合物。
• Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes
  作者：Xiaolin Zhu、Yixiong Lin、Yue Sun、Matthew C. Beard、Yong Yan

  DOI：10.1021/jacs.8b08720

  日期：2019.1.16

  Cost-effective and efficient photocatalysis are highly desirable in chemical synthesis. Here we demonstrate that readily prepared suspensions of APbBr3 (A = Cs or methylammonium (MA)) type perovskite colloids (ca. 2-100 nm) can selectively photocatalyze carbon-carbon bond formation reactions, i.e., α-alkylations. Specifically, we demonstrate α-alkylation of aldehydes with a turnover number (TON) of

  在化学合成中非常需要具有成本效益和高效的光催化。在这里，我们证明容易制备的 APbBr3（A = Cs 或甲基铵（MA））型钙钛矿胶体（约 2-100 nm）悬浮液可以选择性地光催化碳-碳键形成反应，即α-烷基化。具体来说，我们展示了醛的 α-烷基化，在可见光照射下，周转数 (TON) 超过 52,000。混合有机/无机钙钛矿正在彻底改变光伏研究，现在正在影响其他研究领域，但它们在有机合成方面的探索很少见。我们的低成本、易于加工、高效且能带可调的钙钛矿光催化剂有望为化学合成带来新的见解。
• Synthesis of 1,4-diketones: reaction of α-bromo ketones with tetrakis(dimethylamino)ethylene (TDAE)
  作者：Yutaka Nishiyama、Akihiro Kobayashi

  DOI：10.1016/j.tetlet.2006.05.141

  日期：2006.7

  1,4-Diketones were prepared by the reaction of α-bromo ketones with tetrakis(dimethylamino)ethylene (TDAE) in moderate to good yields. Similarly, α-bromo esters were reductively coupled using TDAE to give the 1,4-diesters in moderate yields.

  通过使α-溴代酮与四（二甲基氨基）乙烯（TDAE）反应，以中等至良好的产率制备1,4-二酮。类似地，使用TDAE将α-溴代酯还原偶联，以中等收率得到1，4-二酯。
• Exploratory Studies of H-Atom Abstraction and Silyl-Transfer Photoreactions of Silylalkyl Ketones and (Silylalkyl)phthalimides
  作者：Yean Jang Lee、Rong Ling、Patrick S. Mariano、Ung Chan Yoon、Dong Uk Kim、Sun Wha Oh

  DOI：10.1021/jo9522623

  日期：1996.1.1

  Exploratory studies have been conducted to probe competitive H-atom abstraction and SET-promoted, silyl-transfer reactions of excited states of silylalkyl ketones and (silylalkyl)phthalimides. Photochemical investigations with the (silylalkyl)phthalimides have demonstrated that typical gamma-H atom abstraction reactions occur upon irradiation in less polar and less silophilic solvents. In contrast, irradiation of these substances in polar-protic-silophilic solvents results in product formation via pathways involving SET-induced desilylation. Photoreactions of silylamido-aryl ketones in either nonsilophilic or silophilic solvents take place almost exclusively by sequential SET silyl-transfer routes to produce azetidine products. Finally, the chemical selectivities of photochemical reactions of silylpropyl-aryl ketones appear to depend on medium polarity and silophilicity. Irradiation of these substrates in less polar-nonsilophilic solvents leads to almost exclusive formation of acetophenone and vinyltrimethylsilane in essentially equal yields by a reaction pathway initiated by gamma-H atom abstraction and 1,4-biradical fragmentation. However, irradiation of these substances in polar-silophilic solvents produces acetophenone and vinyltrimethylsilane in an ca. 1.7:1 ratio reflecting the fact that a silyl-transfer pathway competes with H-atom abstraction under these conditions.
• The operation of H-atom and TMS-group transfer processes in the photochemistry of silylamidoalkyl- and silylalkyl-ketones and -phthalimides
  作者：Yean Jang Lee、Chao Pin Lee、Yoon Tag Jeon、Patrick S. Mariano、Ung Chan Yoon、Dong Uk Kim、Jack C. Kim、Jong Gun Lee

  DOI：10.1016/s0040-4039(00)73797-x

  日期：1993.9