3-bromo-2-hydroxycyclopent-2-en-1-one | 3019-83-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 3-bromo-2-hydroxycyclopent-2-en-1-one
• 英文别名: 3-bromo-2-hydroxycyclopent-2-enone；3-bromo-2-hydroxy-2-cyclopenten-1-one；3-Brom-2-hydroxy-cyclopent-2-en-1-on；3-Brom-2-hydroxy-2-cyclopenten-1-on；3-Brom-2-hydroxycyclopent-2-en-1-on；3-Brom-2-hydroxycyclopenten-2-on
• CAS: 3019-83-8
• 化学式: C₅H₅BrO₂
• 分子量: 176.997
• InChiKey: PXQWRIXZCNCEIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3-bromo-2-hydroxycyclopent-2-en-1-one 在 sodium methylate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 2,3-dimethoxy-2-cyclopent-1-one
  参考文献：
  名称：

  Total Synthesis of Dimethyl Glolosiphone Aviaα-Carbonyl Radical Spiro-Cyclization

  摘要：

  AbstractA general approach toward spiro[4.4]nonane structure based on the α‐carbonyl radical cyclization has been developed. Efficient total synthesis of dimethyl gloiosiphone A (2) was achieved. Thus, alkylation of the anion of dimethylhydrazone of cyclopentanone with 5‐iodopent‐1‐yne followed by hydrolysis gave ketone 4. Iodination of 4 via its TMS‐enol ether yielded iodo ketone 7. Radical spiro‐cyclization of 7 gave spiro ketone 10. Iodination of 10 afford iodo spiro ketone 23. Oxidation and iodination of 23 gave compound 24. Methylation of 24 furnished methoxy iodo enone 25. Substitution of iodide in 25 with methoxide produced dimethoxy enone 26. Allylic oxidation of 26 gave diketone 27. Treatment of 27 with OsO4 and N‐methylmorpholine N‐oxide gave dihydroxy ketone 28. Methylation of the primary alcohol group in 28 afforded dimethyl gloiosiphone A (2).

  DOI：

  10.1002/jccs.199900064
• 作为产物：
  描述：

  环辛烷-1,2-二酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 以89%的产率得到3-bromo-2-hydroxycyclopent-2-en-1-one
  参考文献：
  名称：

  3-溴1,2-二酮的Sonogashira交叉偶联：进入3-炔基1,2-二酮的途径

  摘要：

  开发了一种新的合成3-环炔基取代的1,2-二酮烯醇的通用方法。环状3-溴-环戊烷和3-溴-环己烷-1,2-二酮的甲硅烷基烯醇酸酯与各种取代乙炔的Sonogashira交叉偶联提供了高收率的环状3-炔基-1,2-二酮的烯醇到93％）。起始的3-溴-1,2-二酮很容易通过用NBS直接溴化1,2-二酮来获得。

  DOI：

  10.1016/j.tet.2014.06.037

文献信息

• Synthesis of Cyclic 3-Aryl-Substituted 1,2-Dicarbonyl Compounds via Suzuki Cross-Coupling Reactions
  作者：Margus Lopp、Eleana Lopušanskaja、Anne Paju、Ivar Järving

  DOI：10.1055/s-0036-1591543

  日期：2018.5

  the synthesis of cyclic 3-aryl- and heteroaryl-substituted 1,2-dicarbonyl compounds with different ring sizes by using a Suzuki cross-coupling reaction between 3-halo-1,2-dicarbonyl compounds and arylboronic acids is developed. The 3-halo-1,2-dicarbonyl substrates are easily available from 1,2-dicarbonyl compounds. The method is versatile, affording good to high yields of the target compounds. A method

  摘要 开发了一种通过使用3-卤代1,2-二羰基化合物与芳基硼酸之间的铃木交叉偶联反应合成具有不同环尺寸的环状3-芳基-和杂芳基取代的1,2-二羰基化合物的方法。3-卤代1,2-二羰基底物很容易从1,2-二羰基化合物获得。该方法是通用的，提供了良好至高产率的目标化合物。 开发了一种通过使用3-卤代1,2-二羰基化合物与芳基硼酸之间的铃木交叉偶联反应合成具有不同环尺寸的环状3-芳基-和杂芳基取代的1,2-二羰基化合物的方法。3-卤代1,2-二羰基底物很容易从1,2-二羰基化合物获得。该方法是通用的，提供了良好至高产率的目标化合物。
• MAPK/ERK KINASE INHIBITORS
  申请人：Adams Mark E.

  公开号：US20080312307A1

  公开（公告）日：2008-12-18

  Compounds are provided for inhibition of MEK that comprise: wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.

  提供了一些用于抑制MEK的化合物，其中变量的定义如下。此外，还提供了包含这些化合物的药物组合物、工具箱和制造物品；用于制备这些化合物的方法和中间体；以及使用这些化合物的方法。
• WO2008/148034
  申请人：——

  公开号：——

  公开（公告）日：——
• Radical Scavenging Activity of Ascorbic Acid Analogs Containing a Carbonyl Conjugated Ene-Diol Structure
  作者：Masataka Mochizuki、Shogo Nomura、Keiko Inami

  DOI：10.3987/com-15-13366

  日期：——

  Small molecule antioxidants such as ascorbic acid (AscH(2)) prevent the oxidative damage of biological molecules by scavenging reactive oxygen species. A carbonyl-conjugated ene-diol structure is essential for the antioxidant activity of AscH(2). As such, we synthesized novel AscH(2) analogs containing a carbonyl conjugated ene-diol structure and evaluated their radical scavenging activities. When the 1,2-dihydroxyethyl group was removed, radical scavenging activity equal to AscH(2) was observed. Analogs containing an endocyclic nitrogen atom instead of a ring oxygen displayed higher radical scavenging activities than AscH(2). Therefore, the electron donating effect of the carbonyl conjugated ene-diol structure greatly increased the radical scavenging activity of AscH(2) analogs.
• 3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: an approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids
  作者：Anne Paju、Diana Kostomarova、Katharina Matkevitš、Marit Laos、Tõnis Pehk、Tõnis Kanger、Margus Lopp

  DOI：10.1016/j.tet.2015.10.014

  日期：2015.12

  Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methylalkoxycarbonyl- and 3(2-Boc-aminoethyl)-alkoxycarbonyl-1,2-cyclopentanediones homocitric and lycoperdic acid precursors. Homocitric and lycoperdic acids were synthesized using asymmetric oxidation with the Ti(OiPr)(4)/tartaric ester/tBuOOH complex in two steps from the obtained precursors. (C) 2015 Elsevier Ltd. All rights reserved.

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