2,4-dimethyl-9H-fluoren-9-one | 2928-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,4-dimethyl-9H-fluoren-9-one
• 英文别名: 2,4-dimethylfluoren-9-one；2,4-dimethylfluorenone；2,4-Dimethyl-fluoren-9-on；2,4-Dimethyl-fluorenon；2,4-Dimethylfluorenon
• CAS: 2928-39-4
• 化学式: C₁₅H₁₂O
• mdl: MFCD00819794
• 分子量: 208.26
• InChiKey: ZJPLTNPWPGCPKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2,4-dimethyl-9H-fluoren-9-one 在 氢氧化钾 、 肼 作用下， 以 二乙二醇 为溶剂， 生成 2,4-dimethylfluorene
  参考文献：
  名称：

  Godfroid,J.-J., Bulletin de la Societe Chimique de France, 1964, p. 2929 - 2943

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3,5-dimethylbenzoyl)benzoic acid 在 dipotassium peroxodisulfate 、 silver(I) acetate 作用下， 以 氘代乙腈 为溶剂， 反应 1.0h， 以45%的产率得到2,4-dimethyl-9H-fluoren-9-one
  参考文献：
  名称：

  Decarboxylative C–H Arylation of Benzoic Acids under Radical Conditions

  摘要：

  A decarboxylative radical cyclization reaction has been developed for the synthesis of fluorenones. The reaction uses Ag(I)/K2S2O8 to oxidatively decarboxylate an aroylbenzoic acid to an aryl radical, which undergoes cyclization to afford fluorenone products in good yield.

  DOI：

  10.1021/ol3010694

文献信息

• Palladium Catalyzed Regioselective Cyclization of Arylcarboxylic Acids via Radical Intermediates with Diaryliodonium Salts
  作者：Guoqiang An、Limin Wang、Jianwei Han

  DOI：10.1021/acs.orglett.1c03016

  日期：2021.11.19

  Palladium-catalyzed C2-arylation/intramolecular acylation with arylcarboxylic acids was developed by using diaryliodonium salts. The protocol has the advantage of good step-economy by two chemical bonds formation in one pot.

  通过使用二芳基碘鎓盐开发了钯催化的 C 2 -芳基化/与芳基羧酸的分子内酰化。该协议的优点是在一锅中形成两个化学键，具有良好的阶梯经济性。
• Competition in intramolecular arylation of triphenylmethanols
  作者：Roger Bolton、Raphael S. Mguni、Gareth H. Williams

  DOI：10.1039/p29860000405

  日期：——

  following diazotisation and loss of nitrogen is determined by the nature of the intermediates formed. Where aryl radical intermediates are formed, the selectivity parallels that found in intermolecular competition by phenyl radicals, whereas copper-catalysed decomposition of the diazonium ion leads to intermediates which seem, from their selectivity, to possess considerable cationic nature. The slower thermal

  合成了六种新的2-氨基三苯基甲醇（1）的不对称取代衍生物。重氮化和氮损失后的闭环方向取决于所形成的中间体的性质。在形成芳基自由基中间体的情况下，选择性与在苯基分子间竞争中发现的平行，而铜催化的重氮离子的分解导致中间体从其选择性看来似乎具有相当大的阳离子性质。重氮离子的较慢的热分解出乎意料地显示出很小的选择性，表明静电相互作用在决定关键中间体的非常短的寿命中占主导地位。
• FLUORENE COMPOUND AND USE THEREOF FOR MEDICAL PURPOSES
  申请人：Japan Tobacco, Inc.

  公开号：EP2345629A1

  公开（公告）日：2011-07-20

  The present invention provides an agent for the prophylactic or treatment of diabetes, diabetic complications, insulin resistance syndrome, metabolic syndrome, hyperglycemia, dyslipidemia, atherosclerosis, cardiac failure, cardiomyopathy, myocardial ischemia, brain ischemia, cerebral apoplexy, pulmonary hypertension, hyperlactacidemia, mitochondrial disease, mitochondrial encephalomyopathy or cancer, namely, a PDHK inhibitor and the like. A compound represented by the following formula [I] or a pharmaceutically acceptable salt thereof, or a solvate thereof: wherein each symbol is as defined in the specification.

  本发明提供了一种用于预防或治疗糖尿病、糖尿病并发症、胰岛素抵抗综合征、代谢综合征、高血糖、血脂异常、动脉粥样硬化、心力衰竭、心肌病、心肌缺血、脑缺血、脑中风、肺动脉高压、高乳酸血症、线粒体疾病的制剂、心肌病、心肌缺血、脑缺血、脑中风、肺动脉高压、高乳酸血症、线粒体疾病、线粒体脑肌病或癌症，即 PDHK 抑制剂等。下式[I]代表的化合物或其药学上可接受的盐或其溶液： 其中各符号如说明书中所定义。
• Photoinduced C−Br Homolysis of 2-Bromobenzophenones and Pschorr Ring Closure of 2-Aroylaryl Radicals to Fluorenones
  作者：Jarugu Narasimha Moorthy、Subhas Samanta

  DOI：10.1021/jo7017872

  日期：2007.12.1

  [Graphics]A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl sigma-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl pi-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.
• Fluorenone Synthesis by Palladacycle-Catalyzed Sequential Reactions of 2-Bromobenzaldehydes with Arylboronic Acids
  作者：Tao-Ping Liu、Yuan-Xi Liao、Chun-Hui Xing、Qiao-Sheng Hu

  DOI：10.1021/ol200693d

  日期：2011.5.6

  A new, anionic four-electron donor-based (type I) palladacycle-catalyzed sequential reaction of 2-bromobenzaldehydes with arylboronic acids based on the addition reaction, cyclization via C-H activation-oxidation sequence is described. Our study provided an efficient access to a variety of substituted fluorenones/indenofluorenediones from readily available arylboronic acids and 2-bromobenzaldehydes.