N-benzyl-2-phenyl-2-cyclohexen-1-ylamine | 189363-81-3

• 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-benzyl-2-phenyl-2-cyclohexen-1-ylamine
• 英文别名: Benzenemethanamine, N-(2-phenyl-2-cyclohexen-1-yl)-；N-benzyl-2-phenylcyclohex-2-en-1-amine
• CAS: 189363-81-3
• 化学式: C₁₉H₂₁N
• 分子量: 263.382
• InChiKey: MVTULIPXXVEKGE-UHFFFAOYSA-N

物化性质

• 沸点：
  403.2±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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-benzyl-2-phenyl-2-cyclohexen-1-ylamine 在 2,3,4,5,6-五氟碘苯 、 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以71%的产率得到N-benzyl-[1,1'-biphenyl]-2-amine
  参考文献：
  名称：

  光催化脱氢合成N-芳基胺

  摘要：

  通过可见光光氧化还原催化的催化脱氢（CD）为芳香族化合物的合成提供了一条有效的途径。然而，由于在光催化条件下难以控制胺的反应性，通过可见光诱导的环糊精来获得广泛使用的合成部分的N-芳基胺仍然是一个重大挑战。在这里，可见光诱导光催化合成N-芳基胺是通过烯丙胺的CD实现的。使用C 6 F 5 I作为氢原子受体的不寻常策略使得带有各种官能团和活化C-H键的胺能够温和且受控的CD，从而抑制反应性N-芳基胺产物的副反应。彻底的机理研究表明，单电子和氢原子转移以明确的顺序参与，以在控制反应性方面提供协同效应。值得注意的是，反电子转移过程可防止所需产物在氧化条件下进一步反应。

  DOI：

  10.1039/d0sc04890a
• 作为产物：
  描述：

  2-phenylcyclohex-2-enol 在 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.5h， 生成 N-benzyl-2-phenyl-2-cyclohexen-1-ylamine
  参考文献：
  名称：

  Total Syntheses of (−)-Mesembrane and (−)-Mesembrine via Palladium-Catalyzed Enantioselective Allylic Substitution and Zirconium-Promoted Cyclization

  摘要：

  4-Arylhexahydroindole derivatives 5 were synthesized from 2-arylcyclohexenyl allylamine derivatives 4, which have a large protecting group on nitrogen, using zirconium-promoted cyclization. Reaction of 4e with Cp2ZrBu2, followed by treatment with MeMgBr and then O-2, gave 2a in 63% yield by a one-pot reaction, since the approach of Oz to zirconium was prevented by the aryl group. The total syntheses of (+/-)-mesembrane and (+/-)-mesembrine were achieved starting from 2a. To synthesize these natural products in a chiral form, the starting allylamine derivative 24 (80% yield, 86% ee, recrystallized from MeOH, 99% ee with 79% recovery) was prepared from allyl carbonate 22a and N-tosylallylamine 23 using palladium-catalyzed asymmetric amination in the presence of (S)-BINAPO as a chiral ligand. (-)-Mesembrane and (-)-mesembrine were synthesized from this allylamine 24.

  DOI：

  10.1021/jo9701187

文献信息

• A Convenient Method for the Synthesis of β,γ-Unsaturated Amines from Alkenes via α,β-Unsaturated Diphenylsulfonium Salts
  作者：Hiroyuki Yamanaka、Jun-ichi Matsuo、Asahi Kawana、Teruaki Mukaiyama

  DOI：10.1246/cl.2003.626

  日期：2003.7

  1,1-Disubstituted and trisubstituted alkenes were converted into the corresponding β,γ-unsaturated amines 4 via three steps: the initial formation of α,β-unsaturated diphenylsulfonium triflates 2 from alkenes and diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1), followed by double bond migration of 2 to β,γ-unsaturated sulfonium triflates 3 with primary or secondary amines

  1,1-二取代和三取代烯烃通过三个步骤转化为相应的 β,γ-不饱和胺 4：由烯烃和二苯基（三氟甲磺酰氧基）锍三氟甲磺酸盐（1）初步形成 α,β-不饱和二苯锍三氟甲磺酸盐 2，然后通过 2 与伯胺或仲胺的双键迁移至 β,γ-不饱和锍三氟甲磺酸盐 3，以及 3 与这些胺的连续亲核取代。
• Total Syntheses of (−)-Mesembrane and (−)-Mesembrine <i>via</i> Palladium-Catalyzed Enantioselective Allylic Substitution and Zirconium-Promoted Cyclization
  作者：Miwako Mori、Shinji Kuroda、Chang-Shan Zhang、Yoshihiro Sato

  DOI：10.1021/jo9701187

  日期：1997.5.1

  4-Arylhexahydroindole derivatives 5 were synthesized from 2-arylcyclohexenyl allylamine derivatives 4, which have a large protecting group on nitrogen, using zirconium-promoted cyclization. Reaction of 4e with Cp2ZrBu2, followed by treatment with MeMgBr and then O-2, gave 2a in 63% yield by a one-pot reaction, since the approach of Oz to zirconium was prevented by the aryl group. The total syntheses of (+/-)-mesembrane and (+/-)-mesembrine were achieved starting from 2a. To synthesize these natural products in a chiral form, the starting allylamine derivative 24 (80% yield, 86% ee, recrystallized from MeOH, 99% ee with 79% recovery) was prepared from allyl carbonate 22a and N-tosylallylamine 23 using palladium-catalyzed asymmetric amination in the presence of (S)-BINAPO as a chiral ligand. (-)-Mesembrane and (-)-mesembrine were synthesized from this allylamine 24.
• Synthesis of <i>N</i>-aryl amines enabled by photocatalytic dehydrogenation
  作者：Jungwon Kim、Siin Kim、Geunho Choi、Geun Seok Lee、Donghyeok Kim、Jungkweon Choi、Hyotcherl Ihee、Soon Hyeok Hong

  DOI：10.1039/d0sc04890a

  日期：——

  Catalytic dehydrogenation (CD) via visible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access to N-aryl amines, which are widely utilized synthetic moieties, via visible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced

  通过可见光光氧化还原催化的催化脱氢（CD）为芳香族化合物的合成提供了一条有效的途径。然而，由于在光催化条件下难以控制胺的反应性，通过可见光诱导的环糊精来获得广泛使用的合成部分的N-芳基胺仍然是一个重大挑战。在这里，可见光诱导光催化合成N-芳基胺是通过烯丙胺的CD实现的。使用C 6 F 5 I作为氢原子受体的不寻常策略使得带有各种官能团和活化C-H键的胺能够温和且受控的CD，从而抑制反应性N-芳基胺产物的副反应。彻底的机理研究表明，单电子和氢原子转移以明确的顺序参与，以在控制反应性方面提供协同效应。值得注意的是，反电子转移过程可防止所需产物在氧化条件下进一步反应。