7-bromo-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylic acid dimethyl ester | 1021304-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-bromo-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 7-bromo-5,5-dimethyl-8-oxo-6,7-dihydronaphthalene-1,2-dicarboxylate
• CAS: 1021304-62-0
• 化学式: C₁₆H₁₇BrO₅
• 分子量: 369.212
• InChiKey: XFEDBXFFZMRELQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-bromo-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylic acid dimethyl ester 在 三乙烯二胺 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 5,5-dimethyl-8-oxo-5,8-dihydronaphthalene-1,2-dicarboxylic acid dimethyl ester
  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
• 作为产物：
  描述：

  dimethyl 5,5-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylate 在 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以75%的产率得到7-bromo-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylic acid dimethyl ester
  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

文献信息

• Total Synthesis of (±)-Hyphodermins A and D
  作者：Wendy A. Loughlin、Ian D. Jenkins、Luke C. Henderson、Marc R. Campitelli、Peter C. Healy

  DOI：10.1021/jo800227p

  日期：2008.5.1

  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.