diethyl (+)-(1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexan-1-ylphosphonate | 1253573-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: diethyl (+)-(1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexan-1-ylphosphonate
• 英文别名: (1S,5R)-1-diethoxyphosphoryl-3-oxabicyclo[3.1.0]hexan-2-one
• CAS: 1253573-46-4
• 化学式: C₉H₁₅O₅P
• 分子量: 234.189
• InChiKey: WYIQJSUVRMZQOL-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (+)-(1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexan-1-ylphosphonate 、 乙酸酐 在 氨 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以90%的产率得到(+)-(1S,2R)-2-carbamoyl-2-(diethoxyphosphoryl)cyclopropylmethyl acetate
  参考文献：
  名称：

  An efficient approach to the synthesis of enantiomerically pure trans-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids

  摘要：

  The synthesis of (1R,2S)- and (1S,2R)-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids was accomplished using different strategies. The (1R,2S)-stereoisomer could be efficiently obtained by the cyclopropanation of ethyl diethoxyphosphorylacetate with the cyclic sulfate derived from (S)-3-benzyloxy-1,2-propandiol as a key step. The (1S,2R)-stereoisomer was synthesized from a readily available (1S,5R)-3-oxabicyclo[3.1.0]hexan-2-on-1-phosphonate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.017
• 作为产物：
  描述：

  diethyl (+)-(1S,2R)-2-(hydroxymethyl)-1-((R)-1-phenylethylcarbamoyl)cyclopropylphosphonate 在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以85%的产率得到diethyl (+)-(1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexan-1-ylphosphonate
  参考文献：
  名称：

  An efficient approach to the synthesis of enantiomerically pure trans-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids

  摘要：

  The synthesis of (1R,2S)- and (1S,2R)-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids was accomplished using different strategies. The (1R,2S)-stereoisomer could be efficiently obtained by the cyclopropanation of ethyl diethoxyphosphorylacetate with the cyclic sulfate derived from (S)-3-benzyloxy-1,2-propandiol as a key step. The (1S,2R)-stereoisomer was synthesized from a readily available (1S,5R)-3-oxabicyclo[3.1.0]hexan-2-on-1-phosphonate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.017

文献信息

• An efficient approach to the synthesis of enantiomerically pure trans-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids
  作者：Katarzyna Wąsek、Jacek Kędzia、Henryk Krawczyk

  DOI：10.1016/j.tetasy.2010.07.017

  日期：2010.9

  The synthesis of (1R,2S)- and (1S,2R)-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids was accomplished using different strategies. The (1R,2S)-stereoisomer could be efficiently obtained by the cyclopropanation of ethyl diethoxyphosphorylacetate with the cyclic sulfate derived from (S)-3-benzyloxy-1,2-propandiol as a key step. The (1S,2R)-stereoisomer was synthesized from a readily available (1S,5R)-3-oxabicyclo[3.1.0]hexan-2-on-1-phosphonate. (C) 2010 Elsevier Ltd. All rights reserved.