2-Benzyl-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid tert-butyl ester | 681456-86-0

• 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: 2-Benzyl-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 2-benzyl-1-[(4-methoxyphenyl)methyl]azetidine-2-carboxylate；tert-butyl 2-benzyl-1-[(4-methoxyphenyl)methyl]azetidine-2-carboxylate
• CAS: 681456-86-0
• 化学式: C₂₃H₂₉NO₃
• 分子量: 367.488
• InChiKey: QNMXAJWKCHFXJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Benzyl-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid tert-butyl ester 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、275.8 kPa 条件下， 反应 15.0h， 以78%的产率得到2-Benzyl-azetidine-2-carboxylic acid tert-butyl ester; hydrochloride
  参考文献：
  名称：

  Simple access to novel azetidine-containing conformationally restricted amino acids by chemoselective reduction of β-lactams

  摘要：

  Reduction with diphenylsilane and catalytic amounts of tris(triphenylphosphine)rhodium(I) carbonyl hydride resulted in an efficient, chemoselective method for the transformation of amino-acid-derived beta-lactams into the corresponding azetidines, which after removal of the p-methoxybenzyl group, afforded a new family of conformationally restricted amino acids. Phe-derived compounds were obtained in enantiopure form by combining HPLC resolution of the beta-lactam precursor and the above-mentioned procedure. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.023
• 作为产物：
  描述：

  4-benzyl-1-(4-methoxy)benzyl-4-tert-butoxycarbonyl-2-azetidinone 在 二苯基硅烷 作用下， 生成 2-Benzyl-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and anti-HCMV activity of 1-acyl-β-lactams and 1-acylazetidines derived from phenylalanine

  摘要：

  Different Phe-derived 1-acyl-beta-lactams, analogous to a series of 2-azetidinones acting as HCMV serine protease inhibitors, were synthesized. Some of these compounds were modest inhibitors of the HCMV replication. Interestingly, removal of the carbonyl group of the beta-lactam ring, most likely acting as the serine trap, resulted in an azetidine derivative with anti-HCMV activity comparable to that of the reference compound ganciclovir. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.010