(3Z,5E,)-octa-3,5-diene-2,7-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3Z,5E,)-octa-3,5-diene-2,7-dione
• 英文别名: (3E,5Z)-3,5-octadien-2,7-dione；(3Z,5E)-octa-3,5-diene-2,7-dione
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: BCKGLINGXIXQPD-CIIODKQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,7-二甲基氧杂卓 在 ammonium cerium (IV) nitrate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (3Z,5E,)-octa-3,5-diene-2,7-dione
  参考文献：
  名称：

  Modeling the formation and reactions of benzene metabolites

  摘要：

  One or more of the muconaldehyde isomers is a putative product of benzene metabolism. As muconaldehydes are highly reactive dienals and potentially mutagenic they might be relevant to the carcinogenicity of benzene. Muconaldehydes may be derived through the action of a cytochrome P450 monooxygenase on benzene oxide-oxepin, which are established metabolites of benzene. Oxidation of benzene oxide-oxepin either by the one-electron oxidant cerium(IV) ammonium nitrate (CAN) or by iron(III) tris(1,10-phenanthroline) hexafluorophosphate in acetone at -78 degrees C or acetonitrile at -40 degrees C gave (E,Z)-muconaldehyde, which was a single diastereoisomer according to analysis by H-1 NMR spectroscopy. Reaction of toluene-1,2-oxide/2-methyloxepin with CAN gave (2E,4Z)-6-oxo-hepta-2,4-dienal. Similarly, the action of CAN on 1,6-dimethylbenzene oxide-2,7-dimethyloxepin gave (3Z,5E)-octa-3,5-diene-2,7-dione. In vivo, benzene oxide-oxepin could suffer one-electron oxidation by cytochrome P450 mono-oxygenase giving (E,Z)-muconaldehyde. The observations presented may be relevant to the toxicology of benzene oxide-oxepin and other arene oxide-oxepins as we have previously shown that (E,Z)-muconaldehyde, analogously to (Z,Z)-muconaldehyde, affords pyrrole adducts with the exocyclic amino groups of the DNA bases adenine and guanine. Independent of their possible toxicological significance, the experiments described provide preparatively useful routes to (E,Z)-muconaldehyde and its congeners. Methods are also described for the trapping and analysis of reactive benzene metabolites, e.g. using the Diels-Alder reaction with the dienophile 4-phenyl-1,2,4-triazoline-3,5-dione to trap arene oxides and with the diene 1,3-diphenylisobenzofuran to trap enals. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2010.01.001

文献信息

• PREPARATION OF TRANS,TRANS MUCONIC ACID AND TRANS,TRANS MUCONATES
  申请人：Frost John W.

  公开号：US20100314243A1

  公开（公告）日：2010-12-16

  The present invention relates to the isomerization of cis,cis and/or cis,trans muconic acid or esters thereof to trans,trans muconic acid or esters thereof and to the esterification of such muconic acids.

  本发明涉及将顺式、顺式和/或顺式、反式黏康酸或其酯异构化为反式、反式黏康酸或其酯，以及这些黏康酸的酯化过程。
• CYCLOHEXANE 1,4 CARBOXYLATES
  申请人：Frost John W.

  公开号：US20110288310A1

  公开（公告）日：2011-11-24

  The present invention relates to cyclohexanes having carboxylate derivatives at the 1 and 4, and optionally the 2, position. The invention also relates to processes for preparing such compounds wherein a portion of the starting materials utililzed is derived from renewable resources.

  本发明涉及在1和4位以及可选的2位具有羧酸酯衍生物的环己烷。本发明还涉及制备这种化合物的方法，其中所使用的起始材料的一部分来源于可再生资源。
• CYCLOHEXENE 1,4 -CARBOXYLATES
  申请人：Frost John W.

  公开号：US20110282078A1

  公开（公告）日：2011-11-17

  The present invention relates to cyclohexenes having carboxylate derivatives at the 1 and 4, and optionally the 2, position. The invention also relates to processes for preparing such compounds wherein a portion of the starting materials utilized is derived from renewable resources.

  本发明涉及在1和4位以及可选的2位具有羧酸酯衍生物的环己烯。本发明还涉及制备这种化合物的过程，其中所使用的起始材料的一部分是来自可再生资源的。
• BIOBASED POLYESTERS
  申请人：Frost John W.

  公开号：US20110288263A1

  公开（公告）日：2011-11-24

  The present invention relates to polyesters prepared from benzene, cyclohexene and cyclohexane compounds having carboxylic acid groups at the 1 and 4, and optionally the 2, positions, such as terephthalic acid or dimethyl terephthalates, and alkylene glycols, such ethylene glycol or 1,4-butane diol. The invention also relates to processes for preparing such polyesters. The invention also relates to such polyesters derived from starting materials derived from renewable resources.

  本发明涉及由苯、环己烯和环己烷化合物制备的聚酯，其在1和4位置，以及可选的2位置具有羧酸基团，例如对苯二甲酸或二甲基对苯二甲酸酯，以及乙二醇或1,4-丁二醇等碳链二醇。该发明还涉及制备此类聚酯的方法。该发明还涉及从可再生资源衍生的起始材料制备的这种聚酯。
• NOVEL TEREPHTHALIC AND TRIMELLITIC BASED ACIDS AND CARBOXYLATE DERIVATIVES THEREOF
  申请人：Frost John W.

  公开号：US20110288311A1

  公开（公告）日：2011-11-24

  The present invention relates to novel substituted and unsubstituted terephthalic acid and carboxylate derivatives and products prepared therefrom having a significant renewable content. The invention also relates to processes for preparing substituted and unsubstituted terephthalic and carboxylate derivatives thereof wherein a portion of the starting materials utilized is derived from renewable resources. The invention also relates to novel cyclohexene based intermediates prepared in these processes and to conversion of these intermediates to substituted and unsubstituted cyclohexane-1,4-dicarboxylates and carboxylate derivatives thereof and novel forms of the resulting products having renewable content. The invention also relates to products prepared from substituted and unsubstituted terephthalic acid and carboxylate derivatives thereof derived from starting materials derived from renewable resources.

  本发明涉及新型的取代和未取代的苯二甲酸和羧酸衍生物及其制备的产品，其具有显著的可再生含量。本发明还涉及制备取代和未取代的苯二甲酸和羧酸衍生物的过程，其中所使用的起始材料的一部分来源于可再生资源。本发明还涉及在这些过程中制备的新型环己烯基中间体，以及将这些中间体转化为取代和未取代的环己烷-1,4-二羧酸酯及其羧酸衍生物和具有可再生含量的新型形式的所得产品。本发明还涉及从可再生资源衍生的起始材料制备的取代和未取代的苯二甲酸和羧酸衍生物的产品。