N-(3-phenoxybenzyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-phenoxybenzyl)acetamide
• 英文别名: (m-phenoxybenzyl)acetamide；N~1~-(3-Phenoxybenzyl)acetamide；N-[(3-phenoxyphenyl)methyl]acetamide
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: CQQBITKCIASFJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酰胺 、 间苯氧基苯甲醛 在 dirhodium tetraacetate 、 一氧化碳 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以74%的产率得到N-(3-phenoxybenzyl)acetamide
  参考文献：
  名称：

  原子经济无氢还原酰胺化与穷举还原胺化的二分法

  摘要：

  已经开发了Rh催化的醛的一步还原酰胺化。该方案不需要外部氢源，并使用一氧化碳作为脱氧剂。只需改变溶剂即可改变反应方向：在THF中反应可生成酰胺，而甲醇则有利于叔胺的形成。

  DOI：

  10.1021/acs.orglett.7b02821

文献信息

• Photochemistry of phenoxybenzyl alcohols in aqueous solution: photosolvolysis vs. photorearrangement to 6H-dibenzo[b,d]pyrans
  作者：C. G. Huang、Peter Wan

  DOI：10.1021/jo00016a009

  日期：1991.8

  The photochemistry of three phenoxybenzyl alcohols (1-3) has been studied in MeOH, CH3CN, and in aqueous solution. It was found that both of the ortho-substituted phenoxybenzyl alcohols 1 and 2 gave the corresponding 6H-dibenzo[b,d]pyrans 6 and 10, via a mechanism believed to involve initial aryl C-O bond homolysis followed by rearrangement to give a 2-(2'-hydroxyphenyl)benzyl alcohol (biphenyl) derivative, which subsequently undergoes a photocyclization reaction to the corresponding 6H-dibenzo[b,d]pyran. The quantum yield for formation of 6 (from 1) was 0.0073 in neutral 6:4 H2O-CH3CN. Lower quantum yields for formation of 6 were observed on photolysis in pure organic solvents (PHI = 0.0015 in 100% CH3CN). The meta-substituted isomer 3 did not give any reaction via a similar photocyclization process: its photochemistry involves initial aryl C-O bond homolysis followed by simple radical recoupling to give isomeric hydroxybiphenyls, as well as products derived from radical escape. In aqueous sulfuric acid solution (pH < 2), a competing acid-catalyzed photosolvolysis reaction was observed for all of these compounds (i.e., C-OH bond heterolysis with assistance of hydronium ion); it was the only observed reaction in moderately concentrated sulfuric acid solution.
• Dichotomy of Atom-Economical Hydrogen-Free Reductive Amidation vs Exhaustive Reductive Amination
  作者：Pavel N. Kolesnikov、Dmitry L. Usanov、Karim M. Muratov、Denis Chusov

  DOI：10.1021/acs.orglett.7b02821

  日期：2017.10.20

  Rh-catalyzed one-step reductive amidation of aldehydes has been developed. The protocol does not require an external hydrogen source and employs carbon monoxide as a deoxygenative agent. The direction of the reaction can be altered simply by changing the solvent: reaction in THF leads to amides, whereas methanol favors formation of tertiary amines.

  已经开发了Rh催化的醛的一步还原酰胺化。该方案不需要外部氢源，并使用一氧化碳作为脱氧剂。只需改变溶剂即可改变反应方向：在THF中反应可生成酰胺，而甲醇则有利于叔胺的形成。