{(1R,2S)-2-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-cyclopropyl}-phosphonic acid diethyl ester | 873332-06-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: {(1R,2S)-2-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-cyclopropyl}-phosphonic acid diethyl ester
• CAS: 873332-06-0
• 化学式: C₁₇H₂₅N₂O₄P
• 分子量: 352.37
• InChiKey: XUHXOVLSROCNIK-VVLHAWIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  91.58
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {(1R,2S)-2-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-cyclopropyl}-phosphonic acid diethyl ester 在 lead(IV) acetate 、 盐酸 、 Dowex 1X₈-200 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 以46%的产率得到(2S,1'S,2'R)-2-(2'-phosphonocyclopropyl)glycine
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of (2S,1′R,2′S)- and (2S,1′S,2′R)-2-(2′-phosphonocyclopropyl)glycines, two novel conformationally constrained l-AP4 analogues

  摘要：

  Two novel constrained L-AP4 analogues, (2S,1'R,2'S)- and (2S,1'S,2R)-2-(2'-phosphonocyclopropyl)glycines (7) and (8), were synthesized and evaluated as mGluR ligands. Compound 7 showed to be a group III mGluRs agonist with micromolar activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.014
• 作为产物：
  描述：

  trans-diethyl 2-(hydroxymethyl)cyclopropylphosphonate 在 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 {(1R,2S)-2-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-cyclopropyl}-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of (2S,1′R,2′S)- and (2S,1′S,2′R)-2-(2′-phosphonocyclopropyl)glycines, two novel conformationally constrained l-AP4 analogues

  摘要：

  Two novel constrained L-AP4 analogues, (2S,1'R,2'S)- and (2S,1'S,2R)-2-(2'-phosphonocyclopropyl)glycines (7) and (8), were synthesized and evaluated as mGluR ligands. Compound 7 showed to be a group III mGluRs agonist with micromolar activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.014