(R)-methyl 1-(4-methoxybenzyl)-2-benzylazetidine-2-carboxylate | 681456-98-4

• 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)-methyl 1-(4-methoxybenzyl)-2-benzylazetidine-2-carboxylate
• 英文别名: methyl (2R)-2-benzyl-1-[(4-methoxyphenyl)methyl]azetidine-2-carboxylate
• CAS: 681456-98-4
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: IYOGDYZQUGBORJ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (R)-methyl 1-(4-methoxybenzyl)-2-benzylazetidine-2-carboxylate 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 (R)-2-Benzyl-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：

  methyl (2R)-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 (R)-methyl 1-(4-methoxybenzyl)-2-benzylazetidine-2-carboxylate
  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

文献信息

• Stereochemical Diversity in Asymmetric Cyclization via Memory of Chirality
  作者：Takeo Kawabata、Seiji Matsuda、Shimpei Kawakami、Daiki Monguchi、Katsuhiko Moriyama

  DOI：10.1021/ja0670761

  日期：2006.12.1

  potassium amide bases in DMF, cyclization proceeds with retention of configuration, while inversion of configuration was observed with lithium amide bases in THF. Chirality of the parent amino acids was preserved during enolate formation and cyclization to give aza-cyclic amino acids in up to 98% ee with retention of configuration or inversion of configuration, depending on the reaction conditions. Thus, both

  已开发出 N-Boc-N-ω-溴烷基-α-氨基酸衍生物的对映发散不对称环化。在 DMF 中使用氨基钾碱时，环化在构型保留的情况下进行，而在 THF 中使用氨基化锂碱时观察到构型反转。在烯醇化物形成和环化过程中保留了母体氨基酸的手性，以产生高达 98% ee 的氮杂环氨基酸，并保留构型或反转构型，这取决于反应条件。因此，具有四取代立体中心的环状氨基酸的两种对映异构体均以高对映异构纯度从容易获得的l-α-氨基酸制备。该协议也适用于α-氨基酸衍生物的螺环化和分子内共轭添加，
• 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.