6-bromo-3,4-dihydro-2-hydroxy-1(2H)-naphthalenone | 213249-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-bromo-3,4-dihydro-2-hydroxy-1(2H)-naphthalenone
• 英文别名: 6-bromo-2-hydroxy-3,4-dihydronaphthalen-1(2H)-one；6-bromo-2-hydroxy-3,4-dihydro-1(2H)-naphthalenone；6-bromo-2-hydroxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 213249-31-1
• 化学式: C₁₀H₉BrO₂
• 分子量: 241.084
• InChiKey: CTUWDHRJTDLLHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-3,4-dihydro-2-hydroxy-1(2H)-naphthalenone 在 4-二甲氨基吡啶 、 indium 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 34.0h， 生成 (3aS,9bS)-9b-Allyl-7-bromo-3a,4,5,9b-tetrahydro-naphtho[1,2-d][1,3]dioxol-2-one
  参考文献：
  名称：

  Allylindation of 6-Substituted 2-Hydroxy-1-tetralones in Aqueous and Organic Media. Stereochemistry and Competition Studies

  摘要：

  A systematic investigation of the stereoselectivity associated with coupling reactions involving the allylindium reagent-and 6-substituted 2-hydroxy-1-tetralones is presented. In each instance, the allylations were carried out in water, 50% aqueous THF, and dry THF. The extent of 1,2-induction was found to be highest-in THF-H2O (1:1) and to favor the trans diol isomer. Somewhat lower levels of stereochemical bias in the same direction were observed in pure water. However, further erosion of this trend was noted for those reactions performed in THF, such that a modest crossover in product distribution became apparent in certain examples. On the basis of competition experiments, both reaction trajectories give evidence of proceeding via chelated intermediates. The extent of stereoinduction was found to be in Line with the normal predilection of 2-cyclohexenones for axial attack, which is the process believed to be beset with minimal torsional effects. The substituents situated para to the ketone carbonyl do not exert a very large influence on product distribution, although electronic effects are evident in the context of the competition studies. A mechanistic model which integrates these findings is offered.

  DOI：

  10.1021/jo980825f
• 作为产物：
  描述：

  6-溴-1-四氢萘酮 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 四氢呋喃 、 水 为溶剂， 反应 2.25h， 以81%的产率得到6-bromo-3,4-dihydro-2-hydroxy-1(2H)-naphthalenone
  参考文献：
  名称：

  通过钯催化烯丙基碳酸烯丙酯的脱羧烯丙基烷基化 反应，不对称合成具有四取代α-立体异构中心的α-三氟甲氧基酮†

  摘要：

  钯催化的三氟甲氧基烯丙基烯醇碳酸酯的不对称脱羧烯丙基烷基化反应可得到富含对映体的α-三氟甲氧基烯丙基酮，其特征在于四取代的α-立体异构中心，具有优异的收率和高对映选择性。该方法进一步扩展到α-二氟甲氧基和α-甲氧基烯丙基酮的不对称合成，该合成在相似的催化条件下进行。

  DOI：

  10.1039/c8cc03131b

文献信息

• Asymmetric synthesis of α-trifluoromethoxy ketones with a tetrasubstituted α-stereogenic centre <i>via</i> the palladium-catalyzed decarboxylative allylic alkylation of allyl enol carbonates
  作者：Hiroya Kondo、Mayaka Maeno、Kazuki Hirano、Norio Shibata

  DOI：10.1039/c8cc03131b

  日期：——

  The palladium-catalyzed asymmetric decarboxylative allylic alkylation of trifluoromethoxy allyl enol carbonates afforded enantioenriched α-trifluoromethoxy allyl ketones that feature a tetrasubstituted α-stereogenic center in excellent yield and high enantioselectivity. The method was further extended to the asymmetric synthesis of α-difluoromethoxy and α-methoxy allyl ketones, which proceeded under

  钯催化的三氟甲氧基烯丙基烯醇碳酸酯的不对称脱羧烯丙基烷基化反应可得到富含对映体的α-三氟甲氧基烯丙基酮，其特征在于四取代的α-立体异构中心，具有优异的收率和高对映选择性。该方法进一步扩展到α-二氟甲氧基和α-甲氧基烯丙基酮的不对称合成，该合成在相似的催化条件下进行。
• Allylindation of 6-Substituted 2-Hydroxy-1-tetralones in Aqueous and Organic Media. Stereochemistry and Competition Studies
  作者：Paul C. Lobben、Leo A. Paquette

  DOI：10.1021/jo980825f

  日期：1998.10.1

  A systematic investigation of the stereoselectivity associated with coupling reactions involving the allylindium reagent-and 6-substituted 2-hydroxy-1-tetralones is presented. In each instance, the allylations were carried out in water, 50% aqueous THF, and dry THF. The extent of 1,2-induction was found to be highest-in THF-H2O (1:1) and to favor the trans diol isomer. Somewhat lower levels of stereochemical bias in the same direction were observed in pure water. However, further erosion of this trend was noted for those reactions performed in THF, such that a modest crossover in product distribution became apparent in certain examples. On the basis of competition experiments, both reaction trajectories give evidence of proceeding via chelated intermediates. The extent of stereoinduction was found to be in Line with the normal predilection of 2-cyclohexenones for axial attack, which is the process believed to be beset with minimal torsional effects. The substituents situated para to the ketone carbonyl do not exert a very large influence on product distribution, although electronic effects are evident in the context of the competition studies. A mechanistic model which integrates these findings is offered.