trans-2-Benzyl-3,4-dimethylisoxazolidin-5-one | 863115-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: trans-2-Benzyl-3,4-dimethylisoxazolidin-5-one
• 英文别名: (3S,4S)-2-benzyl-3,4-dimethyl-1,2-oxazolidin-5-one
• CAS: 863115-39-3
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: PBGOPDVEJUQQKF-UWVGGRQHSA-N

物化性质

• 沸点：
  292.6±33.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-2-Benzyl-3,4-dimethylisoxazolidin-5-one 在 palladium on carbon 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 生成 (2S,3S)-3-amino-2-methyl butyric acid
  参考文献：
  名称：

  Discovery of a stable macrocyclic o-aminobenzamide Hsp90 inhibitor which significantly decreases tumor volume in a mouse xenograft model

  摘要：

  An extension of our previously reported series of macrocyclic ortho-aminobenzamide Hsp90 inhibitors is reported. Addition of a second methyl group to the tether provided analogs that show increased potency in binding as well as cell-proliferation assays and, more importantly, are stable toward microsomes. We wish to disclose the discovery of a macrocycle which showed impressive biomarker activity 24-h post dosing and which demonstrated prolonged exposure in tumors. When studied in a lung cancer xenograft model, the compound demonstrated significant tumor size reduction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.102
• 作为产物：
  描述：

  (E)-2-甲基-2-丁烯酰氯 在 C₂₇H₂₈N₂O₂ 正丁基锂 、 magnesium(II) perchlorate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 trans-2-Benzyl-3,4-dimethylisoxazolidin-5-one
  参考文献：
  名称：

  BETA-AMINO ACIDS AND METHODS AND INTERMEDIATES FOR MAKING SAME

  摘要：

  披露了未在β位取代的β-氨基酸；在β位用芳基取代的β-氨基酸；在α位用芳基取代的β-氨基酸；在α位带有两个取代基的β-氨基酸；和/或在α和β位用与α和β位的碳原子一起形成环的基团取代的β-氨基酸。还披露了制备上述β-氨基酸和其他β-氨基酸的方法，包括提供α，β-不饱和亚胺；将α，β-不饱和亚胺转化为2-取代异噁唑啉-5-酮；将2-取代异噁唑啉-5-酮转化为β-氨基酸。

  公开号：

  US20110218342A1

文献信息

• US8034974B2
  申请人：——

  公开号：US8034974B2

  公开（公告）日：2011-10-11
• BETA-AMINO ACIDS AND METHODS AND INTERMEDIATES FOR MAKING SAME
  申请人：Sibi Mukund P.

  公开号：US20110218342A1

  公开（公告）日：2011-09-08

  Disclosed are β-amino acids that are unsubstituted in the β position; that are substituted in the β position with an aryl group; that are substituted in the α position with an aryl group; that bear two substituents in the α position; and/or that are substituted in the α and β positions with groups which, together with the carbon atoms at the α and β positions, form a ring. Also disclosed are methods for making the above-mentioned β-amino acids and other β-amino acids which involve providing an α,β-unsaturated imide; converting the α,β-unsaturated imide to a 2-substituted-isoxazolidin-5-one; and converting the 2-substituted-isoxazolidin-5-one to a β-amino acid.

  披露了未在β位取代的β-氨基酸；在β位用芳基取代的β-氨基酸；在α位用芳基取代的β-氨基酸；在α位带有两个取代基的β-氨基酸；和/或在α和β位用与α和β位的碳原子一起形成环的基团取代的β-氨基酸。还披露了制备上述β-氨基酸和其他β-氨基酸的方法，包括提供α，β-不饱和亚胺；将α，β-不饱和亚胺转化为2-取代异噁唑啉-5-酮；将2-取代异噁唑啉-5-酮转化为β-氨基酸。
• Discovery of a stable macrocyclic o-aminobenzamide Hsp90 inhibitor which significantly decreases tumor volume in a mouse xenograft model
  作者：Christoph W. Zapf、Jonathan D. Bloom、Zhong Li、Russell G. Dushin、Thomas Nittoli、Mercy Otteng、Antonia Nikitenko、Jennifer M. Golas、Hao Liu、Judy Lucas、Frank Boschelli、Erik Vogan、Andrea Olland、Mark Johnson、Jeremy I. Levin

  DOI：10.1016/j.bmcl.2011.05.102

  日期：2011.8

  An extension of our previously reported series of macrocyclic ortho-aminobenzamide Hsp90 inhibitors is reported. Addition of a second methyl group to the tether provided analogs that show increased potency in binding as well as cell-proliferation assays and, more importantly, are stable toward microsomes. We wish to disclose the discovery of a macrocycle which showed impressive biomarker activity 24-h post dosing and which demonstrated prolonged exposure in tumors. When studied in a lung cancer xenograft model, the compound demonstrated significant tumor size reduction. (C) 2011 Elsevier Ltd. All rights reserved.