2-Acetamido-6-bromobenzene-1,4-dione | 87013-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetamido-6-bromobenzene-1,4-dione
• 英文别名: 2-acetamido-6-bromo-1,4-benzoquinone；2-bromo-6-acetamido-1,4-benzoquinone；2-acetylamino-6-bromo-[1,4]benzoquinone；N-(5-Brom-3.6-dioxo-cyclohexadien-(1.4)-yl)-acetamid；2-Acetylamino-6-brom-[1,4]benzochinon；6-Brom-2-acetamino-benzochinon-(1.4)；N-(5-bromo-3,6-dioxocyclohexa-1,4-dien-1-yl)acetamide
• CAS: 87013-12-5
• 化学式: C₈H₆BrNO₃
• 分子量: 244.045
• InChiKey: HUHSSAYBQYUPJU-UHFFFAOYSA-N

物化性质

• 熔点：
  183 °C
• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Acetamido-6-bromobenzene-1,4-dione 在 溴 、 溶剂黄146 作用下， 生成 2,2,4,5-四溴环戊-4-烯-1,3-二酮
  参考文献：
  名称：

  Heller et al., Journal fur praktische Chemie (Leipzig 1954), 1931, vol. <2> 129, p. 211,229

  摘要：

  DOI：
• 作为产物：
  描述：

  2-acetamido-4,6-dibromophenol 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.17h， 以67%的产率得到2-Acetamido-6-bromobenzene-1,4-dione
  参考文献：
  名称：

  Synthesis of 6-bromo- and 6-chloro-2-acetamidobenzoquinone. A structure revision

  摘要：

  DOI：

  10.1021/jo00169a061

文献信息

• Diels-Alder reactions of N-silyloxy 1-azadienes
  作者：Mohammad Behforouz、Zhengxiang Gu、Lindsay S. Stelzer、Mohammad Ahmadian、Jalal Haddad、John A. Scherschel

  DOI：10.1016/s0040-4039(97)00326-2

  日期：1997.3

  xy)-1-aza-1,3-butadienes 1 and 2 are prepared by the reaction of O-(t-butyldimethylsilyloxy)hydroxylamine with methyl vinyl ketone and methacrolein, respectively. Azadienes 1 and 2 through sharing of oxygen nonbonding electrons are activated and thus their Diels-Alder reactions with a number of halobenzoquinones, napthoquinones and N-phenylmaleimide regiospecifically give low to good yields of various

  新型的1-（叔丁基二甲基甲硅烷氧基）-1-氮杂-1,3-丁二烯1和2是通过O-（叔丁基二甲基甲硅烷氧基）羟胺分别与甲基乙烯基酮和甲基丙烯醛反应制备的。通过共享氧非键电子的氮杂二烯1和2被激活，因此它们与许多卤代苯醌，萘醌和N-苯基马来酰亚胺的Diels-Alder反应区域特异性地给出了各种吡啶杂环的低至良好的收率。
• LAVENDAMYCIN ANALOGS, QUINOLINE-5,8-DIONES AND METHODS OF USING THEM
  申请人：Ball State University

  公开号：US20040248922A1

  公开（公告）日：2004-12-09

  The invention provides novel lavendamycin analogs having the following general formula: 1 and quinoline-5,8-diones having the following formula: 2 Methods of making and using and compositions containing these compounds are also disclosed.

  本发明提供了具有以下一般式的新型薰衣草霉素类似物：1，以及具有以下式子的喹啉-5,8-二酮：2。还公开了制备和使用这些化合物以及含有这些化合物的组合物的方法。
• Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones
  作者：Mohammad Behforouz、Wen Cai、Farahnaz Mohammadi、Mark G. Stocksdale、Zhengxiang Gu、Mohammad Ahmadian、Darric E. Baty、Michele R. Etling、Charmaine H. Al-Anzi、Tyson M. Swiftney

  DOI：10.1016/j.bmc.2006.09.039

  日期：2007.1.1

  A series of 7-N-acyllavendamycins with zero, one or two substituents at the C-2', C-3', and C-11' were synthesized through short and efficient methods. Pictet-Spengler condensation of 7-N-acylamino-2-formylquinoline-5,8-diones with tryptamine or tryptophans produced the desired lavendamycins. Screening data on a panel of three ras oncogene-transformed cell lines and the non-transformed parent cell line showed that a significant number of these analogues are potent antitumor agents and appear to be particularly active against K-ras transformed cells. Compared with the corresponding quinolinediones, these novel lavendamycins are much more inhibitory toward the transformed cells indicating that the P-carboline moiety of the lavendamycin analogues plays an important role in its potency and selective toxicity. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of the rifamycin chromophore
  作者：T.Ross Kelly、Mohammad Behforouz、Antonio Echavarren、Jacob Vaya

  DOI：10.1016/s0040-4039(00)81917-6

  日期：1983.1
• A highly concise synthesis of lavendamycin methyl ester
  作者：Mohammad Behforouz、Zhengxiang Gu、Wen Cai、Mark A. Horn、Mohammad Ahmadian

  DOI：10.1021/jo00077a032

  日期：1993.12

  Lavendamycin methyl ester (2), an antitumor antibiotic, was synthesized by a practical and short route in an excellent overall yield of 33% from known starting materials. Pictet-Spengler condensation of 7-acetamido-2-formylquinoline-5,8-dione (4) with the methyl ester of (2RS,3SR)-beta-methyltryptophan (5) followed by hydrolysis afforded 2. Aldehyde 4 was prepared by the oxidation of 7-acetamido-2-methylquinoline-5,8-dione (9). Dione 9 was obtained via the Diels-Alder condensation of the novel 1-[(tert-butyldimethylsilyl)oxy]-2-methyl-1-aza-1,3-butadiene (7) with 2-acetamido-6-bromobenzene-1,4-dione (8).