2-溴-3,5-二甲氧基-6-甲基环己-2,5-二烯-1,4-二酮 | 383179-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-3,5-二甲氧基-6-甲基环己-2,5-二烯-1,4-二酮
• 英文名称: 2-bromo-3,5-dimethoxy-6-methyl-p-benzoquinone
• 英文别名: 2-bromo-3,5-dimethoxy-6-methyl-[1,4]benzoquinone；2-Brom-3,5-dimethoxy-6-methyl-[1,4]benzochinon；2,5-Cyclohexadiene-1,4-dione, 2-bromo-3,5-dimethoxy-6-methyl-；2-bromo-3,5-dimethoxy-6-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 383179-83-7
• 化学式: C₉H₉BrO₄
• 分子量: 261.072
• InChiKey: VIXVABNGNPRFBC-UHFFFAOYSA-N

物化性质

• 沸点：
  351.4±42.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-3,5-二甲氧基-6-甲基环己-2,5-二烯-1,4-二酮 、 1-(1-phenylethyl)-2-(tributylstannylmethylene)pirrolidine 以 四氢呋喃 为溶剂， 以38%的产率得到2-Bromo-5-methoxy-6-methyl-3-[1-(1-phenyl-ethyl)-pyrrolidin-(2E)-ylidenemethyl]-[1,4]benzoquinone
  参考文献：
  名称：

  Use of the Vicinal Element Effect for Regiochemical Control of Quinone Substitutions and Its Implication for Convergent Mitomycin Construction

  摘要：

  [GRAPHICS]Nucleophilic substitution reactions of 2-methoxy-3-alkyl-p-benzoquinones are described as they relate to the construction of the mitomycin backbone. Normally controlled by activating groups attached to the olefin, the observed regioselection in these cases is determined by the deactivating substituent. Approximation of carbonyl activating ability would not have predicted the behavior of two systems investigated in which the poorer of two leaving groups is substituted in each case.

  DOI：

  10.1021/ol016625z
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯仿 、 溴 作用下， 生成 2-溴-3,5-二甲氧基-6-甲基环己-2,5-二烯-1,4-二酮
  参考文献：
  名称：

  Analysis of Moisture Findings in the Interior Spaces of Finnish Housing Stock

  摘要：

  A grading system was developed to rate the moisture damage profile of dwellings and to study the relationship between moisture-induced indoor air problems and occupant health. A total of 630 randomly selected houses and apartments, built between 1950 and 1989, were visually inspected. Moisture observations were standardized into three damage levels. Thus, a system to classify the homes into three grades was devised. The two grades of homes associated with the highest levels of damage were graded as index homes.Overall, 51% of the sample had some kind of moisture fault in them and one in every three homes (33%) was classified as an index home. The mean number of damage incidents in the index dwellings varied from 1.4 to 2.6. The mean number of damage incidents in the reference homes was 0.28. Prevalence of index dwellings was significantly higher (p < 0.01) in houses (38%) than in apartments (26%). There was no major difference in the prevalence of index buildings in houses built in any particular decade (30-35%). Moisture was observed in 28% of bathrooms, in 10% of kitchens, and in 17% of other spaces. Indoor relative humidity (RH) levels were low in most homes.

  DOI：

  10.1080/10473289.2001.10464245

文献信息

• Stereoselective synthesis of complex polycyclic aziridines: use of the Brønsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency
  作者：Jayasree M. Srinivasan、Priya A. Mathew、Amie L. Williams、John C. Huffman、Jeffrey N. Johnston

  DOI：10.1039/c0cc05734g

  日期：——

  A concise synthesis of a highly functionalized intermediate lacking only C10 of the mitomycin backbone is described. The key to this development is the Brønsted acid-catalyzed aza-Darzens reaction used to forge the cis-aziridine. Additionally an oxidative ketalization fortuitously occurs during the quinone–enamine coupling step, leading to an orthogonally protected hydroquinone.

  一种高度功能化的中间体，仅缺少丝裂霉素骨架中的C10，其简明合成方法被描述。这一进展的关键在于使用布朗斯特酸催化的aza-达琴反应构建顺式氮杂环丙烷。此外，在醌与烯胺偶联步骤中偶然发生的氧化缩酮化反应，导致生成了一种正交保护的氢醌。
• Synthesis of an Advanced Intermediate en Route to the Mitomycin Natural Products
  作者：Amie L. Williams、Jayasree M. Srinivasan、Jeffrey N. Johnston

  DOI：10.1021/ol0624676

  日期：2006.12.1

  [Structure: see text] An advanced intermediate in our planned synthesis of mitomycin C has been acquired in nine steps from tert-butyl glyoxylate. The aziridinyl pyrrolidine and quinone subunits are coupled regioselectively to arrive at an enamine that is prepared for C10 homologation.

  [结构：见正文]我们从计划的乙醛酸叔丁酯的九步中获得了我们计划的丝裂霉素C合成中的高级中间体。叠氮基吡啶基吡咯烷和醌亚基区域选择性地偶联以获得烯胺，该烯胺准备用于C10同源化。