2-phenyl-4-(1-(S)-benzyloxycarbonylamino-ethyl)-1H-imidazole | 269085-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-4-(1-(S)-benzyloxycarbonylamino-ethyl)-1H-imidazole
• 英文别名: benzyl N-[(1S)-1-(2-phenyl-1H-imidazol-4-yl)ethyl]carbamate；benzyl N-[(1S)-1-(2-phenyl-1H-imidazol-5-yl)ethyl]carbamate
• CAS: 269085-40-7
• 化学式: C₁₉H₁₉N₃O₂
• 分子量: 321.379
• InChiKey: QEYKRMBIIXPNHU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(1-(S)-benzyloxycarbonylamino-ethyl)-1H-imidazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到2-phenyl-4-(1-(S)-aminoethyl)-1H-imidazole
  参考文献：
  名称：

  Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids

  摘要：

  A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available N-protected alpha-amino acids, as the source of chirality, which are converted into appropriate alpha-diazoketones and, consequently, into alpha-bromoketones. These alpha-bromoketones are good precursors for reactions with amidines to provide the imidazole ring. The deprotection into the final products was carried out using hydrogen. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.049
• 作为产物：
  描述：

  benzyl (S)-(4-diazo-3-oxobutan-2-yl)carbamate 在 ammonium acetate 、 二甲基二环氧乙烷 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.17h， 生成 2-phenyl-4-(1-(S)-benzyloxycarbonylamino-ethyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis of amino acid-derived imidazoles from enantiopure N-protected α-amino glyoxals

  摘要：

  A range of novel imidazoles, including three histidine derivatives, with chiral side chains derived from amino acids and dipeptides have been synthesised from N-Cbz-protected alpha-amino glyoxals. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02267-4

文献信息

• Synthesis of amino acid-derived imidazoles from enantiopure N-protected α-amino glyoxals
  作者：Michelle Groarke、M.Anthony McKervey、Mark Nieuwenhuyzen

  DOI：10.1016/s0040-4039(99)02267-4

  日期：2000.2

  A range of novel imidazoles, including three histidine derivatives, with chiral side chains derived from amino acids and dipeptides have been synthesised from N-Cbz-protected alpha-amino glyoxals. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids
  作者：Filip Bureš、Jiří Kulhánek

  DOI：10.1016/j.tetasy.2005.01.049

  日期：2005.4

  A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available N-protected alpha-amino acids, as the source of chirality, which are converted into appropriate alpha-diazoketones and, consequently, into alpha-bromoketones. These alpha-bromoketones are good precursors for reactions with amidines to provide the imidazole ring. The deprotection into the final products was carried out using hydrogen. (c) 2005 Elsevier Ltd. All rights reserved.