3-ethyl-9H-xanthen-9-one | 91483-11-3

• 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-ethyl-9H-xanthen-9-one
• 英文别名: 3-ethylxanthen-9-one
• CAS: 91483-11-3
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: ODXCRAAJULACQN-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  375.6±32.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethyl-9H-xanthen-9-one 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 9.0h， 生成 3-(1-(acetyloxy)ethyl)-9H-xanthen-9-one
  参考文献：
  名称：

  Photochemistry of the 9-Hydroxyxanthenyl Radical in the Laser-Jet: Evidence for Photochemically Induced, Regioselective Radical Coupling

  摘要：

  The conventional irradiation (low intensity) of xanthone in ethanol was observed to produce pinacol 3 by photoreductive coupling and 9-hydroxy-9-(1-hydroxyethyl)-9H-xanthene (4) by head-to-head cross-coupling between the resultant 9-hydroxyxanthenyl (2) and 1-hydroxyethyl radicals. Under laser-jet conditions (high intensity), in addition to products 3 and 4, 3-(1-hydroxyethyl)-9H-xanthen-9-one (5d) was obtained as the major head-to-tail cross-coupling product. The observed dependence of the product ratio of 4 and 5d on the irradiation intensity is rationalized in terms of the higher spin density in the aryl rings, particularly at the 3-position (para to the hydroxy-substituted carbon atom), of the electronically excited 9-hydroxyxanthenyl radical (2'). For the ground state radical 2, as expected, the majority of spin density resides at the hydroxy-substituted carbon atom and, thus, constitutes the precursor to the head-to-head cross-coupling product 4. The theoretical spin densities for the ground and excited state 9-hydroxyxanthenyl radicals 2, calculated by semiempirical MO methods (PM3), indicate that upon photoexcitation the electron density in the SOMO shifts from the hydroxy-substituted radical center (ground state) to the aromatic pi-system (first excited state) and is concentrated at the 1a- and 3-positions.

  DOI：

  10.1021/ja00088a002
• 作为产物：
  描述：

  3-乙基苯酚 、 2-氯苯甲酸 在 硫酸 、 铜 、 potassium carbonate 、 copper(II) iodide 作用下， 生成 3-ethyl-9H-xanthen-9-one 、 1-ethyl-9H-xanthen-9-one
  参考文献：
  名称：

  Photochemistry of the 9-Hydroxyxanthenyl Radical in the Laser-Jet: Evidence for Photochemically Induced, Regioselective Radical Coupling

  摘要：

  The conventional irradiation (low intensity) of xanthone in ethanol was observed to produce pinacol 3 by photoreductive coupling and 9-hydroxy-9-(1-hydroxyethyl)-9H-xanthene (4) by head-to-head cross-coupling between the resultant 9-hydroxyxanthenyl (2) and 1-hydroxyethyl radicals. Under laser-jet conditions (high intensity), in addition to products 3 and 4, 3-(1-hydroxyethyl)-9H-xanthen-9-one (5d) was obtained as the major head-to-tail cross-coupling product. The observed dependence of the product ratio of 4 and 5d on the irradiation intensity is rationalized in terms of the higher spin density in the aryl rings, particularly at the 3-position (para to the hydroxy-substituted carbon atom), of the electronically excited 9-hydroxyxanthenyl radical (2'). For the ground state radical 2, as expected, the majority of spin density resides at the hydroxy-substituted carbon atom and, thus, constitutes the precursor to the head-to-head cross-coupling product 4. The theoretical spin densities for the ground and excited state 9-hydroxyxanthenyl radicals 2, calculated by semiempirical MO methods (PM3), indicate that upon photoexcitation the electron density in the SOMO shifts from the hydroxy-substituted radical center (ground state) to the aromatic pi-system (first excited state) and is concentrated at the 1a- and 3-positions.

  DOI：

  10.1021/ja00088a002

文献信息

• Acid- and radical-generating agent and method for generating acid and radical
  申请人：FUJIFILM Wako Pure Chemical Corporation

  公开号：US10451967B2

  公开（公告）日：2019-10-22

  It is a subject of the present invention to provide an acid- and radical-generating agent which has high sensitivity to an active energy ray having a wavelength of around 300 to 450 nm, and can exert both high acid-generating performance and high radical-generating performance, and has heat resistance; and a method for generating an acid and a radical. The present invention relates to a compound represented by the general formula (A); an acid- and radical-generating agent comprising the compound; and a method for generating an acid and a radical: wherein n pieces of R1 each independently represent an alkyl group, which may have a specific functional group in the chain, or in which a hydrogen atom may be substituted by a halogen atom; an alkoxy group, in which a hydrogen atom may be substituted by a halogen atom; an aryl group or an aryloxy group, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; or an arylalkyl group or an arylalkyloxy group, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; n pieces of R2 and R3 each independently represent a hydrogen atom, an alkyl group or an alkoxycarbonyl group; R4 to R7 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an alkoxycarbonyl group, a dialkylamino group or a nitro group; Y represents an oxygen atom, a sulfur atom, or a carbonyl group; n pieces of Z each independently represent a sulfonyl group or an alkoxyphosphoryl group; n represents 1 or 2.

  本发明的一个目的是提供一种对波长约为300至450纳米的活性能量射线具有高灵敏度的酸和自由基生成剂，能够发挥高酸生成性能和高自由基生成性能，并具有耐热性；以及一种生成酸和自由基的方法。本发明涉及一种由通式（A）表示的化合物；包括该化合物的酸和自由基生成剂；以及生成酸和自由基的方法：其中n个R1分别独立表示一种烷基基团，该烷基基团可能在链中具有特定的功能基团，或者氢原子可能被卤原子取代；一种烷氧基团，其中氢原子可能被卤原子取代；一种芳基或芳氧基，其中氢原子可能被卤原子，烷基或卤代烷基取代；或一种芳基烷基或芳基氧基，其中氢原子可能被卤原子，烷基或卤代烷基取代；n个R2和R3分别独立表示氢原子，烷基基团或烷氧羰基团；R4到R7分别独立表示氢原子，卤原子，烷基基团，烷氧基团，烯基基团，芳基，烷氧羰基团，二烷基氨基团或硝基；Y表示氧原子，硫原子或羰基；n个Z分别独立表示磺酰基或烷氧基磷酰基；n表示1或2。
• ACID- AND RADICAL-GENERATING AGENT AND METHOD FOR GENERATING ACID AND RADICAL
  申请人：WAKO PURE CHEMICAL INDUSTRIES, LTD.

  公开号：US20160342084A1

  公开（公告）日：2016-11-24

  It is a subject of the present invention to provide an acid- and radical-generating agent which has high sensitivity to an active energy ray having a wavelength of around 300 to 450 nm, and can exert both high acid-generating performance and high radical-generating performance, and has heat resistance; and a method for generating an acid and a radical. The present invention relates to a compound represented by the general formula (A); an acid- and radical-generating agent comprising the compound; and a method for generating an acid and a radical: wherein n pieces of R 1 each independently represent an alkyl group, which may have a specific functional group in the chain, or in which a hydrogen atom may be substituted by a halogen atom; an alkoxy group, in which a hydrogen atom may be substituted by a halogen atom; an aryl group or an aryloxy group, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; or an arylalkyl group or an arylalkyloxy group, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; n pieces of R 2 and R 3 each independently represent a hydrogen atom, an alkyl group or an alkoxycarbonyl group; R 4 to R 7 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an alkoxycarbonyl group, a dialkylamino group or a nitro group; Y represents an oxygen atom, a sulfur atom, or a carbonyl group; n pieces of Z each independently represent a sulfonyl group or an alkoxyphosphoryl group; n represents 1 or 2.
• US4379039A
  申请人：——

  公开号：US4379039A

  公开（公告）日：1983-04-05
• US9637565B2
  申请人：——

  公开号：US9637565B2

  公开（公告）日：2017-05-02
• Photochemistry of the 9-Hydroxyxanthenyl Radical in the Laser-Jet: Evidence for Photochemically Induced, Regioselective Radical Coupling
  作者：Waldemar Adam、Fumio Kita

  DOI：10.1021/ja00088a002

  日期：1994.5

  The conventional irradiation (low intensity) of xanthone in ethanol was observed to produce pinacol 3 by photoreductive coupling and 9-hydroxy-9-(1-hydroxyethyl)-9H-xanthene (4) by head-to-head cross-coupling between the resultant 9-hydroxyxanthenyl (2) and 1-hydroxyethyl radicals. Under laser-jet conditions (high intensity), in addition to products 3 and 4, 3-(1-hydroxyethyl)-9H-xanthen-9-one (5d) was obtained as the major head-to-tail cross-coupling product. The observed dependence of the product ratio of 4 and 5d on the irradiation intensity is rationalized in terms of the higher spin density in the aryl rings, particularly at the 3-position (para to the hydroxy-substituted carbon atom), of the electronically excited 9-hydroxyxanthenyl radical (2'). For the ground state radical 2, as expected, the majority of spin density resides at the hydroxy-substituted carbon atom and, thus, constitutes the precursor to the head-to-head cross-coupling product 4. The theoretical spin densities for the ground and excited state 9-hydroxyxanthenyl radicals 2, calculated by semiempirical MO methods (PM3), indicate that upon photoexcitation the electron density in the SOMO shifts from the hydroxy-substituted radical center (ground state) to the aromatic pi-system (first excited state) and is concentrated at the 1a- and 3-positions.