2-(3-Benzyloxycarbonylamino-propyl)-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester | 681456-90-6

• 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-(3-Benzyloxycarbonylamino-propyl)-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester
• 英文别名: Methyl 1-[(4-methoxyphenyl)methyl]-2-[3-(phenylmethoxycarbonylamino)propyl]azetidine-2-carboxylate
• CAS: 681456-90-6
• 化学式: C₂₄H₃₀N₂O₅
• 分子量: 426.513
• InChiKey: FYMSCPCTJDINOA-UHFFFAOYSA-N

物化性质

• 沸点：
  555.6±50.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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-Benzyloxycarbonylamino-propyl)-1-(4-methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester 在 palladium dihydroxide 、 palladium on activated charcoal 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 tris(triphenylphosphine)rhodium(I) carbonyl hydride 二苯基硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以89%的产率得到2-(3-Benzyloxycarbonylamino-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