(1S,2R)-2-(dibenzylamino)-1-(4-fluorophenyl)-3-methylbutan-1-ol | 937275-49-5

• 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: (1S,2R)-2-(dibenzylamino)-1-(4-fluorophenyl)-3-methylbutan-1-ol
• CAS: 937275-49-5
• 化学式: C₂₅H₂₈FNO
• 分子量: 377.502
• InChiKey: DKGNFPSIYLYDKS-RPBOFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-(dibenzylamino)-1-(4-fluorophenyl)-3-methylbutan-1-ol 在 盐酸 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 氯化亚砜 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (2S,3R)-2-(4-fluorophenyl)-3-isopropylaziridine
  参考文献：
  名称：

  Synthesis and in vitro characterization of platinum(II) anticancer coordinates using FTIR spectroscopy and NCI COMPARE: A fast method for new compound discovery

  摘要：

  Platinum-based drugs have been used for several decades to treat various cancers successfully. Cisplatin is the original compound in this class; it cross-links DNA, resulting in cell cycle arrest and cell death via apoptosis. Cisplatin is effective against several tumor types but exhibits toxic side effects; in addition, tumors often develop resistance. An original in vitro approach is proposed to determine whether platinum-based research compounds are good candidates for further study by comparing them to marketed drugs using FTIR spectroscopy and the COMPARE analysis from the NCI. Both methods can produce fingerprints and highlight differences between the compounds, classifying the candidates and revealing promising derivatives. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.017
• 作为产物：
  描述：

  (R)-benzyl 2-(dibenzylamino)-3-methylbutanoate 在 lithium aluminium tetrahydride 、 草酰氯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.75h， 生成 (1S,2R)-2-(dibenzylamino)-1-(4-fluorophenyl)-3-methylbutan-1-ol 、 (1R,2R)-2-(dibenzylamino)-1-(4-fluorophenyl)-3-methylbutan-1-ol
  参考文献：
  名称：

  Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds

  摘要：

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.079

文献信息

• Synthesis and in vitro characterization of platinum(II) anticancer coordinates using FTIR spectroscopy and NCI COMPARE: A fast method for new compound discovery
  作者：Gilles Berger、Hélène Leclercqz、Allison Derenne、Michel Gelbcke、Erik Goormaghtigh、Jean Nève、Véronique Mathieu、François Dufrasne

  DOI：10.1016/j.bmc.2014.04.017

  日期：2014.7

  Platinum-based drugs have been used for several decades to treat various cancers successfully. Cisplatin is the original compound in this class; it cross-links DNA, resulting in cell cycle arrest and cell death via apoptosis. Cisplatin is effective against several tumor types but exhibits toxic side effects; in addition, tumors often develop resistance. An original in vitro approach is proposed to determine whether platinum-based research compounds are good candidates for further study by comparing them to marketed drugs using FTIR spectroscopy and the COMPARE analysis from the NCI. Both methods can produce fingerprints and highlight differences between the compounds, classifying the candidates and revealing promising derivatives. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds
  作者：Gilles Berger、Michel Gelbcke、Emilie Cauët、Michel Luhmer、Jean Nève、François Dufrasne

  DOI：10.1016/j.tetlet.2012.11.079

  日期：2013.2

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.