tert-butyl 4-(2,4-dichlorophenyl)-3,6-dihydro-2H-pyridine-1-carboxylate | 138647-54-8

• 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: tert-butyl 4-(2,4-dichlorophenyl)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 138647-54-8
• 化学式: C₁₆H₁₉Cl₂NO₂
• 分子量: 328.238
• InChiKey: XNZBKPOHOWFAAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  413.0±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2,4-dichlorophenyl)-3,6-dihydro-2H-pyridine-1-carboxylate 在 platinum(IV) oxide 、 氢气 、 盐酸 作用下， 以 乙醇 、 1,4-二氧六环 为溶剂， 生成 4-(2,4-Dichlorophenyl)-piperidine
  参考文献：
  名称：

  4-Aryl piperazine and piperidine amides as novel mGluR5 positive allosteric modulators

  摘要：

  Positive allosteric modulation of metabotropic glutamate receptor 5 (mGluR5) is regarded as a potential novel treatment for schizophrenic patients. Herein we report the synthesis and SAR of 4-aryl piperazine and piperidine amides as potent mGluR5 positive allosteric modulators (PAMs). Several analogs have excellent activity and desired drug-like properties. Compound 2b was further characterized as a PAM using several in vitro experiments, and produced robust activity in several preclinical animal models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.036
• 作为产物：
  描述：

  N-叔丁氧羰基-4-哌啶酮 在 四(三苯基膦)钯 sodium carbonate 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 5.33h， 生成 tert-butyl 4-(2,4-dichlorophenyl)-3,6-dihydro-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  Coupling of Arylboronic Acids with a Partially Reduced Pyridine Derivative

  摘要：

  制备了叔丁基碳酰基1,2,3,6-四氢-4-[(三氟甲基)磺酰氧基]吡啶-1-羧酸酯(2)，并将其在钯催化下与多种取代的芳基硼酸3进行偶联反应，生成了一系列叔丁基-4-芳基-1,2,3,6-四氢吡啶-1-羧酸酯4。

  DOI：

  10.1055/s-1991-26626

文献信息

• Design, synthesis, and evaluation of novel aryl-tetrahydropyridine PPARα/γ dual agonists
  作者：Eunkyung Kim、Chan Sun Park、Taedong Han、Myung-Ho Bae、Wonee Chong、Choong Hyun Lee、Young Ah Shin、Byung-Nak Ahn、Mi Kyung Kim、Chang Yell Shin、Moon Ho Son、Jin Kwan Kim、Ho Sang Moon、Hyun Joo Shim、Eun Jung Kim、Soon Hoe Kim、Joong In Lim、Chun Ho Lee

  DOI：10.1016/j.bmcl.2008.08.020

  日期：2008.9

  Aryl-tetrahydropyridine derivatives were prepared and their PPAR alpha/gamma dual agonistic activities were evaluated. Among them, compound (S)-5b was identified as a potent PPAR alpha/gamma dual agonist with an EC50 of 1.73 and 0.64 mu M in hPPAR alpha and gamma, respectively. In diabetic (db/db) mice, compound (S)-5b showed good glucose lowering efficacy and favorable pharmacokinetic properties. (C) 2008 Elsevier Ltd. All rights reserved.
• Coupling of Arylboronic Acids with a Partially Reduced Pyridine Derivative
  作者：David J. Wustrow、Lawrence D. Wise

  DOI：10.1055/s-1991-26626

  日期：——

  tert-Butylcarbonyl 1,2,3,6-tetrahydro-4-[(trifluoromethyl)sulfonyloxy]pyridine-1-carboxylate (2) was prepared and underwent palladium-catalyzed coupling reactions with a variety of substituted arylboronic acids 3 to produce a series of tert-butyl-4-aryl-1,2,3, 6-tetrahydropyridine-1-carboxylates 4.

  制备了叔丁基碳酰基1,2,3,6-四氢-4-[(三氟甲基)磺酰氧基]吡啶-1-羧酸酯(2)，并将其在钯催化下与多种取代的芳基硼酸3进行偶联反应，生成了一系列叔丁基-4-芳基-1,2,3,6-四氢吡啶-1-羧酸酯4。
• 4-Aryl piperazine and piperidine amides as novel mGluR5 positive allosteric modulators
  作者：Hui Xiong、Todd A. Brugel、Michael Balestra、Dean G. Brown、Kelly A. Brush、Caprice Hightower、Lindsay Hinkley、Valerie Hoesch、James Kang、Gerard M. Koether、John P. McCauley、Francis M. McLaren、Laura M. Panko、Thomas R. Simpson、Reed W. Smith、James M. Woods、Becky Brockel、Vijay Chhajlani、Reto A. Gadient、Nathan Spear、Linda A. Sygowski、Minli Zhang、Jalaj Arora、Nathalie Breysse、Julie M. Wilson、Methvin Isaac、Abdelmalik Slassi、Megan M. King

  DOI：10.1016/j.bmcl.2010.10.036

  日期：2010.12

  Positive allosteric modulation of metabotropic glutamate receptor 5 (mGluR5) is regarded as a potential novel treatment for schizophrenic patients. Herein we report the synthesis and SAR of 4-aryl piperazine and piperidine amides as potent mGluR5 positive allosteric modulators (PAMs). Several analogs have excellent activity and desired drug-like properties. Compound 2b was further characterized as a PAM using several in vitro experiments, and produced robust activity in several preclinical animal models. (C) 2010 Elsevier Ltd. All rights reserved.