1,2,3-trimethoxy-9H-fluoren-9-one | 1433967-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1,2,3-trimethoxy-9H-fluoren-9-one
• 英文别名: 1,2,3-Trimethoxyfluoren-9-one；1,2,3-trimethoxyfluoren-9-one
• CAS: 1433967-23-7
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: GBKVOJRRIWVRTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氰基苯硼酸 在 双(乙腈)氯化钯(II) 、 tripotassium phosphate "n" hydrate 、 Pd(PPh₃)₂Cl₂ 、 水 、 silver trifluoroacetate 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 、 三氟乙酸 为溶剂， 反应 86.0h， 生成 1,2,3-trimethoxy-9H-fluoren-9-one
  参考文献：
  名称：

  Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation

  摘要：

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

  DOI：

  10.1021/ol401063w

文献信息

• Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone
  作者：Ilya A P Jourjine、Lukas Zeisel、Jürgen Krauß、Franz Bracher

  DOI：10.3762/bjoc.17.181

  日期：——

  Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further

  通过不含金属和添加剂的 TBHP 促进的易于获得的N-甲基-2-(氨甲基)联苯和 2-(氨甲基)联苯的交叉脱氢偶联 (CDC)，可以轻松制备高度取代的芴酮，收率基本上相当到良好。该方法与多种官能团（甲氧基、氰基、硝基、氯以及苯酚的 SEM 和 TBS 保护基团）兼容，并进一步用于天然产物诺比隆的首次全合成。
• Benzene-Free Synthesis of Multisubstituted Catechol via Oxidative Dearomatic Reorganization
  作者：Tongxiang Cao、Qiu Shi、Shifa Zhu

  DOI：10.1021/acs.orglett.1c00071

  日期：2021.2.19

  multisubstituted catechol via an oxidative dearomatic reorganization is reported. This reaction tolerated a wide spectrum of functionalities, which could be applied in the synthesis of an electron-deficient arene-conjugated catechol that is difficult to access via biomimetic oxidative coupling. In addition, a diversification-oriented transformation that leveraged the versatile catechol afforded a series

  报道了通过氧化脱芳基重组无苯合成多取代邻苯二酚。该反应具有广泛的功能，可用于合成难以通过仿生氧化偶联获得的缺电子芳烃共轭邻苯二酚。此外，利用多功能儿茶酚的多元化转型提供了一系列功能丰富的产品。
• 儿茶酚类化合物及其制备方法和应用
  申请人：心远（广州）药物研究有限公司

  公开号：CN112961041B

  公开（公告）日：2022-06-21

  本发明提供儿茶酚类化合物及其制备方法和应用。该类儿茶酚类化合物具有式(Ⅰ)或式(Ⅲ)结构。本发明还公开所述儿茶酚类化合物的制备方法，该方法原料来源广泛，操作简单，路线简短，无需金属催化，成本低，有潜在工业化的价值。本发明所述儿茶酚类化合物具备抑制PC3人前列腺癌细胞增殖的活性，因此可以用于制备抗前列腺癌药物。
• Direct Excitation of Aldehyde to Activate the C( <i>sp</i> ^<i>2</i> )−H Bond by Cobaloxime Catalysis toward Fluorenones Synthesis with Hydrogen Evolution
  作者：Jia‐Dong Guo、Ya‐Jing Chen、Chen‐Hong Wang、Qiao He、Xiu‐Long Yang、Tian‐Yu Ding、Ke Zhang、Rui‐Nan Ci、Bin Chen、Chen‐Ho Tung、Li‐Zhu Wu

  DOI：10.1002/anie.202214944

  日期：2023.2.6

  highly reactive photoexcited triplet state of aromatic aldehyde intermediates is intercepted by the catalyst in the ground state, thus leading to the synthesis of a series of fluorenones, xanthones and thioxanthones in good to excellent yields without any external oxidants and with hydrogen as the byproduct.

  已经成功开发了通过钴肟催化直接激发醛以激活其 C ( sp 2 )-H 键。在照射下，芳香醛中间体的高反应性光激发三重态被基态催化剂拦截，从而导致在没有任何外部氧化剂和氢作为副产品。
• Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation
  作者：Jung-Chih Wan、Jun-Min Huang、Yu-Huei Jhan、Jen-Chieh Hsieh

  DOI：10.1021/ol401063w

  日期：2013.6.7

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.