N-methyl-N-(benzyl-α,α-d2)amine | 62908-51-4

• 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)amine
• 英文别名: N-methylbenzylamide；1,1-dideuterio-N-methyl-1-phenylmethanamine
• CAS: 62908-51-4
• 化学式: C₈H₁₁N
• 分子量: 123.166
• InChiKey: RIWRFSMVIUAEBX-RJSZUWSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(benzyl-α,α-d2)amine 以 乙腈 为溶剂， 反应 68.0h， 生成 4a-hydroxy-5-(benzyl-α,α-d2)-4a,5-dihydro-3-methyllumiflavin
  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
• 作为产物：
  描述：

  ethyl N-(benzyl-α,α-d2)carbamate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以98%的产率得到N-methyl-N-(benzyl-α,α-d2)amine
  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

• Insertion of Arynes into <i>N</i>-Halo Bonds: A Direct Approach to <i>o</i>-Haloaminoarenes
  作者：Charles E. Hendrick、Stacey L. McDonald、Qiu Wang

  DOI：10.1021/ol401518c

  日期：2013.7.5

  A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a nitrogen-halide bond (N-X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized a minoarene derivatives.
• Reactions of N-(arylsulfonoxy)-N-benzylmethylamines with sodium methoxide in methanol
  作者：Bong Rae Cho、Sang Yong Pyun、Tae Rin Kim

  DOI：10.1021/ja00260a015

  日期：1987.12
• Cho, Bong Rae; Namgoong, Sung Keon; Kim, Tae Rin, Journal of the Chemical Society. Perkin transactions II, 1987, p. 853 - 856
  作者：Cho, Bong Rae、Namgoong, Sung Keon、Kim, Tae Rin

  DOI：——

  日期：——
• Reactions of N-halobenzylalkylamines with sodium methoxide in methanol
  作者：Bong Rae Cho、Jong Chan Yoon、Richard A. Bartsch

  DOI：10.1021/jo00224a059

  日期：1985.11
• CHO, BONG RAE;NAMGOONG, SUNG KEON;KIM, TAE RIN, J. CHEM. SOC. PERKIN TRANS.,(1987) N 7, 853-856
  作者：CHO, BONG RAE、NAMGOONG, SUNG KEON、KIM, TAE RIN

  DOI：——

  日期：——