pentafluorophenyl (R)-trifluoromethyl-methoxy-phenylacetate | 168773-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: pentafluorophenyl (R)-trifluoromethyl-methoxy-phenylacetate
• 英文别名: 2,3,4,5,6-pentafluorophenyl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate；(R)-perfluorophenyl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate；(2,3,4,5,6-pentafluorophenyl) (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 168773-72-6
• 化学式: C₁₆H₈F₈O₃
• 分子量: 400.225
• InChiKey: UGGOVMMOKIUNLP-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (S)-4,5,5-三苯基-2-噁唑烷酮 、 pentafluorophenyl (R)-trifluoromethyl-methoxy-phenylacetate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以34%的产率得到(R,S)-4,5,5-triphenyl-3-(2-methoxy-2-phenyl-2-trifluoromethyl-acetyl)oxazolidin-2-one
  参考文献：
  名称：

  Probing the parallel resolution of Mosher’s acid using a combination of quasi-enantiomeric oxazolidin-2-ones

  摘要：

  Mosher's acid (2-methoxy-2-phenyl-2-trifluoromethylacetic acid) was resolved by parallel resolution of its corresponding pentafluorophenyl active ester using a quasi-enantiomeric combination of oxazolidin-2-ones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.032
• 作为产物：
  描述：

  五氟苯酚 、 (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以92%的产率得到pentafluorophenyl (R)-trifluoromethyl-methoxy-phenylacetate
  参考文献：
  名称：

  Probing the parallel resolution of Mosher’s acid using a combination of quasi-enantiomeric oxazolidin-2-ones

  摘要：

  Mosher's acid (2-methoxy-2-phenyl-2-trifluoromethylacetic acid) was resolved by parallel resolution of its corresponding pentafluorophenyl active ester using a quasi-enantiomeric combination of oxazolidin-2-ones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.032

文献信息

• Selective inhibitors for cyclin-dependent kinases
  申请人：Emory University

  公开号：US08067424B2

  公开（公告）日：2011-11-29

  This invention provides a class of compounds which are useful for specifically inhibiting cyclin-dependent kinases. This class of compounds finds use in treating diseases resulting from inappropriate activity of cyclin-dependent kinases, including cancer, viral infections (e.g., HIV) neurodegenerative disorders (e.g. Alzheimer's disease), and cardiovascular disorders (e.g. atherosclerosis). Moreover, certain members of this class are particularly useful for inhibiting cyclin-dependent kinase 7 and are especially useful for the treatment of breast cancer.

  本发明提供了一类化合物，可用于特异性抑制细胞周期依赖性激酶。这类化合物可用于治疗由于细胞周期依赖性激酶不适当活性引起的疾病，包括癌症、病毒感染（例如，HIV）、神经退行性疾病（例如，阿尔茨海默病）和心血管疾病（例如，动脉粥样硬化）。此外，本类化合物的某些成员特别适用于抑制细胞周期依赖性激酶7，并且特别适用于乳腺癌的治疗。
• Selective Inhibitors for Cyclin-Dependent Kinases
  申请人：Jogalekar Ashutosh S.

  公开号：US20100261683A1

  公开（公告）日：2010-10-14

  This invention provides a class of compounds which are useful for specifically inhibiting cyclin-dependent kinases. This class of compounds finds use in treating diseases resulting from inappropriate activity of cyclin-dependent kinases, including cancer, viral infections (e.g., HIV) neurodegenerative disorders (e.g. Alzheimer's disease), and cardiovascular disorders (e.g. atherosclerosis). Moreover, certain members of this class are particularly useful for inhibiting cyclin-dependent kinase 7 and are especially useful for the treatment of breast cancer.

  本发明提供了一类化合物，可用于特异性抑制细胞周期依赖性激酶。这类化合物可用于治疗由于细胞周期依赖性激酶不适当活动引起的疾病，包括癌症、病毒感染（例如HIV）、神经退行性疾病（例如阿尔茨海默病）和心血管疾病（例如动脉硬化）。此外，该类化合物的某些成员特别适用于抑制细胞周期依赖性激酶7，并且特别适用于治疗乳腺癌。
• Chirospecific Syntheses of Precursors of Cyclopentane and Cyclopentene Carbocyclic Nucleosides by [3 + 3]-Coupling and Transannular Alkylation
  作者：Jeffrey A. Campbell、Won Koo Lee、Henry Rapoport

  DOI：10.1021/jo00119a044

  日期：1995.7

  A new method is reported for the preparation of enantiomerically pure (1R,2S,4S)-1-amino-2-hydroxy-4-(hydroxymethyl)cyclopentane, (1R,2R,4S)-1-amino-2-fluoro-4-(hydroxymethyl)cyclopentane, and (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene, advanced precursors to carbocyclic nucleosides. The method involves initial conversion of D-serine into an aldehyde with 9-phenylfluorenyl protection at nitrogen and O-benzyl protection at oxygen. A [3 + 3]-coupling of this aldehyde with a titanium homoenolate derived from tert-butyl 3-iodopropionate gave the corresponding anti-lactone in high yield. Regioselective hydrogenolysis of the amine protecting group, accompanied by intramolecular O- to N-cyclization formed a lactam. After suitable nitrogen protection and functional group manipulation, transannular alkylation afforded the corresponding 2-benzyl- or 2-(p-methoxybenzyl)-6-hydroxy-2-azabicycclo[2.2.1]-3-heptanone. Functional group modification of the 2-benzyl analogue gave the resulting 6(S)-hydroxy and 6(R)-fluoro N-BOC imides; alternatively, the 2-(p-methoxybenzyl) analogue was converted to an N-BOC imide containing an olefinic Linkage at C-5 and C-6 of the bicycle. Subjecting each of the N-BOC imides to a reduction-deprotection sequence then afforded the desired carbocyclic analogues. The [3 + 3]-coupling method also allowed improved and expedient access to an advanced tribenzylated lactam previously used in the racemic syntheses of the hydroxylated alkaloids D-mannonolactam, deoxymannojirimycin, and prosopinone, providing a formal asymmetric synthesis of these alkaloids.
• US8067424B2
  申请人：——

  公开号：US8067424B2

  公开（公告）日：2011-11-29
• [EN] SELECTIVE INHIBITORS FOR CYCLIN-DEPENDENT KINASES<br/>[FR] INHIBITEURS SÉLECTIFS DES KINASES CYCLINE-DÉPENDANTES
  申请人：UNIV EMORY

  公开号：WO2008151304A1

  公开（公告）日：2008-12-11

  [EN] This invention provides a class of compounds which are useful for specifically inhibiting cyclin-dependent kinases. This class of compounds finds use in treating diseases resulting from inappropriate activity of cyclin-dependent kinases, including cancer, viral infections (e.g., HIV) neurodegenerative disorders (e.g. Alzheimer's disease), and cardiovascular disorders (e.g. atherosclerosis). Moreover, certain members of this class are particularly useful for inhibiting cyclin-dependent kinase 7 and are especially useful for the treatment of breast cancer.
  [FR] La présente invention concerne une catégorie de composés utilisables en vue de l'inhibition sélective des kinases cycline-dépendantes. Cette catégorie de composés est utilisable dans le cadre du traitement de maladies résultant d'une activité peu appropriée des kinases cycline-dépendantes, dont les cancers, les infections virales (par exemple par le VIH), les troubles neurodégénératifs (par exemple la maladie d'Alzheimer) et les affections cardiovasculaires (par exemple l'athérosclérose). En outre, certains membres de cette catégorie peuvent plus particulièrement être utilisés en vue de l'inhibition de la kinase cycline-dépendante 7 et se révèlent tout particulièrement utiles en vue du traitement du cancer du sein.