1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-ene-2,3-diol | 819070-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-ene-2,3-diol
• CAS: 819070-96-7
• 化学式: C₉H₁₀Br₄O₄
• 分子量: 501.792
• InChiKey: YHTIVQOPOBOCBM-SOSBWXJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-ene-2,3-diol 在 吡啶 、 chromium(VI) oxide 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 115.0h， 生成 3-(benzyloxy)-1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-one
  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：

  1,2,3,4-tetrabromo-5,5-dimethoxycyclopenta-1,3-diene 在 水 、 potassium carbonate 、 对苯二酚 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 84.0h， 生成 1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-ene-2,3-diol
  参考文献：
  名称：

  A short and stereoselective synthesis of functionalized pentenomycin derivatives

  摘要：

  A short and stercoselective synthesis of 2-hydroxymethyl-4-deoxypentenomycin and 2-hydoxymethylpentenomycin derivatives is accomplished in five and seven steps starting from tetrabromonorbornyl derivatives in overall yields of 41% and 38%, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.065