{(2S)-2-{双[3,5-双(三氟甲基)苯基]羟甲基}-1-吡咯烷基[4-(1-吡咯烷基)-3-吡啶基]甲酮 | 951008-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: {(2S)-2-{双[3,5-双(三氟甲基)苯基]羟甲基}-1-吡咯烷基[4-(1-吡咯烷基)-3-吡啶基]甲酮
• 中文别名: {(2)-2-{双[3,5-双(三氟甲基)苯基]羟甲基}-1-吡咯烷基[4-(1-吡咯烷基)-3-吡啶基]甲酮
• 英文名称: ((2S)-2-(bis(3,5-bis(trifluoromethyl)phenyl)hydroxymethyl)-1-pyrrolidinyl)(4-(1-pyrrolidinyl)-3-pyridinyl)methanone
• 英文别名: {(2S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}-1-pyrrolidinyl}[4-(1-pyrrolidinyl)-3-pyridinyl]methanone；[(2S)-2-[bis[3,5-bis(trifluoromethyl)phenyl]-hydroxymethyl]pyrrolidin-1-yl]-(4-pyrrolidin-1-ylpyridin-3-yl)methanone
• CAS: 951008-65-4
• 化学式: C₃₁H₂₅F₁₂N₃O₂
• 分子量: 699.539
• InChiKey: LVJPWYSGCCTYAC-VWLOTQADSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  575.8±50.0 °C(Predicted)
• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  48
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  16

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  (S)-proline-N-carboxyanhydride 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 {(2S)-2-{双[3,5-双(三氟甲基)苯基]羟甲基}-1-吡咯烷基[4-(1-吡咯烷基)-3-吡啶基]甲酮
  参考文献：
  名称：

  Nonenzymatic Acylative Kinetic Resolution of Baylis−Hillman Adducts

  摘要：

  The first efficient nonenzymatic acylative kinetic resolution of Baylis-Hillman adducts is reported. Chiral pyridine catalyst 1a and an optimized analogue 1e are capable of promoting the synthetically useful enantioselective acylation (the efficiency of which is outstanding for sp(2)-sp(2) carbinol substrates, s = 3.5-13.1, ee up to 97%) of Baylis-Hillman adducts derived from recalcitrant precursors which are currently difficult to synthesize utilizing benchmark asymmetric Baylis-Hillman reaction catalyst technology. A novel one-pot synthesis-kinetic resolution process involving a DBU-catalyzed Baylis-Hillman reaction and subsequent 1e/DBU-mediated enantioselective acylation has also been developed.

  DOI：

  10.1021/jo071223b
• 作为试剂：
  描述：

  5-苯基四氮唑 、 乙醛 、 焦碳酸二乙酯 在 {(2S)-2-{双[3,5-双(三氟甲基)苯基]羟甲基}-1-吡咯烷基[4-(1-吡咯烷基)-3-吡啶基]甲酮 作用下， 以 乙醚 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  路易斯碱催化动态动力学拆分区域选择性和对映选择性合成唑半胺酯

  摘要：

  我们报告了一种模块化的三组分动态动力学分辨率 (DKR)，它提供了源自唑类和醛类的富含对映异构体的半胺醛酯。通过封端（例如，酰化）平衡的唑醛加合物，该新颖且可扩展的反应可用于以区域选择性方式合成有价值的取代唑。使用脯氨醇衍生的 DMAP 催化剂作为手性路易斯碱，可以获得高化学产率和高对映体过量的产物。DKR 以数公斤规模进行，为一个领先的临床候选药物生产四唑前药片段，这带来了巨大的合成挑战。

  DOI：

  10.1021/jacs.6b00207

文献信息

• SUBSTITUTED AMIDE COMPOUNDS
  申请人：Pfizer Inc.

  公开号：US20140315928A1

  公开（公告）日：2014-10-23

  The present invention is directed at substituted amide compounds, pharmaceutical compositions containing such compounds and the use of such compounds to reduce plasma lipid levels, such as LDL-cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases, in mammals, including humans.

  本发明涉及替代酰胺化合物，含有这种化合物的药物组合物以及利用这种化合物降低血浆脂质水平，如LDL-胆固醇和甘油三酯，并据此治疗由高水平的LDL-胆固醇和甘油三酯加重的疾病，如动脉粥样硬化和心血管疾病，在哺乳动物，包括人类中的应用。
• N-PIPERIDIN-3-YLBENZAMIDE DERIVATIVES FOR TREATING CARDIOVASCULAR DISEASES
  申请人：Pfizer Inc.

  公开号：EP2986599A1

  公开（公告）日：2016-02-24
• US9227956B2
  申请人：——

  公开号：US9227956B2

  公开（公告）日：2016-01-05
• [EN] N-PIPERIDIN-3-YLBENZAMIDE DERIVATIVES FOR TREATING CARDIOVASCULAR DISEASES<br/>[FR] DÉRIVÉS DE N-PIPÉRIDIN-3-YLBENZAMIDE DANS LE TRAITEMENT DES MALADIES CARDIOVASCULAIRES
  申请人：PFIZER

  公开号：WO2014170786A1

  公开（公告）日：2014-10-23

  The present invention is directed at substituted amide compounds of formula (I), pharmaceutical compositions containing such compounds and the use of such compounds to reduce plasma lipid levels, such as LDL- cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases, in mammals, including humans.
• Nonenzymatic Acylative Kinetic Resolution of Baylis−Hillman Adducts
  作者：Ciarán Ó Dálaigh、Stephen J. Connon

  DOI：10.1021/jo071223b

  日期：2007.8.31

  The first efficient nonenzymatic acylative kinetic resolution of Baylis-Hillman adducts is reported. Chiral pyridine catalyst 1a and an optimized analogue 1e are capable of promoting the synthetically useful enantioselective acylation (the efficiency of which is outstanding for sp(2)-sp(2) carbinol substrates, s = 3.5-13.1, ee up to 97%) of Baylis-Hillman adducts derived from recalcitrant precursors which are currently difficult to synthesize utilizing benchmark asymmetric Baylis-Hillman reaction catalyst technology. A novel one-pot synthesis-kinetic resolution process involving a DBU-catalyzed Baylis-Hillman reaction and subsequent 1e/DBU-mediated enantioselective acylation has also been developed.