2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol | 1453852-02-2

• 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: 2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol
• 英文别名: 2-(Tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol；2-[tert-butyl(dimethyl)silyl]oxy-1-(4-chloro-3-fluorophenyl)ethanol
• CAS: 1453852-02-2
• 化学式: C₁₄H₂₂ClFO₂Si
• 分子量: 304.864
• InChiKey: KTBITCVLPAOFPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol 在 potassium tert-butylate 、 四丁基碘化铵 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 仲丁醇 为溶剂， 反应 46.17h， 生成 1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-6-methyl-4-(2-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-4-yl)pyridin-2(1H)-one
  参考文献：
  名称：

  Discovery of Highly Potent, Selective, and Efficacious Small Molecule Inhibitors of ERK1/2

  摘要：

  Using structure-based design, a novel series of pyridone ERK1/2 inhibitors was developed. Optimization led to the identification of (S)-14k, a potent, selective, and orally bioavailable agent that inhibited tumor growth in mouse xenograft models. On the basis of its in vivo efficacy and preliminary safety profiles, (S)-14k was selected for further preclinical evaluation.

  DOI：

  10.1021/jm501921k
• 作为产物：
  描述：

  magnesium,1-chloro-2-fluorobenzene-4-ide,bromide 、 叔丁基二甲基硅氧烷基乙醛 在 ice 、 水 、 乙酸乙酯 、 氯化铵 、 crude product 、 hexanes EtOAc 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以to give 2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol (2.92 g, 9.58 mmol, 92.8% yield) as an oil的产率得到2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol
  参考文献：
  名称：

  SERINE/THREONINE KINASE INHIBITORS

  摘要：

  提供了化学式I或其立体异构体、互变异构体、前药或药物可接受的盐的化合物，其可用于治疗过度增殖、疼痛和炎症性疾病。公开了使用化学式I或其立体异构体、互变异构体、前药或药物可接受的盐的化合物，用于哺乳动物细胞中的体外、体内和原位诊断、预防或治疗此类疾病或相关病理条件的方法。

  公开号：

  US20140249127A1

文献信息

• [EN] SERINE/THREONINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA SÉRINE / THRÉONINE KINASE
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2013130976A1

  公开（公告）日：2013-09-06

  Compounds of Formula I or a stereoisomer, tautomer, prodrug or pharmaceutically acceptable salt thereof are provided, which are useful for the treatment of hyperproliferative, pain and inflammatory diseases. Methods of using compounds of Formula I or a stereoisomer, tautomer, prodrug or pharmaceutically acceptable salt thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  提供了公式I或其立体异构体、互变异构体、前药或药用盐，这些化合物可用于治疗高增殖、疼痛和炎症性疾病。公开了使用公式I或其立体异构体、互变异构体、前药或药用盐在哺乳动物细胞中进行体外、体内和体内诊断、预防或治疗这些疾病或相关病理状况的方法。
• Serine/threonine kinase inhibitors
  申请人：Array BioPharma Inc.

  公开号：US08697715B2

  公开（公告）日：2014-04-15

  Compounds of Formula I or a stereoisomer, tautomer, prodrug or pharmaceutically acceptable salt thereof are provided, which are useful for the treatment of hyperproliferative, pain and inflammatory diseases. Methods of using compounds of Formula I or a stereoisomer, tautomer, prodrug or pharmaceutically acceptable salt thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  提供了公式I的化合物或其立体异构体、互变异构体、前药或药学上可接受的盐，用于治疗过度增殖、疼痛和炎症性疾病。本文还揭示了使用公式I的化合物或其立体异构体、互变异构体、前药或药学上可接受的盐的方法，用于哺乳动物细胞中的体外、体内和原位诊断、预防或治疗此类疾病或相关病理条件。
• SERINE/THREONINE KINASE INHIBITORS
  申请人：ARRAY BIOPHARMA INC.

  公开号：US20130252934A1

  公开（公告）日：2013-09-26

  Compounds of Formula I or a stereoisomer, tautomer, prodrug or pharmaceutically acceptable salt thereof are provided, which are useful for the treatment of hyperproliferative, pain and inflammatory diseases. Methods of using compounds of Formula I or a stereoisomer, tautomer, prodrug or pharmaceutically acceptable salt thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  提供了化学式I或其立体异构体、互变异构体、前药或药学上可接受的盐的化合物，用于治疗高增殖、疼痛和炎症性疾病。揭示了使用化学式I或其立体异构体、互变异构体、前药或药学上可接受的盐的化合物，在哺乳动物细胞中进行体外、体内和原位诊断、预防或治疗这些疾病或相关病理条件的方法。
• Discovery of Highly Potent, Selective, and Efficacious Small Molecule Inhibitors of ERK1/2
  作者：Li Ren、Jonas Grina、David Moreno、James F. Blake、John J. Gaudino、Rustam Garrey、Andrew T. Metcalf、Michael Burkard、Matthew Martinson、Kevin Rasor、Huifen Chen、Brian Dean、Stephen E. Gould、Patricia Pacheco、Sheerin Shahidi-Latham、Jianping Yin、Kristina West、Weiru Wang、John G. Moffat、Jacob B. Schwarz

  DOI：10.1021/jm501921k

  日期：2015.2.26

  Using structure-based design, a novel series of pyridone ERK1/2 inhibitors was developed. Optimization led to the identification of (S)-14k, a potent, selective, and orally bioavailable agent that inhibited tumor growth in mouse xenograft models. On the basis of its in vivo efficacy and preliminary safety profiles, (S)-14k was selected for further preclinical evaluation.