1-Benzoyl-4-phenyl-1,2,5,6-tetrahydropyridine | 1257268-45-3

• 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: 1-Benzoyl-4-phenyl-1,2,5,6-tetrahydropyridine
• 英文别名: phenyl-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)methanone
• CAS: 1257268-45-3
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: CNFUXJHCOAYGKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Benzoyl-4-phenyl-1,2,5,6-tetrahydropyridine 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 4-苯基吡啶
  参考文献：
  名称：

  Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines

  摘要：

  A novel method for the synthesis of 1,2,4-trisubstituted- or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6-tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF(3)-OEt(2))-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.131
• 作为产物：
  描述：

  4-苯基-1,2,3,6-四氢吡啶 、 苯甲酸 在 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 以69 %的产率得到1-Benzoyl-4-phenyl-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  TBAT 催化叔酰胺脱氧还原为胺

  摘要：

  开发了一种简单、温和、无金属的催化方案，将酰胺转化为胺。该方案使用稳定的二氟三苯基硅酸四丁基铵与硅烷结合，产生高反应性的氢硅酸盐物质，从而能够以中等至良好的产率将多种酰胺还原为胺。该协议的吸引人的特点包括操作简单、安全、反应时间短、室温反应、底物范围广泛且易于放大。

  DOI：

  10.1021/acs.orglett.3c01150

文献信息

• Selectfluor-promoted fluorination of piperidinyl olefins
  作者：Meng-Yang Chang、Nien-Chia Lee、Ming-Fang Lee、Yu-Ping Huang、Chung-Han Lin

  DOI：10.1016/j.tetlet.2010.08.090

  日期：2010.11

  4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate (Selectfluor) is reported. Two transformations from endo-olefin 1 to allylic fluoride 3 and from exo-olefin 2 to fluorohydrin 6 proceed via allylic fluorination and fluorohydroxylation in moderate yields. It presents two novel reactions promoted by Selectfluor and broadens the scope of application.

  通过哌啶子基外表皮的处理，简单而直接地合成1-取代的4-芳基-5-氟-1,2,3,6-四氢吡啶（3）或1-取代的4-二芳基甲酰基-4-氟哌啶（6）-或内烯烃与1-氯甲基-4-氟-1,4-二氮鎓双环[2.2.2]辛烷双（四氟硼酸盐（的Selectfluor）报道从两次转变。内切α-烯烃1至烯丙基氟化物3和从外烯烃2至氟代醇6通过烯丙基氟化和氟羟基化进行中等收率。它展示了Selectfluor促进的两个新颖反应，并扩大了应用范围。
• Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines
  作者：Meng-Yang Chang、Ming-Fang Lee、Nien-Chia Lee、Yu-Ping Huang、Chung-Han Lin

  DOI：10.1016/j.tetlet.2010.11.131

  日期：2011.2

  A novel method for the synthesis of 1,2,4-trisubstituted- or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6-tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF(3)-OEt(2))-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol. (C) 2010 Elsevier Ltd. All rights reserved.
• TBAT-Catalyzed Deoxygenative Reduction of Tertiary Amides to Amines
  作者：Vinothkumar Vinayagam、Subir Kumar Sadhukhan、Satish Kumar Karre、Ravuri Srinath、Ravi Kumar Maroju、Purushotham Reddy Karra、Hema Sundar Naveen Babu Bathula、Siva Kundrapu、Srikanth Reddy Surukonti

  DOI：10.1021/acs.orglett.3c01150

  日期：2023.6.30

  developed to convert amides to amines. This protocol uses a stable tetrabutylammonium difluorotriphenylsilicate in combination with silanes that generates a highly reactive hydrosilicate species, which enables the reduction of a broad range of amides to amines in moderate to good yields. The attractive features of this protocol include operational simplicity, safety, short reaction times, room temperature

  开发了一种简单、温和、无金属的催化方案，将酰胺转化为胺。该方案使用稳定的二氟三苯基硅酸四丁基铵与硅烷结合，产生高反应性的氢硅酸盐物质，从而能够以中等至良好的产率将多种酰胺还原为胺。该协议的吸引人的特点包括操作简单、安全、反应时间短、室温反应、底物范围广泛且易于放大。