7-bromo-1-ethoxycarbonyl-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid | 1021304-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-bromo-1-ethoxycarbonyl-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
• CAS: 1021304-57-3
• 化学式: C₁₆H₁₇BrO₅
• 分子量: 369.212
• InChiKey: RQADRZVERLLCQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  6,6-dimethyl-7,8-dihydronaphtho[1,2-c]furan-1,3,9(6H)-trione 、 乙醇 在 copper(ll) bromide 作用下， 反应 19.0h， 以61%的产率得到7-bromo-1-ethoxycarbonyl-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Total Synthesis of (±)-Hyphodermins A and D

  摘要：

  An efficient formal synthesis of (+/-)-hyphodermins A and D, metabolites of Hyphoderma radula, has been completed in 12 and 11 steps, respectively. The tricyclic carbon skeleton of enone 6 was rapidly assembled from diester 11 via an alpha brominationn-elimination sequence followed by anhydride formation. Regioselective reduction of the lactone group of enone 6 with LiAlH(t-BUO)(3) gave lactol 15. Lactol 15 was converted in two steps to (+/-)-hyphodermin D, without the need for complex protection-deprotection strategies. Lactol 15 was converted in three steps to (+/-)-hyphodermin A, via the key step of epoxidation of an enone in the presence of a THP lactol. A combination of NMR and ab initio studies suggests that the structures of hyphodermin C and D should be interchanged.

  DOI：

  10.1021/jo800227p