N-methyl-N-(5,6,7,8-tetrahydro-5-methylene-2-naphthyl)acetamide | 213249-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-methyl-N-(5,6,7,8-tetrahydro-5-methylene-2-naphthyl)acetamide
• 英文别名: N-methyl-N-(5-methylidene-7,8-dihydro-6H-naphthalen-2-yl)acetamide
• CAS: 213249-33-3
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: WTSZZUIDSMESJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(5,6,7,8-tetrahydro-5-methylene-2-naphthyl)acetamide 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 水杨酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以79%的产率得到N-methyl-N-(5,6,7,8-tetrahydro-6-hydroxy-5-methylene-2-naphthyl)acetamide
  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：

  5,6,7,8-四氢萘-2-基乙胺 在 chromium(VI) oxide 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 甲苯 、 苯 为溶剂， 反应 24.0h， 生成 N-methyl-N-(5,6,7,8-tetrahydro-5-methylene-2-naphthyl)acetamide
  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

文献信息

• 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.