methyl (2S)-2-benzyl-1-[(4-methoxyphenyl)methyl]-4-oxoazetidine-2-carboxylate | 610314-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: methyl (2S)-2-benzyl-1-[(4-methoxyphenyl)methyl]-4-oxoazetidine-2-carboxylate
• CAS: 610314-28-8
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: OIWBYSOLNJHAEL-FQEVSTJZSA-N

物化性质

• 沸点：
  512.5±50.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-benzyl-1-[(4-methoxyphenyl)methyl]-4-oxoazetidine-2-carboxylate 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， 生成 (S)-2-Benzyl-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
• 作为产物：
  描述：

  D-苯丙氨酸甲酯 在 sodium tetrahydroborate 、 (4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇 、 (叔丁基亚氨基)三(吡咯烷)膦 、 methyloxirane 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 methyl (2S)-2-benzyl-1-[(4-methoxyphenyl)methyl]-4-oxoazetidine-2-carboxylate
  参考文献：
  名称：

  β-Lactams derived from phenylalanine and homologues: effects of the distance between the aromatic rings and the α-stereogenic reactive center on the memory of chirality

  摘要：

  The enantioselectivity in the base-promoted cyclization of N-chloroacetyl derivatives of Phe, Phg, and Hph is dependent on the side-chain length, with the best results for Phg analogues (up to 74% ee). In contrast, shortening of the N-substituent, from a (p-methoxy)benzyl group to a (p-methoxy)phenyl moiety, led to a decrease in selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.057

文献信息

• Stereoselective synthesis of amino acid-derived β-lactams. Experimental evidence for TADDOL as a memory of chirality enhancer
  作者：M. Angeles Bonache、Pilar López、Mercedes Martín-Martínez、M. Teresa García-López、Carlos Cativiela、Rosario González-Muñiz

  DOI：10.1016/j.tet.2005.09.125

  日期：2006.1

  In model experiments, concerning the modulation of memory of chirality during the intramolecular alkylation of N-(Pmethoxy)benzyl-N-chloroacetyl-Phe-O'Bu derivative to the corresponding beta-lactam, TADDOL was selected from a panel of different phase-transfer catalysts as the best chiral additive (ee up to 82%). We have demonstrated here that the degree and sign of the cyclization selectivity was virtually independent on TADDOL configuration, providing experimental proof that in this reaction this additive works as a memory of chirality enhancer and not as a real catalyst. The effect of TADDOL is strongly dependent on the starting amino acid derivative, the increase of selectivity being only observed for those with aromatic side chains. (c) 2005 Elsevier Ltd. All rights reserved.
• β-Lactams derived from phenylalanine and homologues: effects of the distance between the aromatic rings and the α-stereogenic reactive center on the memory of chirality
  作者：M. Angeles Bonache、Carlos Cativiela、M. Teresa García-López、Rosario González-Muñiz

  DOI：10.1016/j.tetlet.2006.06.057

  日期：2006.8

  The enantioselectivity in the base-promoted cyclization of N-chloroacetyl derivatives of Phe, Phg, and Hph is dependent on the side-chain length, with the best results for Phg analogues (up to 74% ee). In contrast, shortening of the N-substituent, from a (p-methoxy)benzyl group to a (p-methoxy)phenyl moiety, led to a decrease in selectivity. (c) 2006 Elsevier Ltd. All rights reserved.
• Simple access to novel azetidine-containing conformationally restricted amino acids by chemoselective reduction of β-lactams
  作者：Guillermo Gerona-Navarro、Ma Angeles Bonache、Miriam Alı́as、Ma Jesús Pérez de Vega、Ma Teresa Garcı́a-López、Pilar López、Carlos Cativiela、Rosario González-Muñiz

  DOI：10.1016/j.tetlet.2004.01.023

  日期：2004.3

  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.