(S)-(-)-5-Chloro-2-methoxy-α-fluoro-α-[2-nitro-4-(trifluoromethyl)phenyl]benzeneacetic acid | 206194-02-7

• 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: (S)-(-)-5-Chloro-2-methoxy-α-fluoro-α-[2-nitro-4-(trifluoromethyl)phenyl]benzeneacetic acid
• 英文别名: (alphaS)-alpha-Fluoro-alpha-(2-methoxy-5-chlorophenyl)-2-nitro-4-(trifluoromethyl)benzeneacetic acid；(2S)-2-(5-chloro-2-methoxyphenyl)-2-fluoro-2-[2-nitro-4-(trifluoromethyl)phenyl]acetic acid
• CAS: 206194-02-7
• 化学式: C₁₆H₁₀ClF₄NO₅
• 分子量: 407.706
• InChiKey: JGGUUELZNXQODQ-HNNXBMFYSA-N

物化性质

• 沸点：
  488.2±45.0 °C(Predicted)
• 密度：
  1.523±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-(-)-5-Chloro-2-methoxy-α-fluoro-α-[2-nitro-4-(trifluoromethyl)phenyl]benzeneacetic acid 在 盐酸 、 sodium dithionite 作用下， 生成 (3R)-3-(5-氯-2-甲氧基苯基)-3-氟-6-(三氟甲基)-1H-吲哚-2-酮
  参考文献：
  名称：

  The synthesis and characterization of BMS-204352 (MaxiPost™) and related 3-fluorooxindoles as openers of maxi-K potassium channels

  摘要：

  3-Aryl-3-fluorooxindoles can be efficiently synthesized in two steps by the addition of an aryl Grignard to an isatin, followed by treatment with DAST. Oxindole 1 (BMS-204352; MaxiPost(TM)) can be isolated using chiral HPLC or prepared by employing chiral resolution. Cloned maxi-K channels are opened by 1, which demonstrates a brain/plasma ratio > 9 in rats. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00101-4
• 作为产物：
  描述：

  (5-氯-2-甲氧基苯基)乙酸甲酯 在 (S)-(-)- α-甲基苄胺 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-(-)-5-Chloro-2-methoxy-α-fluoro-α-[2-nitro-4-(trifluoromethyl)phenyl]benzeneacetic acid
  参考文献：
  名称：

  The synthesis and characterization of BMS-204352 (MaxiPost™) and related 3-fluorooxindoles as openers of maxi-K potassium channels

  摘要：

  3-Aryl-3-fluorooxindoles can be efficiently synthesized in two steps by the addition of an aryl Grignard to an isatin, followed by treatment with DAST. Oxindole 1 (BMS-204352; MaxiPost(TM)) can be isolated using chiral HPLC or prepared by employing chiral resolution. Cloned maxi-K channels are opened by 1, which demonstrates a brain/plasma ratio > 9 in rats. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00101-4

文献信息

• Preparation of 3-fluoro oxindole derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US05892106A1

  公开（公告）日：1999-04-06

  The present invention relates to novel intermediates of the formula ##STR1## wherein the wavy bond () represents the racemate, the (R)-enantiomer or the (S)-enantiomer; and R is hydrogen, a carboxyl-protecting group or a cation of an addition salt; or solvate thereof; and to the use thereof in a process for the preparation of certain 3-fluoro oxindole derivatives.

  本发明涉及一种新的中间体，其化学式为##STR1##其中波浪线()表示外消旋体，(R)-对映体或(S)-对映体; R代表氢，羧基保护基或加成盐阳离子; 或其溶剂化物; 以及其在制备特定的3-氟氧吲哚衍生物的过程中的应用。
• PREPARATION OF 3-FLUORO OXINDOLE DERIVATIVES
  申请人：Bristol-Myers Squibb Company

  公开号：EP0946173B1

  公开（公告）日：2005-05-18
• US5808095A
  申请人：——

  公开号：US5808095A

  公开（公告）日：1998-09-15
• US5892106A
  申请人：——

  公开号：US5892106A

  公开（公告）日：1999-04-06
• The synthesis and characterization of BMS-204352 (MaxiPost™) and related 3-fluorooxindoles as openers of maxi-K potassium channels
  作者：Piyasena Hewawasam、Valentin K. Gribkoff、Yadagiri Pendri、Steven I. Dworetzky、Nicholas A. Meanwell、Eduardo Martinez、Christopher G. Boissard、Debra J. Post-Munson、Joanne T. Trojnacki、Krishnaswamy Yeleswaram、Lorraine M. Pajor、Jay Knipe、Qi Gao、Robert Perrone、John E. Starrett

  DOI：10.1016/s0960-894x(02)00101-4

  日期：2002.4

  3-Aryl-3-fluorooxindoles can be efficiently synthesized in two steps by the addition of an aryl Grignard to an isatin, followed by treatment with DAST. Oxindole 1 (BMS-204352; MaxiPost(TM)) can be isolated using chiral HPLC or prepared by employing chiral resolution. Cloned maxi-K channels are opened by 1, which demonstrates a brain/plasma ratio > 9 in rats. (C) 2002 Elsevier Science Ltd, All rights reserved.