(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl hydrogen phosphate | 46365-73-5

• 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-trimethylbicyclo[2.2.1]heptan-2-yl hydrogen phosphate
• 英文别名: (-)-bornyl monophosphate；Bornylphosphat；[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] dihydrogen phosphate
• CAS: 46365-73-5；46365-74-6；72581-60-3
• 化学式: C₁₀H₁₉O₄P
• 分子量: 234.232
• InChiKey: UXNCCQNQJBIXFZ-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  冰片 在 四丁基磷酸氢铵 、 三氯乙腈 、 ammonium hydroxide 作用下， 以 乙腈 、 水 为溶剂， 反应 2.0h， 以67%的产率得到(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl hydrogen phosphate
  参考文献：
  名称：

  One-pot synthesis of organophosphate monoesters from alcohols

  摘要：

  A one-pot procedure for the phosphorylation of alcohols provides the corresponding phosphate monoesters in improved yields. The protocol features the use of tetrabutylammonium hydrogen phosphate and trichloroacetonitrile, followed by purification of the crude product by flash chromatography on silica gel. The final step, cation exchange chromatography, affords the organophosphates as ammonium salts that are usually required for biochemical applications. The mechanism appears to be phosphate rather than alcohol activation by trichloroacetonitrile. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.059

文献信息

• Stereochemical disposition of the geminal dimethyl groups in the enzymatic cyclization of geranyl diphosphate to (+)-bornyl diphosphate by recombinant (+)-bornyl diphosphate synthase from Salvia officinalis
  作者：Mitchell L Wise、Hyung-Jung Pyun、Greg Helms、Bryce Assink、Robert M Coates、Rodney B Croteau

  DOI：10.1016/s0040-4020(01)00451-3

  日期：2001.6

  Regiospecifically deuterated geranyl diphosphate, in concert with NMR spectrometry, was employed to demonstrate that the trans-methyl group (C8) of geranyl diphosphate becomes the C9 carbon of (+)-bornyl diphosphate (geminal methyl syn to the diphosphate moiety) and that the cis-methyl group (C9) becomes the C8 (geminal methyl anti to the diphosphate). The syntheses of the relevant substrates and products, with accompanying spectrometric data are provided. (C) 2001 Elsevier Science Ltd. All rights reserved.