3(N-benzylanilino)-6,6-dimethylcyclohex-2-enone | 152710-76-4

• 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: 3(N-benzylanilino)-6,6-dimethylcyclohex-2-enone
• 英文别名: 3-(N-benzylanilino)-6,6-dimethylcyclohex-2-en-1-one
• CAS: 152710-76-4
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: XKCKORWPVFBJMY-UHFFFAOYSA-N

物化性质

• 沸点：
  439.8±45.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3(N-benzylanilino)-6,6-dimethylcyclohex-2-enone 在 palladium on activated charcoal 六甲基磷酰三胺 、 ammonium formate 、 potassium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 1.08h， 生成 (6aR,11bR)-7-Benzyl-4,4-dimethyl-2,4,5,6,6a,7-hexahydro-1H-pyrrolo[2,3-d]carbazole
  参考文献：
  名称：

  Stereocontrolled formation of octahydro-1H-pyrrolo[2,3-d]carbazoles by reductive cyclization: total synthesis of (.+-.)-N-benzylaspidospermidine

  摘要：

  The synthesis of a series of 20-substituted octahydro-1H-pyrrolo[2,3-d]carbazoles 7, intermediates in the synthesis of Aspidosperma alkaloids, is described. Nonoxidative photocyclization of aryl enaminone 12 led to hexahydrocarbazol-4-ones 15a,b. Alkylation of the anions derived from 15a,b with KH and iodoacetonitrile gave rise to an undesirable intramolecular cyclization while reaction with LDA and nitroethylene as Michael acceptor afforded the trisubstituted hexahydrocarbazolones 21a,b. Reductive cyclization (H-2, PtO2) of cyano model compounds 16a,b and 17 provided octahydro-1H-pyrrolo[2,3-d]carbazoles 25 and 27 whose stereochemistry depended on hindrance of the alpha and beta face of the molecule. In contrast, reduction (HCOONH4, Pd/C, and then Na/EtOH) of nitro model compounds 18a,b and 19 via nitrones 22a,b and 23 and imine 24 led essentially to the more stable isomers 25B, 25C, and 27B with the natural stereochemistry at C-21. Reduction (HCOONH4, Pd/C) of nitro compounds 21a,b, which possess the elements for the future construction of the D and E rings, induced a tandem cyclization and afforded the pentacyclic iminium 30 which was converted by catalytic hydrogenation into (+/-)-N-benzylaspidospermidine (4). This compound was thus synthesized in seven steps from N-benzylaniline and cyclohexane-1,3-dione.

  DOI：

  10.1021/jo00075a049
• 作为产物：
  描述：

  3-(benzyl(phenyl)amino)cyclohex-2-en-1-one 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 4.0h， 生成 3(N-benzylanilino)-6,6-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Dugat, Denise; Gardette, Daniel; Gramain, Jean-Claude, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 1, p. 66 - 70

  摘要：

  DOI：

文献信息

• Efficient photochemical synthesis of tricyclic keto‐indoles
  作者：Christèle Tietcheu、Christophe Garcia、Daniel Gardette、Denise Dugat、Jean‐Claude Gramain

  DOI：10.1002/jhet.5570390517

  日期：2002.9

  Tricyclic keto-indoles were synthesized by photocyclization of easily obtained enaminones in an electro-cyclic photochemical reaction. The three methods reported were chosen according to the enaminone structure. The most general procedure using one-step synthesis was carried out in a benzene-methanol solution in the presence of sodium methylate. In the case of base sensitive substrates, the best method

  在环光化学反应中，通过容易获得的烯胺酮的光环化反应合成了三环酮吲哚。根据烯胺酮结构选择报道的三种方法。使用一步合成的最通用方法是在甲醇钠存在下的苯甲醇溶液中进行的。对于碱敏感的底物，最好的方法是光环化然后氧化。此外，通过光解反应制备了具有五元环的N-未取代的吲哚。这三种方法都是高效且易于执行的。