(+)-pentafluorophenyl 2-(6-methoxy-naphthalen-2-yl)propionate | 872989-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+)-pentafluorophenyl 2-(6-methoxy-naphthalen-2-yl)propionate
• 英文别名: pentafluorophenyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate；pentafluorophenyl (S)-2-(6-methoxynaphthalen-2-yl)propionate；naproxen pentafluorophenyl ester；(2,3,4,5,6-pentafluorophenyl) (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
• CAS: 872989-08-7
• 化学式: C₂₀H₁₃F₅O₃
• 分子量: 396.313
• InChiKey: KDNMHEPRTPRGLY-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+)-pentafluorophenyl 2-(6-methoxy-naphthalen-2-yl)propionate 、 2-噁唑烷酮,4-(1-甲基乙基)- 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以69%的产率得到
  参考文献：
  名称：

  Efficient Parallel Resolution of Racemic Evans’ Oxazolidinones Usingquasi-Enantiomeric Profens

  摘要：

  借助准对映异构体的普罗芬组合，实现了消旋的埃文斯恶唑啉酮的高效拆分。立体控制水平很高，得到了构型可预测的产物。

  DOI：

  10.1055/s-2005-922784
• 作为产物：
  描述：

  五氟苯酚 、 萘普生 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(+)-pentafluorophenyl 2-(6-methoxy-naphthalen-2-yl)propionate
  参考文献：
  名称：

  Efficient Parallel Resolution of Racemic Evans’ Oxazolidinones Usingquasi-Enantiomeric Profens

  摘要：

  借助准对映异构体的普罗芬组合，实现了消旋的埃文斯恶唑啉酮的高效拆分。立体控制水平很高，得到了构型可预测的产物。

  DOI：

  10.1055/s-2005-922784

文献信息

• Oligonucleotides comprising a non-phosphate backbone linkage
  申请人：Manoharan Muthiah

  公开号：US20060287260A1

  公开（公告）日：2006-12-21

  One aspect of the present invention relates to a ribonucleoside substituted with a phosphonamidite group at the 3′-position. In certain embodiments, the phosphonamidite is an alkyl phosphonamidite. Another aspect of the present invention relates to a double-stranded oligonucleotide comprising at least one non-phosphate linkage. Representative non-phosphate linkages include phosphonate, hydroxylamine, hydroxylhydrazinyl, amide, and carbamate linkages. In certain embodiments, the non-phosphate linkage is a phosphonate linkage. In certain embodiments, a non-phosphate linkage occurs in only one strand. In certain embodiments, a non-phosphate linkage occurs in both strands. In certain embodiments, a ligand is bound to one of the oligonucleotide strands comprising the double-stranded oligonucleotide. In certain embodiments, a ligand is bound to both of the oligonucleotide strands comprising the double-stranded oligonucleotide. In certain embodiments, the oligonucleotide strands comprise at least one modified sugar moiety. Another aspect of the present invention relates to a single-stranded oligonucleotide comprising at least one non-phosphate linkage. Representative non-phosphate linkages include phosphonate, hydroxylamine, hydroxylhydrazinyl, amide, and carbamate linkages. In certain embodiments, the non-phosphate linkage is a phosphonate linkage. In certain embodiments, a ligand is bound to the oligonucleotide strand. In certain embodiments, the oligonucleotide comprises at least one modified sugar moiety.

  本发明的一个方面涉及在3'-位置用磷酰胺基团取代的核糖核苷。在某些实施例中，磷酰胺基团是烷基磷酰胺基团。本发明的另一个方面涉及包含至少一个非磷酸酯连接的双链寡核苷酸。代表性的非磷酸酯连接包括磷酸酯、羟胺、羟基肼基、酰胺和碳酸酯连接。在某些实施例中，非磷酸酯连接是磷酸酯连接。在某些实施例中，非磷酸酯连接仅出现在一条链中。在某些实施例中，非磷酸酯连接出现在两条链中。在某些实施例中，配体结合到包含双链寡核苷酸的寡核苷酸链中的一条链上。在某些实施例中，配体结合到包含双链寡核苷酸的寡核苷酸链中的两条链上。在某些实施例中，寡核苷酸链包含至少一个修饰的糖基团。本发明的另一个方面涉及包含至少一个非磷酸酯连接的单链寡核苷酸。代表性的非磷酸酯连接包括磷酸酯、羟胺、羟基肼基、酰胺和碳酸酯连接。在某些实施例中，非磷酸酯连接是磷酸酯连接。在某些实施例中，配体结合到寡核苷酸链上。在某些实施例中，寡核苷酸包含至少一个修饰的糖基团。
• Resolution of Pentafluorophenyl Active Esters Using (S)-4-Phenyloxazolidin-2-thione
  作者：Jason Eames、Najla Al Shaye、Tom Broughton、Elliot Coulbeck

  DOI：10.1055/s-0028-1088218

  日期：2009.4

  A series of structurally related racemic pentafluorophenyl active esters were resolved using an equimolar amount of (S)-4-phenyloxazolidin-2-thione. The levels of diastereocontrol were found to be excellent (>86% de at ˜30% conversion).

  使用等摩尔量的(S)-4-苯基恶唑啉-2-硫酮解析了一系列结构相关的外消旋五氟苯基活性酯。结果表明，非对映控制水平非常出色（转化率 Ë30%时de>86%）。
• Desymmetrisation of (4R,5S)-4,5-diphenylimidazolidine-2-thione using pentafluorophenyl active esters
  作者：Anna Andreou、Jason Eames、Majid Motevalli、Timothy J. Prior、Michael Watkinson

  DOI：10.1016/j.tetlet.2010.01.019

  日期：2010.3

  (4R,5S)-4,5-Diphenylimidazolidine-2-thione is efficiently desymmetrised by stereorandom deprotonation with NaHMDS, followed by kinetic resolution of the resulting racemic intermediate with an enantiomerically pure pentafluorophenyl active ester. The levels of diastereocontrol were found to be excellent (86-92% de at similar to 30% conversion). This desymmetrisation reaction is an example of a masked resolution. (C) 2010 Elsevier Ltd. All rights reserved.

  (4R,5S)-4,5-二苯基亚氨基硫脲在NaHMDS作用下发生无序去质子化反应，随后通过使用对映体纯的五氟苯基活性酯对生成的外消旋中间体进行动力学拆分。实验发现，双相控制水平极为出色（在约30%转化率时，对映体过量率可达86%-92%）。这一不对称反应是“假性拆分”的一个实例。© 2010 Elsevier Ltd. 保留所有权利。
• Resolution of (4RS,5RS)-4,5-diphenylimidazolidine-2-thione using pentafluorophenyl active esters
  作者：Anna Andreou、Najla Al Shaye、Hannah Brown、Jason Eames

  DOI：10.1016/j.tetlet.2010.10.157

  日期：2010.12

  (4RS,5RS)-4,5-Diphenylimidazolidine-2-thione is resolved efficiently by treatment with NaHMDS and an enantiomerically pure pentafluorophenyl active ester. The levels of diastereocontrol were excellent (up to 90% de). (C) 2010 Elsevier Ltd. All rights reserved.

  (4RS,5RS)-4,5-二苯基咪达灵-2-硫酮在经过NaHMDS和光学纯的五氟苯基活性酯处理后，得以高效拆分。对映异构控制的水平非常出色（高达90% de）。版权© 2010爱思唯尔有限公司，版权所有。
• Modified iRNA agents
  申请人：Manoharan Muthiah

  公开号：US20050107325A1

  公开（公告）日：2005-05-19

  The invention relates to iRNA agents, which preferably include a monomer in which the ribose moiety has been replaced by a moiety other than ribose. The inclusion of such a monomer can allow for modulation of a property of the iRNA agent into which it is incorporated, e.g., by using the non-ribose moiety as a point to which a ligand or other entity, e.g., a lipophilic moiety. e.g., cholesterol, is is directly, or indirectly, tethered. The invention also relates to methods of making and using such modified iRNA agents.

  本发明涉及iRNA（干扰RNA）代理，其中最好包括一个单体，其中核糖基团被替换为核糖外的基团。包括这样的单体可以允许调节iRNA代理的某个性质，例如，通过使用非核糖基团作为配体或其他实体（例如，亲脂性基团，如胆固醇）的点来直接或间接地连接。本发明还涉及制备和使用这样的修饰iRNA代理的方法。