3-(9H-xanthen-9-yl)pentane-2,4-dione | 106917-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(9H-xanthen-9-yl)pentane-2,4-dione
• 英文别名: Pentane-2,4-dione, 3-(9H-xanthen-9-yl)-
• CAS: 106917-00-4
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: OEPKUNSAGYMPDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  3-(9H-xanthen-9-yl)pentane-2,4-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以94%的产率得到9-(diacetylmethylene)xanthene
  参考文献：
  名称：

  Manganese(III)-mediated carbon-carbon bond formation in the reaction of xanthenes with active methylene compounds

  摘要：

  Oxidation of xanthenes with manganese(III) acetate in the presence of active methylene compounds such as 1,3-dicarbonyl compounds, malononitrile derivatives, acetone, and nitromethane selectively gives 9-substituted xanthene derivatives in good yields. A similar oxidation of thioxanthene also yields 2-(9-thioxanthenyl)-1,3-dicarbonyl compounds in 57-91% yields. The obtained 2-(9-xanthenyl)-1,3-dicarbonyl compounds are readily converted to 2-(9-xanthenylidene)-1,3-dicarbonyl derivatives using manganese(III) complexes or 2,3-dichloro-5, 6-dicyano-1,4-benzoquinone. The mechanisms for the formation of 9-substituted xanthenes are discussed on the basis of the reaction of intermediates, the electron-donating substituent effect on the xanthene ring system, effect of additives, and comparison with a reaction of radical-trapping reagents.

  DOI：

  10.1021/jo00039a010
• 作为产物：
  描述：

  氧杂蒽 、 乙酰丙酮 在 甲烷磺酸 、 氧气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、6.0 MPa 条件下， 反应 48.0h， 以33%的产率得到3-(9H-xanthen-9-yl)pentane-2,4-dione
  参考文献：
  名称：

  氧气分压升高时磺酸催化的自氧化碳-碳偶联反应

  摘要：

  描述了苄基CH键与各种C-亲核试剂的好氧有机催化氧化CC键形成反应。通过在室温下在磺酸催化剂的存在下在升高的氧分压下简单地搅拌底物来进行偶联反应。压力的升高使得广泛范围的亲核底物能够反应，否则在环境压力下显示出较差的反应性。苄Ç 呫吨，acridanes，isochromane及相关杂环的H键可以与亲核试剂包括酮，1,3-二羰基化合物和醛官能化。富电子芳烃可在高温下用作亲核试剂。该反应被认为是通过以下方式进行的苄基CH键的自氧化与氢过氧化物和随后被磺酸催化的亲核取代。

  DOI：

  10.1002/adsc.201100563

文献信息

• Biocompatible ionic liquid [Betaine][H₂PO₄] as a reusable catalyst for the substitution of xanthen-9-ol under solvent-free conditions
  作者：Anlian Zhu、Tong Wang、Wanlu Feng、Jianji Wang、Lingjun Li

  DOI：10.1039/d0ra05374k

  日期：——

  An ionic liquid, namely [Betaine][H2PO4], was found to be an efficient catalyst for the direct substitution reaction of xanthen-9-ol with different nucleophiles under solvent-free conditions. This catalytic system is easy to be operated and the following work-up procedure is simple, with the ionic liquid catalyst reusable for at least five cycles at a high catalytic activity level. In addition, the

  离子液体，即[甜菜碱][H 2 PO 4 ]，被发现是无溶剂条件下xanthen-9-ol与不同亲核试剂直接取代反应的有效催化剂。该催化体系易于操作，后续后处理程序简单，离子液体催化剂可在高催化活性水平下重复使用至少五个循环。此外，离子液体制备简单，原料廉价，生物相容性好。因此，我们的研究提出了一种有趣且可持续的直接替代酒精的方案。
• Direct Diacetylmethylation of Aromatic Compounds with Tris(2,4-pentanedionato)manganese(III)
  作者：Hiroshi Nishino

  DOI：10.1246/bcsj.59.1733

  日期：1986.6

  diacetylmethylene derivatives which were further oxidized. It was found that this direct diacetylmethylation was effective when the ionization potential of the aromatic compound was lower than 8.12 eV, and that the diacetylmethyl radical which was generated directly by the thermolysis of tris(2,4-pentanedionato)manganese(III) has an electrophilic nature based on the result of the oxidation of substituted

  在乙酸中用三(2,4-戊二酮基)锰(III)氧化萘以良好至中等产率得到二乙酰甲基衍生物。使用过量的氧化剂，乙酰甲基取代的萘被进一步氧化，得到 3-乙酰氧基-3-萘基-2,4-戊二酮。蒽的类似氧化也产生（二乙酰甲基）蒽以及进一步氧化的二乙酰亚甲基衍生物。发现当芳香族化合物的电离电位低于 8.12 eV 时，这种直接二乙酰甲基化是有效的，并且由三（2,4-戊二酮）锰（III）热解直接产生的二乙酰甲基自由基具有基于取代萘氧化的结果的亲电性。
• Iodine-catalyzed efficient synthesis of xanthene/thioxanthene-indole derivatives under mild conditions
  作者：Weihang Miao、Pingting Ye、Mengjiao Bai、Zhixin Yang、Suyue Duan、Hengpan Duan、Xuequan Wang

  DOI：10.1039/d0ra05217e

  日期：——

  xanthen-9-ol and thioxanthen-9-ol with indoles has been developed, providing an efficient procedure for the synthesis of xanthene/thioxanthene-indole derivatives with good to excellent yields. This protocol offers several advantages, such as short reaction times, green solvent, operational simplicity, easily available catalyst and mild reaction conditions. Moreover, this method showed good tolerance of functional

  开发了一种碘催化的呫吨-9-醇和噻吨-9-醇与吲哚的亲核取代反应，为合成呫吨/噻吨-吲哚衍生物提供了一种有效的方法，且收率良好。该方案具有反应时间短、溶剂绿色、操作简单、催化剂易得和反应条件温和等优点。此外，该方法对官能团和多种底物表现出良好的耐受性。
• Sulfonic Acid-Catalyzed Autoxidative Carbon-Carbon Coupling Reaction under Elevated Partial Pressure of Oxygen
  作者：Áron Pintér、Martin Klussmann

  DOI：10.1002/adsc.201100563

  日期：2012.3

  reactivity at ambient pressure. The benzylic CH bonds of xanthene, acridanes, isochromane and related heterocycles could be functionalized with nucleophiles including ketones, 1,3‐dicarbonyl compounds and aldehydes. Electron‐rich arenes could be utilized as nucleophiles at elevated temperatures. The reactions are believed to proceed via autoxidation of the benzylic CH bonds to the hydroperoxides and subsequent

  描述了苄基CH键与各种C-亲核试剂的好氧有机催化氧化CC键形成反应。通过在室温下在磺酸催化剂的存在下在升高的氧分压下简单地搅拌底物来进行偶联反应。压力的升高使得广泛范围的亲核底物能够反应，否则在环境压力下显示出较差的反应性。苄Ç 呫吨，acridanes，isochromane及相关杂环的H键可以与亲核试剂包括酮，1,3-二羰基化合物和醛官能化。富电子芳烃可在高温下用作亲核试剂。该反应被认为是通过以下方式进行的苄基CH键的自氧化与氢过氧化物和随后被磺酸催化的亲核取代。
• The direct substitutions of 9H-xanthen-9-ol with indoles in a room temperature ionic liquid medium BmimBF4
  作者：Ling-yan Liu、Bing Wang、Hong-mei Yang、Wei-xing Chang、Jing Li

  DOI：10.1016/j.tetlet.2011.08.085

  日期：2011.10

  simple, atom economical, highly efficient and green protocol has been developed for the SN1-type substitutions of 9H-xanthen-9-ol with indoles or other nucleophiles (such as diketone and pyrrole). This approach provides the substitution products in high or excellent yields in the BmimBF4 media at room temperature.

  已经开发出一种简单，原子经济，高效且绿色的方案，用于用吲哚或其他亲核试剂（例如二酮和吡咯）将9 H-黄嘌呤-9-ol进行S N 1型取代。在室温下，该方法可在BmimBF 4培养基中以高收率或优异的收率提供替代产品。