(R,S)-N-(tert-butyloxycarbonyl)-α-n-propylbenzylamine | 1034110-31-0

• 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: (R,S)-N-(tert-butyloxycarbonyl)-α-n-propylbenzylamine
• 英文别名: tert-butyl N-(1-phenylbutyl)carbamate
• CAS: 1034110-31-0
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: NCSDLGOZWQILAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R,S)-N-(tert-butyloxycarbonyl)-α-n-propylbenzylamine 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.0h， 以1.06 g的产率得到1-(phenyl)butylamine hydrochloride
  参考文献：
  名称：

  3-(2-Aminocarbonylphenyl)propanoic acid analogs as potent and selective EP3 receptor antagonists. Part 1: Discovery and exploration of the carboxyamide side chain

  摘要：

  A series of 3-(2-aminocarbonyl-4-phenoxymethylphenyl) propanoic acid analogs were synthesized and evaluated for their EP3 antagonist activity in the presence of additive serum albumin. Several compounds were biologically evaluated for their in vivo efficacy with respect to the PGE(2)-induced uterine contraction in pregnant rats as well as their pharmacokinetics. The discovery process of these potent and selective EP3 antagonists and their structure activity relationship are also presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.023
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1-苯基丁胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以73%的产率得到(R,S)-N-(tert-butyloxycarbonyl)-α-n-propylbenzylamine
  参考文献：
  名称：

  New C5-Alkylated Indolobenzazepinones Acting as Inhibitors of Tubulin Polymerization: Cytotoxic and Antitumor Activities

  摘要：

  A series of 5-alkylindolobenzazepin-7-ones was synthesized by Suzuki coupling between 3-iodoindole-2-carboxylates and the appropriate alpha-alkylbenzylamino o-boronic acids followed by cyclization to the lactam. Derivatives having a linear alkyl chain at C5 were found to be highly cytotoxic to KB cells with IC50 values in the 30-80 nM range. These compounds also inhibited the polymerization of tubulin with IC50's of 1-2 mu M. Compound 4f ((S)-5-ethyl) showed comparable antiproliferative activities (IC50's of 30-70 nM) in a variety of cancer cell lines, cell growth being arrested at the G2/M phase. Compound 4f induced apoptosis in a dose-dependent manner in three different cancer cell lines and was shown to affect cell morphology in a manner consistent with its inhibitory action on tubulin polymerization. Using the experimental model of glioma grafted on the chick chorio-allantoic membrane, local treatment with compound 4f markedly reduced tumor progression.

  DOI：

  10.1021/jm701466p

文献信息

• A PROCESS FOR PREPARING (2R,3S)-1,2-EPOXY-3-(PROTECTED)AMINO-4-SUBSTITUTED BUTANE AND INTERMEDIATES THEREOF
  申请人：Bristol-Myers Squibb Company

  公开号：EP1893765A1

  公开（公告）日：2008-03-05
• [EN] A PROCESS FOR PREPARING (2R,3S)-1,2-EPOXY-3-(PROTECTED)AMINO-4-SUBSTITUTED BUTANE AND INTERMEDIATES THEREOF<br/>[FR] PROCEDE POUR PREPARER DU BUTANE (2R,3S)-1,2-EPOXY-3-(PROTEGE)AMINO-4-SUBSTITUE ET DES INTERMEDIAIRES DE CELUI-CI
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2006127180A1

  公开（公告）日：2006-11-30

  [EN] The present invention relates to a process for preparing (2R,3S)-1-halo-2-hydroxy-3-(protected)amino-4-substituted butane comprising contacting a mutagenized Rhodococcus erythropolis having ATCC deposit no. PTA-6648 with (3S)-1-halo-2-oxo-3-(protected)amino-4-substituted butane substrate. The present invention also relates to a process comprising mixing (2R,3S)-1-halo-2-hydroxy-3-(protected)amino-4-substituted butane with at least one base in the presence of at least one solvent to produce a reaction mixture containing (2R,3S)-1,2-epoxy-3-(protected)amino-4-substituted butane. The present invention further relates to a process comprising crystallizing the (2R,3S)-1,2-epoxy-3-(protected)amino-4-substituted butane out of the reaction mixture by concurrently adding water and the reaction mixture together. The present invention is also directed to a mutagenized Rhodococcus erythropolis having ATCC deposit no. PTA-6648.
  [FR] La présente invention concerne un procédé pour préparer du butane (2R,3S)-1-halo-2-hydroxy-3-(protégé)amino-4-substitué, comprenant la mise en contact d'un Rhodococcus erythropolis mutagénisé ayant un dépôt ATCC no. PTA-6648 avec un substrat de butane (3S)-1-halo-2-oxo-3-(protégé)amino-4-substituté. L'invention a également pour objet un procédé comprenant le mélange de butane (2R,3S)-1-halo-2-hydroxy-3-(protégé)amino-4-substituté avec au moins une base, en la présence d'au moins un solvant, pour produire un mélange réactionnel contenant du butane (2R,3S)-1,2-époxy-3-(protégé)amino-4-substituté. L'invention concerne aussi un procédé comprenant la cristallisation du butane (2R,3S)-1,2-époxy-3-(protégé)amino-4-substituté, hors du mélange réactionnel, par adjonction simultanée d'eau et du mélange réactionnel. L'invention se rapporte également à un Rhodococcus erythropolis mutagénisé ayant un dépôt ATCC no. PTA-6648.