| 137596-57-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 137596-57-7；137693-43-7
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: FHPZYKBQZDCOIJ-HJCZWSGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (1R,2S)-2-苯基环丙胺 以 甲醇 、 乙腈 为溶剂， 反应 1.17h， 生成
  参考文献：
  名称：

  SET photochemistry of flavin-cyclopropylamine systems. Models for proposed monoamine oxidase inhibition mechanisms

  摘要：

  Single electron transfer (SET) induced photochemical reactions of 3-methyllumiflavin (3-MLF) with the cyclo-propylamines, trans-2-phenylcyclopropylamine (1) and 1-phenylcyclopropylamine (4), have been explored with the aim of defining the nature of and mechanisms for the reaction pathways followed, The excited-state SET processes probed in this investigation were designed to model those proposed previously for inactivation of the flavine-containing enzyme, monoamine oxidase, by these same cyclopropylamines. Irradiation of 3-MLF in an N2-purged solution containing cyclopropylamine 4 leads to generation of the C-4a,N-5-propanodihydroflavin 14 as the major primary photoproduct. This substance, which is formed by an SET-promoted radical coupling mechanism, is transformed to the C-4a-(benzoylethyl)dihydroflavin 6 under hydrolytic conditions. Several other minor, cyclopropylamine-derived products are also generated in this reaction, again via radical pathways. In contrast, irradiation of an air-saturated solution of 3-MLF and 4 produces the epoxy ketone 8 efficiently. In this reaction, 3-MLF serves as an SET photosensitizer for the oxidative ring-opening reaction that converts 4 to 8. Finally, the C-4a,N-5-propanodihydroflavin adducts 17 and 18 are generated along with substances arising by secondary reaction of a primary product, cinnamaldehyde (20), when 3-MLF is irradiated in an N2-purged solution containing the cyclopropylamine 1. Mechanistic aspects of these bona ride SET flavin-cyclopropylamine reactions and their possible relationship to proposals made earlier about the nature of and mechanisms for monoamine oxidase inactivation by the same cyclopropylamines are discussed.

  DOI：

  10.1021/ja00024a034