3-(Chloromethyl)-2-aza-3-azonia-4-azanidatricyclo[7.3.1.05,13]trideca-1(12),2,5,7,9(13),10-hexaene | 291301-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(Chloromethyl)-2-aza-3-azonia-4-azanidatricyclo[7.3.1.05,13]trideca-1(12),2,5,7,9(13),10-hexaene
• CAS: 291301-36-5
• 化学式: C₁₁H₈ClN₃
• 分子量: 217.658
• InChiKey: CUGCPSRQEDFBFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  16.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(Chloromethyl)-2-aza-3-azonia-4-azanidatricyclo[7.3.1.05,13]trideca-1(12),2,5,7,9(13),10-hexaene 、 2,3,4-三甲氧基苯甲醛 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到2-(2-Aza-3-azonia-4-azanidatricyclo[7.3.1.05,13]trideca-1(12),2,5,7,9(13),10-hexaen-3-yl)-1-(2,3,4-trimethoxyphenyl)ethanol
  参考文献：
  名称：

  An α-aminomethyl carbanion equivalent via a novel Barbier reaction: (1H-naphtho[1,8-de]-1,2,3-triazin-2-yl)methyl anion

  摘要：

  A novel sonication-promoted Barbier reaction putatively generated the titled species from the corresponding naphthotriazinylmethyl chloride and magnesium in THF: its formal addition to a variety of carbonyl compounds in situ occurred in excellent yields. Subsequent catalytic hydrogenolysis of the triazine moiety demasked the amine, thus defining a route to various phenylethylamines (including the alkaloid 'mescaline'), or ethanolamines (in two cases), in excellent overall yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00689-4
• 作为产物：
  描述：

  2-methyl-2H-naphto<1,8-de>triazine 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 3-(Chloromethyl)-2-aza-3-azonia-4-azanidatricyclo[7.3.1.05,13]trideca-1(12),2,5,7,9(13),10-hexaene
  参考文献：
  名称：

  An α-aminomethyl carbanion equivalent via a novel Barbier reaction: (1H-naphtho[1,8-de]-1,2,3-triazin-2-yl)methyl anion

  摘要：

  A novel sonication-promoted Barbier reaction putatively generated the titled species from the corresponding naphthotriazinylmethyl chloride and magnesium in THF: its formal addition to a variety of carbonyl compounds in situ occurred in excellent yields. Subsequent catalytic hydrogenolysis of the triazine moiety demasked the amine, thus defining a route to various phenylethylamines (including the alkaloid 'mescaline'), or ethanolamines (in two cases), in excellent overall yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00689-4

文献信息

• An α-aminomethyl carbanion equivalent via a novel Barbier reaction: (1H-naphtho[1,8-de]-1,2,3-triazin-2-yl)methyl anion
  作者：Sosale Chandrasekhar、Malayalam Sridhar

  DOI：10.1016/s0040-4039(00)00689-4

  日期：2000.6

  A novel sonication-promoted Barbier reaction putatively generated the titled species from the corresponding naphthotriazinylmethyl chloride and magnesium in THF: its formal addition to a variety of carbonyl compounds in situ occurred in excellent yields. Subsequent catalytic hydrogenolysis of the triazine moiety demasked the amine, thus defining a route to various phenylethylamines (including the alkaloid 'mescaline'), or ethanolamines (in two cases), in excellent overall yields. (C) 2000 Elsevier Science Ltd. All rights reserved.