3-nitro-6-(1-piperidinyl)benzoic acid methyl ester | 81215-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-nitro-6-(1-piperidinyl)benzoic acid methyl ester
• 英文别名: 5-Nitro-2-piperidino-benzoesaeuremethylester；2-(1-piperidinyl)-5-nitro-benzoic zcid, methyl ester；methyl 5-nitro-2-(piperidin-1-yl)benzoate；Methyl 5-nitro-2-piperidin-1-ylbenzoate
• CAS: 81215-40-9
• 化学式: C₁₃H₁₆N₂O₄
• mdl: MFCD06204024
• 分子量: 264.281
• InChiKey: NTFPFLYEVXOCHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitro-6-(1-piperidinyl)benzoic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 5-硝基-2-哌啶-1-基苯甲酸
  参考文献：
  名称：

  Discovery of 4-benzoylpiperidine and 3-(piperidin-4-yl)benzo[d]isoxazole derivatives as potential and selective GlyT1 inhibitors

  摘要：

  两个系列的潜在和选择性GlyT1抑制剂通过生物同位素替代被发现。23q在慢性PCP处理的类精神分裂症行为模型上有效。

  DOI：

  10.1039/c5ra04714e
• 作为产物：
  描述：

  2-羟基-5-硝基苯甲酸甲酯 在 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 0.41h， 生成 3-nitro-6-(1-piperidinyl)benzoic acid methyl ester
  参考文献：
  名称：

  Discovery of 4-benzoylpiperidine and 3-(piperidin-4-yl)benzo[d]isoxazole derivatives as potential and selective GlyT1 inhibitors

  摘要：

  两个系列的潜在和选择性GlyT1抑制剂通过生物同位素替代被发现。23q在慢性PCP处理的类精神分裂症行为模型上有效。

  DOI：

  10.1039/c5ra04714e

文献信息

• Intramolekulare Umsetzung von Iminiumverbindungen mit Carbonsäuren
  作者：Hans Möhrle、Manfred Busch

  DOI：10.1002/ardp.19823150204

  日期：——

  In 2‐Stellung mit cyclischen Aminen substituierte 5‐Nitrobenzoesäuren wurden mit Quecksilber(II)‐EDTA dehydriert. Während das Piperidin‐ und Perhydroazepin‐Derivat unter normalen Bedingungen jeweils das tricyclische Oxazinon bei nur geringer Decarboxylierungsrate lieferte, konnte das Pyrrolidin‐Derivat lediglich in unüblichen Lösungsmitteln umgesetzt werden, wobei hauptsächlich Verlust der Carboxylfunktion

  在 2-Stellung mit cyclischen Aminen substituierte 5-Nitrobenzoesäuren wurden mit Quecksilber(II)-EDTA dehydriert。WährendDAS哌啶UND全氢化吖 - 衍生金融工具的Unter normalen Bedingungen jeweils DAS tricyclische Oxazinon北泡子格林格Decarboxylierungsrate lieferte，konnte DAS吡咯 - 衍生金融工具lediglich在unüblichenLösungsmittelnumgesetzt werden，wobeihauptsächlichVerlust德Carboxylfunktion UND罗布泊geringemAusmaßDehydrierung eintrat。Im Hinblick
• Synthesis and structure activity relationship studies of novel Staphylococcus aureus Sortase A inhibitors
  作者：Bala Chandra Chenna、Jason R. King、Bidhan A. Shinkre、Amanda L. Glover、Aaron L. Lucius、Sadanandan E. Velu

  DOI：10.1016/j.ejmech.2010.05.024

  日期：2010.9

  Synthetic methods have been developed for lead Sortase A inhibitors identified from previous studies. Several derivatives of the lead inhibitor were synthesized to derive preliminary structure activity relationships (SAR). Different regions of the lead inhibitor that are critical for the enzyme activity have been determined by systematic SAR studies. The E stereochemistry of the lead compound was found to be critical for its activity. Replacement of the E double bond with Z double bond or a rigid triple bond reduced the enzyme inhibitory activity in most cases. Reduction of the double bond to a C-C single bond resulted in complete loss of activity. Amide carbonyl and NH groups were also found to be crucial for the activity of this class of inhibitors, as well. The morpholine ring oxygen atom was also found to be an important factor for the activity of the lead inhibitor. Preliminary SAR studies led to the identification of compounds with improved enzyme inhibition. The most active compound was found to have an IC(50) value of 58 mu M against the enzyme. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Demonstrating the Synergy of Synthetic, Mechanistic, and Computational Studies in a Regioselective Aniline Synthesis
  作者：Ian W. Davies、Jean-François Marcoux、Jeffery T. Kuethe、Michael D. Lankshear、Jeremy D. O. Taylor、Nancy Tsou、Peter G. Dormer、David L. Hughes、K. N. Houk、Vildan Guner

  DOI：10.1021/jo035677u

  日期：2004.2.1

  Tri- and tetrasubstituted anilines are formed in good to excellent yields by the addition of ketones to vinamidinium salts (up to 98%). The reaction proceeds via the formation of dienone intermediates, which react to form an enamine with the liberated amine. In the case of a nitro, or dimethylaminomethylene substituent, the enamines undergo a facile electrocyclic ring closure to form a cyclohexadiene, which goes on to form anilines with a high degree of selectivity (up to 50:1) with a minor competing pathway proceeding via the enol providing phenols. Competition experiments using isotopic substitution reveal that the rate determining step en route to dienone is enol/enolate addition to the vinamidinium salt, which is characterized by an inverse secondary isotope effect (k(H/D) 0.7-0.9). Computational studies have been used to provide a framework for understanding the reaction pathway. The original proposal for a [1,5]-H shift was ruled out on the basis of the calculations, which did not locate a thermally accessible transition state. The minimum energy conformation of the enamine is such that a facile electrocyclic ring closure is ensured, which is corroborated by the experimental studies. A framework for understanding the reaction pathway is presented.
• An Unexpected [1,5]-H Shift in the Synthesis of Nitroanilines
  作者：Ian W. Davies、Jean-François Marcoux、Jeremy D. O. Taylor、Peter G. Dormer、Robert J. Deeth、Félix-Antoine Marcotte、David L. Hughes、Paul J. Reider

  DOI：10.1021/ol0265362

  日期：2002.8.1