[(1S,2S)-2-[diethoxyphosphoryl(difluoro)methyl]cyclopropyl]methanol | 194546-52-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: [(1S,2S)-2-[diethoxyphosphoryl(difluoro)methyl]cyclopropyl]methanol
• CAS: 194546-52-6
• 化学式: C₉H₁₇F₂O₄P
• 分子量: 258.202
• InChiKey: RSVVLNHQAURKLG-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1S,2S)-2-[diethoxyphosphoryl(difluoro)methyl]cyclopropyl]methanol 在 甲醇 、 三甲基溴硅烷 、 potassium carbonate 、 三乙胺 作用下， 以 盐酸 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 (2'S,3'S)-9-(4'-phosphono-4',4'-difluoro-2',3'-methanobutyl)guanine
  参考文献：
  名称：

  Synthesis of (2′S,3′S)-9-(4′-phosphono-4′,4′-difluoro-2′,3′-methanobutyl)guanine and its enantiomer. Evaluation of the inhibitory activity for purine nucleoside phosphorylase

  摘要：

  Conformationally constrained analogues 2a and ent-2a of 9-(difluorophosphonopentyl)guanines 1, a multi-substrate analogue inhibitor of PNP, were prepared from optically active trans-1-(diethoxyphosphinyl)difluromethy-2-hydroxymethylcyclopropanes (+)-6 and (-)-6, Enzymatic double resolution was applied to obtain (+)-6 and (-)-6 with high enantiomeric purity. Inhibitory activity of 2a and ent-2a were found to be 2400-fold less potent than 1. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00704-7

文献信息

• Convenient Synthesis of Cyclopropylalkanol Derivatives Possessing a Difluoromethylenephosphonate Group at the Ring
  作者：Tsutomu Yokomatsu、Hiroshi Abe、Takehiro Yamagishi、Kenji Suemune、Shiroshi Shibuya

  DOI：10.1021/jo990922o

  日期：1999.10.1
• Synthesis of (2′S,3′S)-9-(4′-phosphono-4′,4′-difluoro-2′,3′-methanobutyl)guanine and its enantiomer. Evaluation of the inhibitory activity for purine nucleoside phosphorylase
  作者：Tsutomu Yokomatsu、Mutsumi Sato、Hiroshi Abe、Kenji Suemune、Keita Matsumoto、Taro Kihara、Shinji Soeda、Hiroshi Shimeno、Shiroshi Shibuya

  DOI：10.1016/s0040-4020(97)00704-7

  日期：1997.8

  Conformationally constrained analogues 2a and ent-2a of 9-(difluorophosphonopentyl)guanines 1, a multi-substrate analogue inhibitor of PNP, were prepared from optically active trans-1-(diethoxyphosphinyl)difluromethy-2-hydroxymethylcyclopropanes (+)-6 and (-)-6, Enzymatic double resolution was applied to obtain (+)-6 and (-)-6 with high enantiomeric purity. Inhibitory activity of 2a and ent-2a were found to be 2400-fold less potent than 1. (C) 1997 Elsevier Science Ltd.