phenyl bis(trimethylsilyl) phosphite | 137862-40-9

• 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: phenyl bis(trimethylsilyl) phosphite
• CAS: 137862-40-9
• 化学式: C₁₂H₂₃O₃PSi₂
• 分子量: 302.458
• InChiKey: PRJRLRUXESTFTA-UHFFFAOYSA-N

物化性质

• 沸点：
  83 °C(Press: 0.1 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl bis(trimethylsilyl) phosphite 、 棕榈酰氯 在 甲醇 作用下， 反应 2.0h， 以11.5%的产率得到[1-hydroxy-1-(hydroxy-phenoxy-phosphoryl)hexadecyl]-phosphonic acid monophenyl ester
  参考文献：
  名称：

  双膦酸型萃取剂对一系列稀土金属离子具有极高的萃取能力

  摘要：

  合成了一种双膦酸型萃取剂，并用于研究对稀土金属的萃取行为。新试剂对这些离子表现出极高的提取能力。这种能力还伴随着萃取剂进入水相的低泄漏，这反映了试剂的疏水性和部分未解离的膦酸基团的存在。

  DOI：

  10.1007/s10847-019-00927-5
• 作为产物：
  描述：

  亚磷酸二苯酯 在 ammonium hydroxide 作用下， 反应 4.0h， 生成 phenyl bis(trimethylsilyl) phosphite
  参考文献：
  名称：

  双膦酸酯前药：合成新的芳香族和脂肪族1-羟基-1,1-双膦酸酯偏酯

  摘要：

  开发了各种1-羟基-1,1-双膦酸酯偏酯的制备方法。它们是从（烷基或苯基）双（三甲基甲硅烷基）亚磷酸酯和芳族或脂族酰氯得到的，然后进行甲醇分解。

  DOI：

  10.1016/j.tet.2005.05.053

文献信息

• Syntheses of Phosphonic Esters of Alendronate, Pamidronate and Neridronate
  作者：Erwann Guénin、Maelle Monteil、Nadia Bouchemal、Thierry Prangé、Marc Lecouvey

  DOI：10.1002/ejoc.200601067

  日期：2007.7

  Several synthetic pathways for obtaining phosphonic esters of the amino bisphosphonic acids (NBPs) pamidronate, alendronate and neridronate were investigated. The general guideline was to react N-protected amino acids activated as phthalimide esters or as acyl chlorides. Succinimide esters were found less reactive and quickly abandoned. gamma-Lactam formation arises when starting from Boc- or Cbz-protected

  研究了获得氨基双膦酸 (NBPs) pamidronate、alendronate 和 neridronate 膦酸酯的几种合成途径。一般指导原则是将 N 保护的氨基酸作为邻苯二甲酰亚胺酯或酰氯活化。发现琥珀酰亚胺酯的反应性较低并很快被废弃。当从 Boc 或 Cbz 保护的氨基酸开始时，会形成 γ-内酰胺。邻苯二甲酰亚胺 N-保护基团允许以高产率获得这三种 NBP 的烷基或芳基单酯、二酯（对称或非对称）和三酯。((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)。
• Bisphosphonate prodrugs: Synthesis and biological evaluation in HuH7 hepatocarcinoma cells
  作者：Maelle Monteil、Evelyne Migianu-Griffoni、Odile Sainte-Catherine、Mélanie Di Benedetto、Marc Lecouvey

  DOI：10.1016/j.ejmech.2014.02.054

  日期：2014.4

  We investigated the biological effects of new synthesized bisphosphonates (BPs) on HuH7 hepatocarcinoma cells. BPs containing p-bromophenyl (R-1 = p-Br, Ph, 2) in their side chain were the more potent to inhibit HuH7 cell viability. In addition, phenyl diesterified analogues (R-2 = R-3 = Ph, 2a) were more potent than methyl (R-2 = R-3 = Me, 2b) or non-esterified BPs (2) inducing more necrosis suggesting that they better entered into cells. Phosphodiesterase inhibitor (IBMX) reversed the effect of the esterified BPs and not that of non-esterified ones suggesting role of cell phosphodiesterases to release active BPs. BP analogues inhibited HuH7 cell migration but esterified ones had no effect on invasion due to the hiding of phosphonic groups. All together, these results indicated the therapeutic interest of these new BP prodrugs. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Pudovik, M. A.; Kibardina, L. K.; Pudovik, A. N., Journal of general chemistry of the USSR, 1991, vol. 61, # 5.1, p. 960 - 964
  作者：Pudovik, M. A.、Kibardina, L. K.、Pudovik, A. N.

  DOI：——

  日期：——
• Bisphosphonate prodrugs: synthesis of new aromatic and aliphatic 1-hydroxy-1,1-bisphosphonate partial esters
  作者：Maelle Monteil、Erwann Guenin、Evelyne Migianu、Didier Lutomski、Marc Lecouvey

  DOI：10.1016/j.tet.2005.05.053

  日期：2005.8

  Methods for the preparation of various 1-hydroxy-1,1-bisphosphonate partial esters were developed. They were obtained from (alkyl or phenyl) bis(trimethylsilyl) phosphite and aromatic or aliphatic acid chlorides, followed by methanolysis.

  开发了各种1-羟基-1,1-双膦酸酯偏酯的制备方法。它们是从（烷基或苯基）双（三甲基甲硅烷基）亚磷酸酯和芳族或脂族酰氯得到的，然后进行甲醇分解。
• Extremely high extraction ability of bisphosphonic acid type extraction reagent for a series of rare earth metal ions
  作者：Keisuke Ohto、Masashi Yamamoto、Shintaro Morisada、Hidetaka Kawakita

  DOI：10.1007/s10847-019-00927-5

  日期：2019.8.15

  A bisphosphonic acid type extraction reagent has been synthesised and employed to investigate the extraction behaviour towards rare-earth metals. The new reagent exhibited extremely high extraction ability for these ions. This ability was also accompanied by low leakage of extractant into the aqueous phase reflecting the reagent’s hydrophobic nature and the presence of partially undissociated phosphonic

  合成了一种双膦酸型萃取剂，并用于研究对稀土金属的萃取行为。新试剂对这些离子表现出极高的提取能力。这种能力还伴随着萃取剂进入水相的低泄漏，这反映了试剂的疏水性和部分未解离的膦酸基团的存在。