2-(3-tert-Butoxycarbonylamino-propyl)-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester | 681456-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-tert-Butoxycarbonylamino-propyl)-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester
• 英文别名: Methyl 1-[(4-methoxyphenyl)methyl]-2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]azetidine-2-carboxylate
• CAS: 681456-82-6
• 化学式: C₂₁H₃₂N₂O₅
• 分子量: 392.495
• InChiKey: FNQPFLSUAYTKDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-tert-Butoxycarbonylamino-propyl)-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid methyl 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， 生成 2-(3-tert-Butoxycarbonylamino-propyl)-azetidine-2-carboxylic acid methyl 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：

  2-(3-Benzyloxycarbonylamino-propyl)-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid methyl ester 在 palladium on activated charcoal 、 tris(triphenylphosphine)rhodium(I) carbonyl hydride 二苯基硅烷 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 生成 2-(3-tert-Butoxycarbonylamino-propyl)-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester
  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