(R/S)-4-hydroxymethyl-4-[2-(4-octylphenyl)ethyl]oxazolidin-2-one | 847672-61-1

• 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: (R/S)-4-hydroxymethyl-4-[2-(4-octylphenyl)ethyl]oxazolidin-2-one
• 英文别名: (R/S)-4-hydroxymethyl-4-[2-(4-octyl-phenyl)-ethyl]-oxazolidin-2-one；4-(hydroxymethyl)-4-[2-(4-octylphenyl)ethyl]-1,3-oxazolidin-2-one
• CAS: 847672-61-1
• 化学式: C₂₀H₃₁NO₃
• 分子量: 333.471
• InChiKey: PPWVIJUOPWCELF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R/S)-4-hydroxymethyl-4-[2-(4-octylphenyl)ethyl]oxazolidin-2-one 在 palladium on activated charcoal 四氮唑 、 lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 45.0h， 生成 S) FTY720磷酸酯
  参考文献：
  名称：

  Novel Immunomodulator FTY720 Is Phosphorylated in Rats and Humans To Form a Single Stereoisomer. Identification, Chemical Proof, and Biological Characterization of the Biologically Active Species and Its Enantiomer

  摘要：

  In vivo phosphorylation. of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1. Starting from the prochiral amino alcohol 1, racemic and enantiomerically pure phosphates of 1 were synthesized. Pure enantiomers were obtained after purification of a partially protected key intermediate on an enantioselective support. The absolute stereochemistry was determined by X-ray diffraction.

  DOI：

  10.1021/jm050242f
• 作为产物：
  描述：

  氯甲酸苄酯 、 2-氨基-2-[2-(4-辛基苯基)乙基]-1,3-丙二醇 在 sodium hydroxide 作用下， 反应 48.0h， 生成 (R/S)-4-hydroxymethyl-4-[2-(4-octylphenyl)ethyl]oxazolidin-2-one
  参考文献：
  名称：

  Novel Immunomodulator FTY720 Is Phosphorylated in Rats and Humans To Form a Single Stereoisomer. Identification, Chemical Proof, and Biological Characterization of the Biologically Active Species and Its Enantiomer

  摘要：

  In vivo phosphorylation. of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1. Starting from the prochiral amino alcohol 1, racemic and enantiomerically pure phosphates of 1 were synthesized. Pure enantiomers were obtained after purification of a partially protected key intermediate on an enantioselective support. The absolute stereochemistry was determined by X-ray diffraction.

  DOI：

  10.1021/jm050242f

文献信息

• [EN] AMINOPROPANOL DERIVATIVES<br/>[FR] DERIVES D'AMINOPROPANOL
  申请人：NOVARTIS AG

  公开号：WO2005021503A1

  公开（公告）日：2005-03-10

  Compounds of formula (I): wherein R1, R2, n and m are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.

  式（I）的化合物：其中R1、R2、n和m如规范中定义，它们的生产过程，它们的用途以及含有它们的药物组合物。
• Aminopropanol derivatives
  申请人：Albert Rainer

  公开号：US20060264403A1

  公开（公告）日：2006-11-23

  Compounds of formula I: wherein R 1 , R 2 , n and m are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.

  式I的化合物：其中R1、R2、n和m如规范中定义，它们的制备方法，它们的用途以及包含它们的药物组合物。
• FTY720 HALOGENATED DERIVATIVES
  申请人：Auberson Yves

  公开号：US20120244071A1

  公开（公告）日：2012-09-27

  There are provided new iodo- and bromo-compounds, and their use as diagnostic agents and imaging agents for diseases and disorders wherein S1P receptor expression is altered.

  提供了新的碘和溴化合物，并将其用作诊断剂和成像剂，用于表达S1P受体发生改变的疾病和疾病的诊断和成像。
• AMINOPROPANOL DERIVATIVES
  申请人：ALBERT Rainer

  公开号：US20120277194A1

  公开（公告）日：2012-11-01

  Compounds of formula I: wherein R 1 , R 2 , n and m are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.

  公式I的化合物：其中R1、R2、n和m如规范中定义，其生产过程，其用途以及包含它们的制药组合物。
• Novel Immunomodulator FTY720 Is Phosphorylated in Rats and Humans To Form a Single Stereoisomer. Identification, Chemical Proof, and Biological Characterization of the Biologically Active Species and Its Enantiomer
  作者：Rainer Albert、Klaus Hinterding、Volker Brinkmann、Danilo Guerini、Constanze Müller-Hartwieg、Helmut Knecht、Corinne Simeon、Markus Streiff、Trixie Wagner、Karl Welzenbach、Frédéric Zécri、Markus Zollinger、Nigel Cooke、Eric Francotte

  DOI：10.1021/jm050242f

  日期：2005.8.1

  In vivo phosphorylation. of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1. Starting from the prochiral amino alcohol 1, racemic and enantiomerically pure phosphates of 1 were synthesized. Pure enantiomers were obtained after purification of a partially protected key intermediate on an enantioselective support. The absolute stereochemistry was determined by X-ray diffraction.