ethyl (1S,2S,1'S)-2-methyl-1-(1'-methyl-2-phenylethylamino)cyclopropanephosphonate

• 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: ethyl (1S,2S,1'S)-2-methyl-1-(1'-methyl-2-phenylethylamino)cyclopropanephosphonate
• 英文别名: ethoxy-[(1S,2S)-2-methyl-1-[[(2S)-1-phenylpropan-2-yl]amino]cyclopropyl]phosphinic acid
• 化学式: C₁₅H₂₄NO₃P
• 分子量: 297.334
• InChiKey: ADZAHNDQLPPPIK-YDHLFZDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  去甲麻黄碱 在 palladium dihydroxide 三甲基氯硅烷 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 20.0~55.0 ℃ 、101.33 kPa 条件下， 反应 94.08h， 生成 ethyl (1S,2S,1'S)-2-methyl-1-(1'-methyl-2-phenylethylamino)cyclopropanephosphonate
  参考文献：
  名称：

  Preparation of enantiomerically pure (1S,2S)-1-aminocyclopropanephosphonic acid from methylcyclopropanone acetal via spirophosphonate intermediates

  摘要：

  An easy and efficient one-pot reaction from readily available methylcyclopropanone acetal (2S)-4b gave the spirophosphonates 8a-b with excellent diastereoselectivity. These phosphonates, after catalytic hydrogenolysis and hydrolysis, furnished the enantiomerically pure (1S,2S)-1-amino-2-methylcyclopropanephosphonic acid 3b (analogue of (1R,2S)-allo-norcoronamic acid). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00134-8

文献信息

• Preparation of enantiomerically pure (1S,2S)-1-aminocyclopropanephosphonic acid from methylcyclopropanone acetal via spirophosphonate intermediates
  作者：Antoine Fadel、Nicolas Tesson

  DOI：10.1016/s0957-4166(00)00134-8

  日期：2000.5

  An easy and efficient one-pot reaction from readily available methylcyclopropanone acetal (2S)-4b gave the spirophosphonates 8a-b with excellent diastereoselectivity. These phosphonates, after catalytic hydrogenolysis and hydrolysis, furnished the enantiomerically pure (1S,2S)-1-amino-2-methylcyclopropanephosphonic acid 3b (analogue of (1R,2S)-allo-norcoronamic acid). (C) 2000 Elsevier Science Ltd. All rights reserved.