N-methyl-N-(benzyl-α,α-d2)formamide | 135108-23-5

• 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-methyl-N-(benzyl-α,α-d2)formamide
• CAS: 135108-23-5
• 化学式: C₉H₁₁NO
• 分子量: 151.177
• InChiKey: ACVHDOLKAPAIGB-RJSZUWSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  ethyl N-(benzyl-α,α-d2)carbamate 在 lithium aluminium tetrahydride 、 3,7,8,10-四甲基-苯并[g]蝶啶-2,4(3H,10H)-二酮 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 88.0h， 生成 N-methyl-N-(benzyl-α,α-d2)formamide
  参考文献：
  名称：

  Amine-flavin electron transfer photochemistry. Potential models for monoamine oxidase catalysis and inhibition

  摘要：

  The photoreactions of 3-methyllumiflavin (3MLF) and a variety of amines have been explored. These studies have demonstrated that 3MLF undergoes efficient photoreactions with alpha-silyl tertiary benzylamines to generate 4a-adducts by pathways involving sequential SET and desilylation followed by radical coupling. These adducts are unstable substances that react rapidly with nucleophiles (e.g., MeOH, H2O, and NaBH4) and oxygen. They are also photolabile, providing the corresponding 4a-benzyldihydroflavin upon irradiation. Non-silicon-containing primary and secondary amines also participate in SET-promoted photoreactions with 3MLF. The amine cation radicals formed in these processes undergo further transformations to produce radical intermediates by either alpha-CH or NH deprotonation pathways. The potential relevance of these findings to the area of monoamine oxidase chemistry is considered.

  DOI：

  10.1021/jo00016a026

文献信息

• Oxygenation of Benzyldimethylamine by Singlet Oxygen. Products and Mechanism
  作者：Enrico Baciocchi、Tiziana Del Giacco、Andrea Lapi

  DOI：10.1021/ol047876l

  日期：2004.12.1

  study of the reaction of benzyldimethylamine (1) with thermally and photochemically generated 1O2 in MeCN was carried out. Benzaldehyde and N-benzyl-N-methylformamide are the reaction products, oxygenation representing ca. 9% of the overall quenching of 1O2 by 1. The temperature effect and the intermolecular and intramolecular kinetic deuterium isotope effects were also determined. It is suggested

  [反应：见正文]进行了苄基二甲基胺（1）与热和光化学生成的1O2在MeCN中反应的产物研究。苯甲醛和N-苄基-N-甲基甲酰胺是反应产物，氧合代表约。1O2整体淬灭的9％。还测定了温度效应以及分子间和分子内动力学氘同位素效应。建议产物源自可逆形成的电荷转移络合物中的内部络合物氢原子转移。