[2,2'-binaphthalene]-1,4-dione | 71506-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [2,2'-binaphthalene]-1,4-dione
• 英文别名: 2-Naphthalen-2-ylnaphthalene-1,4-dione
• CAS: 71506-28-0
• 化学式: C₂₀H₁₂O₂
• 分子量: 284.314
• InChiKey: QNLNLNBHEPRDSH-UHFFFAOYSA-N

物化性质

• 沸点：
  504.2±50.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  [2,2'-binaphthalene]-1,4-dione 在 氢氧化钾 作用下， 生成 4-hydroxy-3-naphthalen-2-ylnaphthalene-1,2-dione
  参考文献：
  名称：

  Chattaway, Journal of the Chemical Society, 1895, vol. 67, p. 657

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘萘 在 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 [2,2'-binaphthalene]-1,4-dione
  参考文献：
  名称：

  Transition Metal-Free Direct C–H Functionalization of Quinones and Naphthoquinones with Diaryliodonium Salts: Synthesis of Aryl Naphthoquinones as β-Secretase Inhibitors

  摘要：

  A novel ligand-free, transition metal-free direct C-H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.

  DOI：

  10.1021/jo501467v

文献信息

• Synthesis of Functionalized Dihydrocoumarins by NHC-Catalyzed [3 + 3] Annulation of Enals with 2-Substituted Naphthoquinones
  作者：Sayan Shee、Soumen Barik、Arghya Ghosh、Akkattu T. Biju

  DOI：10.1021/acs.orglett.1c03059

  日期：2021.10.15

  The [3 + 3] annulation of α,β-unsaturated aldehydes with 2-substituted 1,4-naphthoquinones allowing the facile synthesis of functionalized dihydrocoumarins catalyzed by N-heterocyclic carbene (NHC) is reported. The initially formed NHC-homoenolates underwent an efficient Michael–isomerization–lactonization cascade to furnish the products. Preliminary studies on mechanism shed light on the homoenolate

  据报道，α,β-不饱和醛与 2-取代的 1,4-萘醌的 [3 + 3] 环化可以轻松合成由 N-杂环卡宾 (NHC) 催化的功能化二氢香豆素。最初形成的 NHC-homoenolates 经历了有效的迈克尔 - 异构化 - 内酯化级联以提供产品。对机制的初步研究揭示了 α,β-不饱和酰基唑中间体中间体的同烯醇化物途径。此外，使用手性 NHC，所需产物的产率高达 49%，比价为 99:1。
• Mn-Catalyzed 1,6-conjugate addition/aromatization of <i>para</i>-quinone methides
  作者：Bobin Yang、Wei Yao、Xiao-Feng Xia、Dawei Wang

  DOI：10.1039/c8ob01057a

  日期：——

  A series of ferrocenyl triazole ligands have been synthesized and characterized, which proved to be effective for the Mn-catalyzed 1,6-conjugate addition/aromatization of para-quinone methides.

  一系列二茂铁三唑配体已被合成和表征，证明对锰催化的1,6-共轭加成/芳构化反应具有有效性，该反应针对对醌亚甲基。
• Synthesis of Aryl- and Alkylquinones through Rhodium-Catalyzed C–C ­Coupling under Mild Conditions
  作者：Dawei Wang、Yuqiang Ding、Bingyang Ge、Liyong Du、Hongyan Miao

  DOI：10.1055/s-0034-1379472

  日期：——

  A direct arylation, alkylation of quinones with aryl and alkyl boronic acids through rhodium-catalyzed C-C coupling has been developed under mild conditions. [Cp*RhCl2](2) was shown to be the most effective catalyst for the transformation. More importantly, good to excellent yields were obtained under room temperature and base-free conditions. This reaction provides a practical, efficient method for the synthesis of aryl- and alkylquinones.
• XIV.—On certain derivatives of isodinaphthyl
  作者：Adolf Staub、Watson Smith

  DOI：10.1039/ct8854700104

  日期：——