dimethyl (2E,6E)-1-hydroxy-3,7,11-trimethyl-2,6,10-dodecatrienylphosphonate | 149190-70-5

• 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: dimethyl (2E,6E)-1-hydroxy-3,7,11-trimethyl-2,6,10-dodecatrienylphosphonate
• 英文别名: Dimethyl [1-hydroxy-(E,E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]phosphonate；(2E,6E)-1-dimethoxyphosphoryl-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
• CAS: 149190-70-5
• 化学式: C₁₇H₃₁O₄P
• 分子量: 330.404
• InChiKey: KDSPPBVUYZZBGG-NWFDBUFXSA-N

物化性质

• 沸点：
  438.5±45.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl (2E,6E)-1-hydroxy-3,7,11-trimethyl-2,6,10-dodecatrienylphosphonate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以60%的产率得到dimethyl (2E,6E)-3,7,11-trimethyl-1-oxo-2,6,10-dodecatrienylphosphonate
  参考文献：
  名称：

  一种有效的C = X化合物膦化方法

  摘要：

  在胺和苯胺​​氢卤化物存在下，研究了亚磷酸三烷基酯与C = X亲电试剂（醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化烯烃）的反应。我们发现吡啶氢卤化物有效地激活了亚磷酸三烷基酯与各种C = X亲电试剂的反应：醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化的烯烃。特别高的活性显示出吡啶氢碘化物。该反应是合成羟基膦酸酯，氨基膦酸酯，氨基甲酰基膦酸酯，氨基甲酰基硫代膦酸酯和亚甲基双膦酸酯的便利方法。

  DOI：

  10.1134/s1070363210040055
• 作为产物：
  描述：

  Farnesal 、 三甲氧基磷 在 吡啶溴化氢盐 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到dimethyl (2E,6E)-1-hydroxy-3,7,11-trimethyl-2,6,10-dodecatrienylphosphonate
  参考文献：
  名称：

  一种有效的C = X化合物膦化方法

  摘要：

  在胺和苯胺​​氢卤化物存在下，研究了亚磷酸三烷基酯与C = X亲电试剂（醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化烯烃）的反应。我们发现吡啶氢卤化物有效地激活了亚磷酸三烷基酯与各种C = X亲电试剂的反应：醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化的烯烃。特别高的活性显示出吡啶氢碘化物。该反应是合成羟基膦酸酯，氨基膦酸酯，氨基甲酰基膦酸酯，氨基甲酰基硫代膦酸酯和亚甲基双膦酸酯的便利方法。

  DOI：

  10.1134/s1070363210040055

文献信息

• Farnesyl pyrophosphate analogs
  申请人：Merck & Co., Inc.

  公开号：US05298655A1

  公开（公告）日：1994-03-29

  The present invention is directed to farnesyl pyrophosphate analogs which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention, and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.

  本发明涉及抑制法尼基蛋白转移酶（FTase）和致癌基因蛋白Ras的法尼基焦磷酸酯类似物。该发明还涉及含有本发明化合物的化疗组合物，以及抑制法尼基蛋白转移酶和致癌基因蛋白Ras的方法。
• Synthesis of Nonracemic Dimethyl α-(Hydroxyfarnesyl)phosphonates via Oxidation of Dimethyl Farnesylphosphonate with (Camphorsulfonyl)oxaziridines
  作者：Diana M. Cermak、Yanming Du、David F. Wiemer

  DOI：10.1021/jo980984z

  日期：1999.1.1

  Several strategies for synthesis of nonracemic dimethyl alpha-(hydroxyfarnesyl)phosphonate and the parent phosphonic acid have been explored. Separation of diastereomeric derivatives prepared by esterification of racemic a-hydroxy phosphonate with (S)-(+)-O-methylmandelic acid was possible, and these diastereomers could be assigned absolute stereochemistry on the basis of literature precedent; However, hydrolysis to the alpha-hydroxy phosphonic acid was accompanied by extensive isomerization. Addition of a nonracemic phosphonamidite to farnesal also gave nonracemic material, but again hydrolysis was problematic. Oxidation of dimethyl farnesylphosphonate anion with nonracemic (camphorsulfonyl)oxaziridines was shown to be regio- and stereoselective for formation of the a-hydroxy phosphonate. Enantiomeric excess of similar to 70% ee was established by conversion of the oxidation products to their (S)-(+)-O-methylmandelate derivatives. Although hydrolysis of these methyl esters was accompanied by extensive racemization, both enantiomers of alpha-(hydroxyfarnesyl)phosphonic acid were obtained in low ee by this strategy.
• Synthesis of isoprenyl bis(phosphonates)
  作者：O. O. Kolodyazhnaya、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363209040306

  日期：2009.4
• An efficient method for the phosphonation of C=X compounds
  作者：A. O. Kolodyazhnaya、O. O. Kolodyazhnaya、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363210040055

  日期：2010.4

  (aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates, isothiocyanates, and activated olefins) in the presence of amines and anilines hydrohalides was studied. We found that pyridine hydrohalides effectively activate the reaction of tralkyl phosphites with various C=X electrophiles: aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates, isothiocyanates, and activated

  在胺和苯胺​​氢卤化物存在下，研究了亚磷酸三烷基酯与C = X亲电试剂（醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化烯烃）的反应。我们发现吡啶氢卤化物有效地激活了亚磷酸三烷基酯与各种C = X亲电试剂的反应：醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化的烯烃。特别高的活性显示出吡啶氢碘化物。该反应是合成羟基膦酸酯，氨基膦酸酯，氨基甲酰基膦酸酯，氨基甲酰基硫代膦酸酯和亚甲基双膦酸酯的便利方法。