1-(3-hydroxybenzo[b]selenophen-2-yl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-hydroxybenzo[b]selenophen-2-yl)ethanone
• 英文别名: 2-acetyl-3-hydroxybenzo[b]selenophene；2-acetylbenzo[b]selenophen-3(2H)-one；1-(3-Hydroxy-1-benzoselenophen-2-yl)ethanone
• 化学式: C₁₀H₈O₂Se
• 分子量: 239.132
• InChiKey: QOFZEYSHCGQWCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxybenzo[b]selenophen-2-yl)ethanone 在 肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以92%的产率得到3-methylbenzo[b]selenopheno[2,3-d]pyrazole
  参考文献：
  名称：

  一种简单的合成方法，用于构建某些Ebselen类似物和苯并[b]硒烯衍生物：其抗氧化和细胞毒性评估

  摘要：

  2-（Chloroseleno）苯甲酰氯用作一个多功能结构单元为新颖依布硒（2-苯基-1,2-苯并异硒唑-3（2的合成ħ） -酮）类似物和苯并[ b ]硒吩-3（2 ħ）-一阶导数 进行了新合成化合物的抗氧化活性和细胞毒性评估。在所有合成的化合物中，1-（3-羟基苯并[ b ]硒代苯并-2-基）乙酮肟（9）是最有效的抗氧化剂，也是最具细胞毒性的化合物。

  DOI：

  10.1002/jhet.3199
• 作为产物：
  描述：

  苯甲酰氯,2-(氯硒代)- 以 丙酮 为溶剂， 反应 0.25h， 生成 1-(3-hydroxybenzo[b]selenophen-2-yl)ethanone
  参考文献：
  名称：

  Selenenylation–acylation of ketones with 2-chloroselenobenzoyl chloride. A novel route to benzo[b]selenophenes

  摘要：

  It has been found thar enolizable ketones and 1,3-diones react in neutral or basic medium with biselectrophiles such as 2-chloroselenobenzoyl chloride. The reaction takes place on the active alpha -methylene group. Selenenylation and subsequent acylation of the alpha -carbon atom take place and. depending on the ketone used, 3-hydroxybenzo[b]selenophenes or benzo[b]selenophen-3(2H)-ones are produced in moderate to high yields. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00839-5

文献信息

• 2-(Chloroseleno)benzoyl Chloride: A Tandem Reagent for Selenenylation-Acylation of C-H Acids
  作者：Krystian Kloc、Mariusz Osajda、Jacek Mlochowski

  DOI：10.1246/cl.2001.826

  日期：2001.8

  The 2-(chloroseleno)benzoyl chloride is a bifunctional electrophile able to react with C-H acids. The selenenylation and acylation of the active methylene group in the presence of triethylamine, lead to the ring closure. Based on this reaction 2-substituted benzo[b]selenophen-3(2H)-ones and 3-hydroxybenzo[b]selenophenes are produced in moderate to high yields.

  2-（氯硒代）苯甲酰氯是一种双功能亲电试剂，能够与 CH 酸反应。在三乙胺存在下，活性亚甲基的硒基化和酰化导致闭环。基于该反应，2-取代苯并[b]硒酚-3(2H)-酮和3-羟基苯并[b]硒酚以中等至高产率生产。
• Facile Method for Conversion of 2-(Chloroseleno)benzoyl Chloride into 2-Substituted 3-Hydroxybenzo[<i>b</i>]selenophenes
  作者：Rafał Lisiak、Jacek Młochowski

  DOI：10.1080/00397910902898627

  日期：2009.11.5

  Abstract The easily accessible 2-(chloroseleno)benzoyl chloride has broad application in the synthesis of benzizoselenazol-3(2H)-ones and benzo[b]selenophen-3(2H)-ones. Treatment of 2-acylbenzo[b]selenophen-3(2H)-ones with nitrogen nucleophiles such as hydrazines and hydroxylamine resulted in formation of 2-substituted 3-hydroxybenzo[b]selenophenes in 72–98% yield.

  摘要 易得的2-(氯硒代)苯甲酰氯在苯并硒唑-3(2H)-酮和苯并[b]硒酚-3(2H)-酮的合成中具有广泛的应用。用氮亲核试剂（如肼和羟胺）处理 2-酰基苯并[b]硒酚-3(2H)-酮，以 72-98% 的产率形成 2-取代的 3-羟基苯并 [b] 硒酚。
• WEBER R.; RENSON M., BULL. SOC. ROY. SCI. LIEGE, 1979, 48, NO 3-4, 146-151
  作者：WEBER R.、 RENSON M.

  DOI：——

  日期：——
• An Easy Synthetic Approach to Construct Some Ebselen Analogues and Benzo[<i>b</i>]selenophene Derivatives: Their Antioxidant and Cytotoxic Assessment
  作者：Mohamed Elsherbini、Wafaa S. Hamama、Hanafi H. Zoorob

  DOI：10.1002/jhet.3199

  日期：2018.7

  2‐(Chloroseleno)benzoyl chloride serves as a versatile building block for the synthesis of novel ebselen (2‐phenyl‐1,2‐benzisoselenazol‐3(2H)‐one) analogues and benzo[b]selenophen‐3(2H)‐one derivatives. The antioxidant activity and cytotoxic evaluation of the newly synthesized compounds were implemented. Among all the synthesized compounds, 1‐(3‐hydroxybenzo[b]selenophen‐2‐yl)ethanone oxime (9) was

  2-（Chloroseleno）苯甲酰氯用作一个多功能结构单元为新颖依布硒（2-苯基-1,2-苯并异硒唑-3（2的合成ħ） -酮）类似物和苯并[ b ]硒吩-3（2 ħ）-一阶导数 进行了新合成化合物的抗氧化活性和细胞毒性评估。在所有合成的化合物中，1-（3-羟基苯并[ b ]硒代苯并-2-基）乙酮肟（9）是最有效的抗氧化剂，也是最具细胞毒性的化合物。
• Selenenylation–acylation of ketones with 2-chloroselenobenzoyl chloride. A novel route to benzo[b]selenophenes
  作者：Krystian Kloc、Jacek Młochowski

  DOI：10.1016/s0040-4039(01)00839-5

  日期：2001.7

  It has been found thar enolizable ketones and 1,3-diones react in neutral or basic medium with biselectrophiles such as 2-chloroselenobenzoyl chloride. The reaction takes place on the active alpha -methylene group. Selenenylation and subsequent acylation of the alpha -carbon atom take place and. depending on the ketone used, 3-hydroxybenzo[b]selenophenes or benzo[b]selenophen-3(2H)-ones are produced in moderate to high yields. (C) 2001 Published by Elsevier Science Ltd.