2-(4-phenylpiperazin-1-yl)benzaldehyde | 112253-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(4-phenylpiperazin-1-yl)benzaldehyde
• CAS: 112253-25-5
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: SLNGTNSKHBSCHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-phenylpiperazin-1-yl)benzaldehyde 在 N,N-二甲基丙烯基脲 作用下， 反应 6.0h， 以55%的产率得到1,4-二苯基哌嗪
  参考文献：
  名称：

  邻氨基苯甲醛的无催化剂光脱羰

  摘要：

  几乎共识是，醛基（–CHO）的脱羰不仅需要通过过渡金属催化剂来介导，而且还需要严格的反应条件（高温和长反应时间）。在这项工作中，受“基于构象选择性的”设计策略的启发，我们打破了这一共识，并发现了醛基的无催化剂光脱羰基。它表明，脱羰基化可以用可见光照射能够容易地实现通过引入叔胺到邻醛基的-位置。在温和条件下，我们的光脱羰基化可以耐受各种各样的叔胺。此外，在精心设计的特殊底物上进行机理和实验的（QM）计算表明，我们的光脱羰基取决于醛基和叔胺的构象特异性，并通过异常的[1,4] -H位移和随后的[1,3] -H移位。

  DOI：

  10.1039/d0gc01256d
• 作为产物：
  描述：

  N-苯基哌嗪 、 2-氟苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2-(4-phenylpiperazin-1-yl)benzaldehyde
  参考文献：
  名称：

  邻氨基苯甲醛的无催化剂光脱羰

  摘要：

  几乎共识是，醛基（–CHO）的脱羰不仅需要通过过渡金属催化剂来介导，而且还需要严格的反应条件（高温和长反应时间）。在这项工作中，受“基于构象选择性的”设计策略的启发，我们打破了这一共识，并发现了醛基的无催化剂光脱羰基。它表明，脱羰基化可以用可见光照射能够容易地实现通过引入叔胺到邻醛基的-位置。在温和条件下，我们的光脱羰基化可以耐受各种各样的叔胺。此外，在精心设计的特殊底物上进行机理和实验的（QM）计算表明，我们的光脱羰基取决于醛基和叔胺的构象特异性，并通过异常的[1,4] -H位移和随后的[1,3] -H移位。

  DOI：

  10.1039/d0gc01256d

文献信息

• A Novel Two-Step Synthesis of Hexahydropyrazino[1,2-α]-quinolines
  作者：Walter H. N. Nijhuis、Willem Verboom、David N. Reinhoudt

  DOI：10.1055/s-1987-28033

  日期：——

  The hexahydropyrazino[1,2-a]quinolines 2 were prepared in good yields by reaction of 2-(4-substituted 1-piperazinyl)benzaldehydes 5 with malononitrile and subsequent thermal cyclization of the condensation products 6; the latter reaction takes place via a concerted [1,5] hydrogen transfer and subsequent ring closure by addition of a carbanion to the iminium double bond.

  六氢吡嗪[1,2-a]喹啉2的合成产率良好，方法是将2-(4-取代1-哌嗪基)苯甲醛5与马来腈反应，随后对缩合产物6进行热环化；后者反应通过协同的[1,5]氢转移和随后通过羧阴离子加到亚胺双键上实现环闭合。
• Synthesis of Spiroheterocyclic Systems from Barbituric Acids and N,N-Disubstituted o-Aminobenzaldehydes
  作者：K. A. Krasnov、V. G. Kartsev

  DOI：10.1007/s11178-005-0263-2

  日期：2005.6

  Reactions of barbituric, 1,3-dimethylbarbituric, and 2-thiobarbituric acids with 2-(1-pyrrolidinyl)benzaldehyde, its 6- and 7-membered homologs, and 4-phenylpiperazine and morpholine analogs lead to formation of fused systems with a spirocyclic 2,4,6-trioxopyrimidine fragment. The process involves intermediate formation of labile 5-arylmethylidenebarbituric acids which exhibit t-amino effect and undergo spontaneous isomerization to give the final products. The observed spirocyclizations are characterized by an anomalously high rate.

  巴比妥酸、1,3-二甲基巴比妥酸和2-硫巴比妥酸与2-(1-吡咯烷基)苯甲醛及其6-和7-成员同系物，以及4-苯基哌嗪和吗啉类似物的反应，形成了具有螺环结构的2,4,6-三氧嘧啶片段的融合体系。该过程涉及不稳定的5-芳基甲烯基巴比妥酸的中间体形成，这些中间体表现出t-氨基效应，并自发异构化，生成最终产物。观察到的螺环化反应特征是反应速率异常高。
• Diastereoselective Spirocyclization via Intramolecular C( <i>sp</i> ³ )−H Bond Functionalization Triggered by Sequential [1,5]‐Hydride Shift/Cyclization Process: Approach to Spiro‐tetrahydroquinolines
  作者：Arup Bhowmik、Sumit Das、Writhabrata Sarkar、K. M. Saidalavi、Aniket Mishra、Anupama Roy、Indubhusan Deb

  DOI：10.1002/adsc.202001011

  日期：2021.2.2

  functionalization triggered by sequential [1,5]‐ hydride shift /cyclization sequence using ortho amino benzaldehydes and active methylene compounds such as 2‐coumaranone, 4‐hydroxycoumarin, 3‐coumaranone, and 3‐isochromanone. This protocol provides a Lewis acid catalyst‐free straight forward one‐pot reaction in cases of 2‐coumaranone and 4‐hydroxycoumarin, Lewis acid‐catalyzed stepwise reaction for 3‐coumaranone

  通过邻氨基苯甲醛和活性亚甲基化合物等连续的[1,5]-氢化物转移/环化序列引发的C（sp 3）-H键官能化，开发了螺[5.5]和[5.4]-四氢喹啉的直接合成物作为2-香豆酮，4-羟基香豆素，3-香豆酮和3-异苯并二氢吡喃酮。该方案可在2-香豆香酮和4-羟基香豆素的情况下提供无Lewis酸的简单直接反应，而Lewis酸催化的3-香豆香酮和3-isochromanone的逐步反应可在其中使用广泛的螺杂环优异的良率和非对映选择性。
• Design, synthesis and anticancer activity of functionalized spiro-quinolines with barbituric and thiobarbituric acids
  作者：Ravi Kiran Bhaskarachar、Vijayakumar G. Revanasiddappa、Subramanya Hegde、Janardhana P. Balakrishna、Suman Y. Reddy

  DOI：10.1007/s00044-015-1408-7

  日期：2015.9

  A new series of spiro-quinoline compounds have been accomplished by the reaction of barbituric acid or thiobarbituric acid with derivatives of benzisoxazole-5-carbaldehyde or 2-substituted benzaldehyde. These compounds were evaluated for their in vitro cytotoxicity on two mammalian cancer cell lines MCF-7 and KB. The compounds exhibit cytotoxicity against these cell lines in micromolar range. Among the series of compounds, 11(a-j) particularly 11b and 11e showed relatively good activity against both the tested cell lines. Compound 11b was found to exhibit the highest cytotoxic activity with IC50 value 90.2 mu M for MCF-7 and 49.8 mu M for KB cell line. Flow cytometric analysis study confirmed that these molecules induced cytotoxicity via apoptosis.
• Diastereoselective synthesis of 1-alkyl-2,4,6-trioxoperhydropyrimidine-5-spiro-3′-(1′,2′,3′,4′-tetrahydroquinolines)
  作者：Konstantin A. Krasnov、Victor G. Kartsev、Victor N. Khrustalev

  DOI：10.1016/j.tet.2010.06.015

  日期：2010.8

  Knoevenagel products formed by the condensation of N-monoalkyl barbituric acids with o-tert-amino benzaldehydes undergo tert-amino effect reactions (T-reactions) yielding 1-alkyl-2,4,6-trioxoperhydropyrimidine-5-spiro-3'-(1',2',3',4'-tetrahydroquinoline) derivatives as a mixture of (S*,S*)- and (S*,R*)-diastereomers. Mostly, the major diastereomer has the S*,S*-configuration. According to X-ray diffraction data in the solid form and NOE data in solution, diastereoselectivity of the T-reactions can be associated with the structure of the Knoevenagel products whose conformation is fixed by the strong intramolecular C-H center dot center dot center dot pi interaction. (c) 2010 Elsevier Ltd. All rights reserved.