1,3,5-tribromo-2-methoxy-4-(2-methoxyvinyl)benzene | 1359715-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3,5-tribromo-2-methoxy-4-(2-methoxyvinyl)benzene
• CAS: 1359715-24-4
• 化学式: C₁₀H₉Br₃O₂
• 分子量: 400.892
• InChiKey: IAPBRCBCLLJWPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,3,5-tribromo-2-methoxy-4-(2-methoxyvinyl)benzene 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以4.53 g的产率得到2-(2,4,6-tribromo-3-methoxyphenyl)acetaldehyde
  参考文献：
  名称：

  Synthesis of Reported and Revised Structures of Amathamide D and Synthesis of Convolutamine F, H and Lutamide A, C

  摘要：

  Total synthesis of the published structure of amathamide D is described. Methyl 2,3,4-tribromo-5-hydroxybenzoate was selected as starting compound because it is readily accessible via acid-mediated Grob fragmentation- aromatization reaction of 1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-one. The aforementioned ester was transformed into the reported structure of amathamide D through methylation of a hydroxyl group and conversion of the ester moiety to a beta-aminoethyl side chain. The NMR data of the synthetic compound did not conform to the reported natural product structure possessing contiguously positioned beta-aminoethyl side chain, a set of three adjacent bromines, and a methyl ether linkage on the phenyl ring. This prompted us to redefine the natural product structure by synthesizing a product whose spectral data exactly matched with the reported data of amathamide D. The convolutamine H, with completely substituted phenyl ring adorned with an extra methyl ether functional group, has also been synthesized by application of Grob fragmentation-aromatization strategy to 3-(benzyloxy)-1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-one. This approach furnished directly methyl 2,3,4-tribromo-5,6-dimethoxybenzoate, which was converted straightforwardly into convolutamine H. Further, synthesis of convolutamine F and lutamide A and C is also described.

  DOI：

  10.1021/jo3000173
• 作为产物：
  描述：

  2,4,6-tribromo-3-methoxybenzaldehyde 、 (methoxymethyl)triphenylphosphonium chloride 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.83h， 生成 1,3,5-tribromo-2-methoxy-4-(2-methoxyvinyl)benzene
  参考文献：
  名称：

  Synthesis of Reported and Revised Structures of Amathamide D and Synthesis of Convolutamine F, H and Lutamide A, C

  摘要：

  Total synthesis of the published structure of amathamide D is described. Methyl 2,3,4-tribromo-5-hydroxybenzoate was selected as starting compound because it is readily accessible via acid-mediated Grob fragmentation- aromatization reaction of 1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-one. The aforementioned ester was transformed into the reported structure of amathamide D through methylation of a hydroxyl group and conversion of the ester moiety to a beta-aminoethyl side chain. The NMR data of the synthetic compound did not conform to the reported natural product structure possessing contiguously positioned beta-aminoethyl side chain, a set of three adjacent bromines, and a methyl ether linkage on the phenyl ring. This prompted us to redefine the natural product structure by synthesizing a product whose spectral data exactly matched with the reported data of amathamide D. The convolutamine H, with completely substituted phenyl ring adorned with an extra methyl ether functional group, has also been synthesized by application of Grob fragmentation-aromatization strategy to 3-(benzyloxy)-1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-one. This approach furnished directly methyl 2,3,4-tribromo-5,6-dimethoxybenzoate, which was converted straightforwardly into convolutamine H. Further, synthesis of convolutamine F and lutamide A and C is also described.

  DOI：

  10.1021/jo3000173

文献信息

• Acid mediated synthesis of thiazolines, thiazoles and enamide derivatives from methyl enol ethers: Application towards synthesis of wilsoniamine B
  作者：Tapan Kumar Jena、Faiz Ahmed Khan

  DOI：10.1016/j.tetlet.2020.151675

  日期：2020.3

  metal-free synthesis of thiazolines, dihydrothiazole and enureas or thioureas from methyl enol ether with urea or thiourea derivatives in the presence of TFA (trifluoroacetic acid) are reported here. This synthetic protocol involves the formation of two bonds, C-N as well as C-S, in one step for the synthesis of thiazoline derivatives, dihydrothiazoles and a direct C-N bond for the synthesis of enamides

  本文报道了在TFA（三氟乙酸）存在下，由甲基烯醇醚与尿素或硫脲衍生物有效地无金属合成噻唑啉，二氢噻唑和脲或硫脲。该合成方案涉及在一步合成噻唑啉衍生物，二氢噻唑和直接CN键的两个步骤，即CN和CS的形成，从而以良好或优异的产率合成烯酰胺。此外，该方法用于合成wilsoniamine B生物碱。