N-methyl-N-(5,6,7,8-tetrahydro-2-naphthyl)acetamide | 213249-32-2

• 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-2-naphthyl)acetamide
• 英文别名: N-(1,2,3,4-tetrahydronaphthalen-6-yl)-N-methylacetamide；N-Acetyl-6-methylamino-1,2,3,4-tetrahydronaphthalin；6-(Methyl-acetyl-amino)-tetralin；N-Methyl-N-(5,6,7,8-tetrahydro-[2]naphthyl)-acetamid；N-methyl-N-(5,6,7,8-tetrahydronaphthalen-2-yl)acetamide
• CAS: 213249-32-2
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: JVRVXDPYEFZUJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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-2-naphthyl)acetamide 在 chromium(VI) oxide 、 叔丁基过氧化氢 、 selenium(IV) oxide 、 水杨酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 16.0h， 生成 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：

  1,2,3,4-四氢-6-硝基萘 在 1,2,3,4-四氢萘 、 氢气 、 sodium 、 镍 、 甲苯 作用下， 生成 N-methyl-N-(5,6,7,8-tetrahydro-2-naphthyl)acetamide
  参考文献：
  名称：

  Schroeter, Justus Liebigs Annalen der Chemie, 1922, vol. 426, p. 132

  摘要：

  DOI：

文献信息

• Titanium(IV) Chloride Promoted Syntheses of New Imidazo[1,2-<i>a</i>]pyridine Derivatives under Microwave Conditions
  作者：Lisheng Cai、Chad Brouwer、Kathryn Sinclair、Jessica Cuevas、Victor W. Pike

  DOI：10.1055/s-2005-918490

  日期：——

  imidazo[1,2-a]pyridine derivatives from the reaction of 2-aminopyridines with α-haloketones. The critical reagent is titanium(IV) chloride, which appears to serve as a strongdehydrating agent to promote formation of putative Schiff base intermediates, which cyclize subsequently to form the products. The reactions were performed rapidly under microwave conditions. Multiple reaction conditions were evaluated

  描述了一种由 2-氨基吡啶与 α-卤代酮反应合成咪唑并[1,2-a]吡啶衍生物的新方法。关键试剂是氯化钛 (IV)，它似乎是一种强脱水剂，可促进推定的席夫碱中间体的形成，后者随后环化形成产物。反应在微波条件下快速进行。评估了多种反应条件，包括反应温度、溶剂和其他路易斯酸。检查了 α-卤代酮和 2-氨基吡啶底物中取代模式的各种组合，以评估反应的范围。该反应对两种底物中的取代基都非常敏感，尤其是那些具有碱性或配位能力的底物。