2-(2-Bromo-benzyl)-[1,4]naphthoquinone | 379693-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-Bromo-benzyl)-[1,4]naphthoquinone
• 英文别名: 2-[(2-Bromophenyl)methyl]naphthalene-1,4-dione
• CAS: 379693-76-2
• 化学式: C₁₇H₁₁BrO₂
• 分子量: 327.177
• InChiKey: CJPQXJSNZCJHOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Bromo-benzyl)-[1,4]naphthoquinone 在 sodium dithionite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 生成 C₁₇H₁₃BrO₂
  参考文献：
  名称：

  A novel approach to the synthesis of benzo[b]fluoren-11-ones

  摘要：

  A novel intramolecular palladium-mediated arylation approach to benzo[b]fluoren-11-ones has been investigated. This approach involves the novel oxidation of the key starting 2-(2'-bromobenzyl)naphthols to 2-(2'-bromobenzyl)-1,4-naphthoquinones,followed by protection of the quitione moiety of the latter compounds and the final Pd-promoted bi-arylic cyclization of the resulting 2-(2'-bromobenzyl)-1,4-dimethoxynaphthalenes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.112
• 作为产物：
  描述：

  2-(2-bromobenzyl)-1-naphthol 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.5h， 以80%的产率得到2-(2-Bromo-benzyl)-[1,4]naphthoquinone
  参考文献：
  名称：

  A novel approach to the synthesis of benzo[b]fluoren-11-ones

  摘要：

  A novel intramolecular palladium-mediated arylation approach to benzo[b]fluoren-11-ones has been investigated. This approach involves the novel oxidation of the key starting 2-(2'-bromobenzyl)naphthols to 2-(2'-bromobenzyl)-1,4-naphthoquinones,followed by protection of the quitione moiety of the latter compounds and the final Pd-promoted bi-arylic cyclization of the resulting 2-(2'-bromobenzyl)-1,4-dimethoxynaphthalenes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.112

文献信息

• Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds
  作者：An-I Tsai、Yi-Lung Wu、Che-Ping Chuang

  DOI：10.1016/s0040-4020(01)00754-2

  日期：2001.9

  Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds are described. Electrophilic carbon-centered radicals produced by the manganese(III) acetate or cerium(IV) ammonium nitrate oxidation of β-dicarbonyl compounds undergo efficient addition to a C–C double bond of quinone ring. This free radical reaction provides a novel method for the synthesis of naphthacene-5

  描述了2-苄基-1,4-萘醌与β-二羰基化合物之间的氧化自由基反应。β-二羰基化合物的乙酸锰（III）或硝酸铈（IV）硝酸铵氧化产生的亲电子碳中心自由基经过有效地加成至醌环的C-C双键。该自由基反应提供了合成萘并5，12-二酮的新方法。
• Oxidative Free Radical Cyclization of 2-(Ethoxycarbonylmethyl)-1,4-naphthoquinone Derivatives
  作者：Che-Ping Chuang、Hui-Li Chen、Chien-Yu Lin、Yu-Chih Cheng、An-I Tsai

  DOI：10.1055/s-2005-861850

  日期：——

  A manganese(III)-mediated oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4-naphthoquinone derivatives is described. These starting 2-(ethoxycarbonylmethyl)-1,4-naphthoquinones can be synthesized effectively from the reaction of corresponding 1,4-naphthoquinones with ethyl nitroacetate. With 2-benzyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, naphthacene-5,12-diones were produced

  描述了锰 (III) 介导的 2-(乙氧基羰基甲基)-1,4-萘醌衍生物的氧化自由基环化。这些起始的2-(乙氧基羰基甲基)-1,4-萘醌可以通过相应的1,4-萘醌与硝基乙酸乙酯的反应有效合成。以2-苄基-3-(乙氧基羰基甲基)-1,4-萘醌为原料，高效生产并高选择性的5,12-并四苯。使用乙基 2-benzoyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones，除了预期的 6-hydroxynaphthacene-5,12-diones，新型萘并[2,3-c]furan-4,9-diones也形成了主打产品。