ethyl 9-oxo-9H-fluorene-2-carboxylate | 860215-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ethyl 9-oxo-9H-fluorene-2-carboxylate
• 英文别名: ethyl 9-oxo-9H-fluorene-2-carboxlate；2-ethoxycarbonyl-9H-fluoren-9-one；9-oxo-fluorene-2-carboxylic acid ethyl ester；9-Oxo-fluoren-2-carbonsaeure-aethylester；9-Oxo-9H-fluorene-2-carboxylic acid ethyl ester；ethyl 9-oxofluorene-2-carboxylate
• CAS: 860215-06-1
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: YHFIZVLBMLLGNK-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142.5 °C
• 沸点：
  429.3±24.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 9-oxo-9H-fluorene-2-carboxylate 在 磷化氢 、 氢碘酸 、 溶剂黄146 作用下， 生成 9H-芴-2-羧基 酸
  参考文献：
  名称：

  Notes - Reduction of Fluorenonecarboxylic Acids to Fluorenecarboxylic Acids

  摘要：

  DOI：

  10.1021/jo01105a600
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 反应 8.0h， 生成 ethyl 9-oxo-9H-fluorene-2-carboxylate
  参考文献：
  名称：

  钯催化双CH活化和Heck环化反应由芳族醛肟肟醚和芳基卤化物合成芴酮。

  摘要：

  DOI：

  10.1002/anie.200804153

文献信息

• Synthesis of fluorenones viaquaternary ammonium salt-promoted intramolecular dehydrogenative arylation of aldehydes
  作者：Zhuangzhi Shi、Frank Glorius

  DOI：10.1039/c2sc21823b

  日期：——

  Biologically interesting fluorenone, xanthone and anthrone derivatives have been prepared via an intramolecular oxidative acylation process. This novel direct acylation reaction proceeded without the aid of any transition metals, acids or bases, and uses a catalytic amount of a quaternary ammonium salt in the presence of a persulfate oxidant. Initial mechanistic studies have been carried out to elucidate

  生物有趣 芴酮， 黄酮蒽酮衍生物是通过分子内氧化酰化方法制备的。这种新颖的直接酰化反应无需任何过渡金属，酸或碱即可进行，并在过硫酸盐氧化剂存在下使用催化量的季铵盐。已经进行了初步的机理研究以阐明反应途径。
• Synthesis and structure–activity relationships of new carbonyl guanidine derivatives as novel dual 5-HT2B and 5-HT7 receptor antagonists
  作者：Ayako Moritomo、Hiroyoshi Yamada、Toshihiro Watanabe、Hirotsune Itahana、Shinobu Akuzawa、Minoru Okada、Mitsuaki Ohta

  DOI：10.1016/j.bmc.2013.10.010

  日期：2013.12

  To identify potent dual 5-HT2B and 5-HT7 receptor antagonists, we synthesized a series of novel carbonyl guanidine derivatives and examined their structure–activity relationships. Among these compounds, N-(9-hydroxy-9H-fluorene-2-carbonyl)guanidine (10) had a good in vitro profile, that is, potent affinity for human 5-HT2B and 5-HT7 receptor subtypes (Ki = 1.8 nM and Ki = 17.6 nM, respectively) and

  为了鉴定有效的双重5-HT 2B和5-HT 7受体拮抗剂，我们合成了一系列新型羰基胍衍生物，并研究了它们的结构-活性关系。在这些化合物中，N-（9-羟基-9 H-芴-2-羰基）胍（10）具有良好的体外特性，即对人5-HT 2B和5-HT 7受体亚型的有效亲和力（ķ我 = 1.8纳米和ķ我 = 17.6纳米，）和高选择性超过5-HT 2A，5-HT 2C，α 1，d 2和M 1受体。当口服时，化合物10还对豚鼠的5-HT诱导的硬脑膜蛋白渗出具有抑制作用。
• Structural influences impacting the role of the 9-ylidene bond in the electronic tuning of structures built upon 9-fluorenylidene scaffolds
  作者：Galen L. Eakins、Matthew W. Cooper、Nikolay N. Gerasimchuk、Terry J. Phillips、Bryan E. Breyfogle、Chad J. Stearman

  DOI：10.1139/cjc-2013-0074

  日期：2013.11

  A structure–effect study is presented pertaining to the HOMO–LUMO tuning of compounds built upon the 9-fluorenylidene scaffold frequently incorporated as a moiety within organic-based semiconducting materials. The results represent the first reported analysis employing an ensemble of spectroscopy, electrochemistry, and crystal structure data to elucidate and compare the electronic properties of 9-fluorenones, 9-fluorenylidenes, and 9-fluorenimine derivatives. The results also provide the first spectroscopically and crystallographically measured description of exciton coupling within 9,9′-bifluorenylidenes. The 9-ylidene bond is seen to play a key role impacting the electronic properties, and an examination of the effects of substituents, conjugation, heteroatoms, and steric strain on the 9-ylidene bond in a diverse set of structures with representative structural variations relevant to the HOMO–LUMO tuning is presented. Increasing conjugation decreased the HOMO–LUMO gap (HLG), increased the HOMO energy (E_HOMO), but decreased the LUMO energy (E_LUMO). Substituent effects were observed to produce only slight changes that tended to decrease the HLG and increase both E_HOMO and E_LUMO, while heteroatom inclusion at the 9-ylidine bond tended to decrease the HLG, E_HOMO, E_LUMO, and the extinction coefficient. In the sterically hindered 9,9′-bifluorenylidenes, increased steric strain that promoted either an increase in the torsion angle or bond length of the 9-ylidene bond was seen to decrease the HLG via exciton coupling. These results elucidate the HOMO–LUMO tuning of systems containing a 9-fluorenylidene moiety and may assist in developing materials with specifically tuned HLGs and HOMO–LUMO levels for a variety of applications.

  本文介绍了一项结构-效应研究，涉及到建立在9-芴亚甲基骨架上的化合物的HOMO-LUMO调节。该骨架经常被作为有机半导体材料中的一部分。结果是第一个使用光谱学，电化学和晶体结构数据来阐明和比较9-芴酮，9-芴亚甲基和9-芴亚胺衍生物的电子性质的分析。结果还提供了第一个获得9,9'-双芴亚甲基激子耦合的光谱和晶体学测量描述。 9-亚甲基键被看作是影响电子性质的关键因素，并且对于具有代表性的结构变化的多样化结构集合，对取代基，共轭，杂原子和立体位阻对9-亚甲基键的影响进行了研究。增加共轭减少了HOMO-LUMO间隙（HLG），增加了HOMO能量（EHOMO），但降低了LUMO能量（ELUMO）。观察到取代基效应只会产生轻微的变化，倾向于减少HLG并增加E_HOMO和E_LUMO，而在9-亚甲基酰胺键中包含杂原子倾向于降低HLG，E_HOMO，E_LUMO和消光系数。在立体位阻的9,9'-双芴亚甲基中，通过激子耦合，促进9-亚甲基键的扭转角度或键长的增加，可降低HLG。这些结果阐明了含有9-芴亚甲基基团的系统的HOMO-LUMO调节，并可能有助于开发具有特定调节HLG和HOMO-LUMO水平的材料，以用于各种应用。
• 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。
• The Structure of Fluorene¹
  作者：John H. Weisburger、Elizabeth K. Weisburger、Francis Earl Ray

  DOI：10.1021/ja01165a118

  日期：1950.9