[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-bromo-4-diethoxyphosphoryl-4,4-difluorobutanoate | 191534-28-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-bromo-4-diethoxyphosphoryl-4,4-difluorobutanoate
• CAS: 191534-28-8
• 化学式: C₁₈H₃₀BrF₂O₅P
• 分子量: 475.308
• InChiKey: SCMWQTAYONFNTP-XDSKCHBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-bromo-4-diethoxyphosphoryl-4,4-difluorobutanoate 在 sodium azide 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以65%的产率得到[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-azido-4-diethoxyphosphoryl-4,4-difluorobutanoate
  参考文献：
  名称：

  A new method for the synthesis of a phosphonic acid analogue of phosphoserine via a novel 1,1-difluorophosphonate intermediate

  摘要：

  The synthesis of [4,4-difluoro-4-(dihydroxyphosphinyl)-2-amino] butanoic acid, an analogue of phosphoserine, is reported by two different routes; one route gave a racemic mixture, and the other, by using the strategy of a coupling reaction with a chiral compound, gave a single enantiomer.

  DOI：

  10.1016/s0022-1139(96)03516-6
• 作为产物：
  描述：

  bromozinc(1+),1-[difluoromethyl(ethoxy)phosphoryl]oxyethane 在 4-二甲氨基吡啶 、 copper(l) iodide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 101.0h， 生成 [(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-bromo-4-diethoxyphosphoryl-4,4-difluorobutanoate
  参考文献：
  名称：

  A new method for the synthesis of a phosphonic acid analogue of phosphoserine via a novel 1,1-difluorophosphonate intermediate

  摘要：

  The synthesis of [4,4-difluoro-4-(dihydroxyphosphinyl)-2-amino] butanoic acid, an analogue of phosphoserine, is reported by two different routes; one route gave a racemic mixture, and the other, by using the strategy of a coupling reaction with a chiral compound, gave a single enantiomer.

  DOI：

  10.1016/s0022-1139(96)03516-6

文献信息

• A new method for the synthesis of a phosphonic acid analogue of phosphoserine via a novel 1,1-difluorophosphonate intermediate
  作者：A.M. Kawamoto、M.M. Campbell

  DOI：10.1016/s0022-1139(96)03516-6

  日期：1997.3

  The synthesis of [4,4-difluoro-4-(dihydroxyphosphinyl)-2-amino] butanoic acid, an analogue of phosphoserine, is reported by two different routes; one route gave a racemic mixture, and the other, by using the strategy of a coupling reaction with a chiral compound, gave a single enantiomer.