5,6-dibromo-4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide | 623932-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,6-dibromo-4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide
• 英文别名: Bcklwnvuxridkk-uhfffaoysa-；5,6-dibromo-4,7-dimethoxy-1,3-dihydro-2-benzothiophene 2,2-dioxide
• CAS: 623932-74-1
• 化学式: C₁₀H₁₀Br₂O₄S
• 分子量: 386.061
• InChiKey: BCKLWNVUXRIDKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-formyl-4-oxoquinoline-1(4H)-carboxylate 、 5,6-dibromo-4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide 以 三氯苯 为溶剂， 反应 9.0h， 以81%的产率得到ethyl (5aR,11aS)-8,9-dibromo-7,10-dimethoxy-12-oxo-5a,6,11,11a-tetrahydrobenzo[b]acridine-5-carboxylate
  参考文献：
  名称：

  A New Synthesis of Benzo[b]acridones

  摘要：

  本研究描述了合成新苯并[b]吖啶酮的新颖而高效的路线。该方法涉及 N-取代-4-喹啉酮-3-甲醛与邻苯醌二甲烷的 Diels-Alder 反应，通过环加成反应和原位变形反应生成苯并[b]-1,6,6a,12a-四氢吖啶酮。使用一定量的碘催化这些四氢吖啶酮在二甲基亚砜中的氧化反应，可以得到新的苯并[b]吖啶酮衍生物。实验证明，只有当存在一个电子撤回的 N 保护基团时，环化反应才会有效。

  DOI：

  10.1055/s-0028-1087372
• 作为产物：
  描述：

  2,3-二甲基氢醌 在 aluminum oxide 、 Oxone 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 溴 、 potassium carbonate 、 sodium sulfite 作用下， 以 四氯化碳 、 乙醇 、 氯仿 、 丙酮 为溶剂， 反应 49.0h， 生成 5,6-dibromo-4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide
  参考文献：
  名称：

  New Benzo[ b ]xanthones from Diels-Alder Reactions of Chromone-3-carboxaldehydes with ortho -Benzoquinodimethanes

  摘要：

  New benzo[b]xanthone derivatives, having substituents in the A and D rings, were prepared from cycloaddition reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethanes, generated in situ from 1,3-dihydrobenzo[c]thiophene 2,2-dioxide, followed by oxidation of the obtained diastereomeric adducts. The structure of all compounds was fully established by 1D and 2D NMR, MS, and elemental analysis. The stereochemistry of the obtained diastereomeric cycloadducts was established by NOESY experiments.

  DOI：

  10.1007/s00706-002-0567-7

文献信息

• New Benzo[ b ]xanthones from Diels-Alder Reactions of Chromone-3-carboxaldehydes with ortho -Benzoquinodimethanes
  作者：Angela Sandulache、Artur M. S. Silva、Jos� A. S. Cavaleiro

  DOI：10.1007/s00706-002-0567-7

  日期：2003.3.1

  New benzo[b]xanthone derivatives, having substituents in the A and D rings, were prepared from cycloaddition reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethanes, generated in situ from 1,3-dihydrobenzo[c]thiophene 2,2-dioxide, followed by oxidation of the obtained diastereomeric adducts. The structure of all compounds was fully established by 1D and 2D NMR, MS, and elemental analysis. The stereochemistry of the obtained diastereomeric cycloadducts was established by NOESY experiments.
• A New Synthesis of Benzo[<i>b</i>]acridones
  作者：Artur Silva、Raquel Seixas、Diana Pinto、José Cavaleiro

  DOI：10.1055/s-0028-1087372

  日期：——

  A novel and efficient route for the synthesis of new benzo[b]acridones has been described. It involves the Diels-Alder reaction of N-substituted-4-quinolone-3-carbaldehyde with ortho-benzoquinodimethanes giving benzo[b]-1,6,6a,12a-tetrahydroacridones, which are the result of a cycloaddition reaction followed by an in situ deformylation. The oxidation of these tetrahydroacridones in dimethyl sulfoxide using a catalytic amount of iodine gives the new benzo[b]acridone derivatives. It was demonstrated that the ­cycloaddition reaction is only efficient if an electron-withdrawing N-protecting group is present.

  本研究描述了合成新苯并[b]吖啶酮的新颖而高效的路线。该方法涉及 N-取代-4-喹啉酮-3-甲醛与邻苯醌二甲烷的 Diels-Alder 反应，通过环加成反应和原位变形反应生成苯并[b]-1,6,6a,12a-四氢吖啶酮。使用一定量的碘催化这些四氢吖啶酮在二甲基亚砜中的氧化反应，可以得到新的苯并[b]吖啶酮衍生物。实验证明，只有当存在一个电子撤回的 N 保护基团时，环化反应才会有效。

表征谱图