(4-methylbenzyl)phosphonic acid di-tert-butyl ester | 174969-89-2

• 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: (4-methylbenzyl)phosphonic acid di-tert-butyl ester
• 英文别名: 4-(di-tert-butylphosphonomethyl)toluene；Phosphonic acid, [(4-methylphenyl)methyl]-, bis(1,1-dimethylethyl) ester；1-[bis[(2-methylpropan-2-yl)oxy]phosphorylmethyl]-4-methylbenzene
• CAS: 174969-89-2
• 化学式: C₁₆H₂₇O₃P
• 分子量: 298.362
• InChiKey: KYLNDBXZFMSMIV-UHFFFAOYSA-N

物化性质

• 沸点：
  380.4±21.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-methylbenzyl)phosphonic acid di-tert-butyl ester 在 N-溴代丁二酰亚胺(NBS) 、 sodium hexamethyldisilazane 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 六甲基磷酰三胺 为溶剂， 反应 6.5h， 生成 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[4'-(di-tert-butylphosphonomethyl)benzyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
  参考文献：
  名称：

  Concise and Enantioselective Synthesis of Fmoc-Pmp(Bu^t)₂-OH and Design of Potent Pmp-Containing Grb2-SH2 Domain Antagonists

  摘要：

  L-Phosphonomethylphenylalanine (L-Pmp) is an important phosphatase-resistant pTyr analogue. A most concise and stereoselective approach to the synthesis of the suitably protected Fmoc-Pmp(Bu-t)(2)-OH was developed in order to incorporate the functionally significant L-Pmp residue into peptides and peptidomimetics efficiently using standard Fmoc protocol. With this key building block, we are able to efficiently synthesize a series of potent Pmp-containing Grb2-SH2 domain antagonists, which can be used as chemotherapeutic leads for the treatment of erbB2-overexpressed breast cancer.

  DOI：

  10.1021/ol035078+
• 作为产物：
  描述：

  二叔丁基亚磷酸盐 、 4-甲基苄溴 在 四丁基碘化铵 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以90%的产率得到(4-methylbenzyl)phosphonic acid di-tert-butyl ester
  参考文献：
  名称：

  Mild and efficient Cs2CO3-promoted synthesis of phosphonates

  摘要：

  mild and convenient synthesis for phosphonates using cesium carbonate (Cs2CO3), tetrabutylammonium iodide (TBAI) and DMF was developed at room temperature. Numerous dialkyl phosphites were screened using a diverse array of alkyl halides and these reaction conditions were found to be highly efficient producing various phosphonates exclusively in moderate to high yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.045

文献信息

• New synthesis of D,L-fmoc protected 4- phosphonomethylphenylalanine derivatives and their enzymatic resolution
  作者：Krystyna baczko、Wang-Qing Liu、Bernard P. Roques、Christlane Garbay-Jaureguiberry

  DOI：10.1016/0040-4020(95)01003-3

  日期：1996.2

  enzymatic resolution of ethyl 4-[(dimethylphosphono)methyl]-D,L-phenylalaninate succeeded. These results are discussed by comparison with the literature data. The L and D amino acids were used to prepare separately, through solid-phase peptide synthesis, followed by deprotection of dimethylphosphonate group by trimethylsilyliodide (TMSI) in acetonitrile, the L and D isomers of Glu-Asp-Val- Pmp-Glu-Asn-Leu-His-Thr

  描述了适用于固相肽合成的N - Fmoc 4-膦酰基甲基-D，L-苯丙氨酸在二叔丁基或二甲基膦酸酯形式（Fmoc-Pmp（OR）2）保护下的新合成方法。这些O的水解稳定类似物的拆分通过非对映异构体盐的部分重结晶或使用枯草杆菌蛋白酶嘉士伯酯酶尝试了β-磷酸酪氨酸。只有4-[（（二甲基膦酰基）甲基]乙基-D，L-苯丙氨酸乙酯的酶促拆分成功。通过与文献数据进行比较来讨论这些结果。氨基酸的L和d被用来分别制备，通过固相肽合成，接着在乙腈中由三甲基甲dimethylphosphonate基的脱保护（TMSI），GLU-ASP-Val-的L和d异构体PMP -Glu-ASN -Leu-His-Thr，一种肽，对应于磷酸酶PTP 1C的潜在磷酸化位点。
• Aqueous inkjet inks
  申请人：AGFA-GEVAERT NV

  公开号：US10767063B2

  公开（公告）日：2020-09-08

  An aqueous inkjet ink for forming a colour upon heat treatment includes a) an immobilized leuco dye; b) a colour developing agent or colour developing agent precursor; and c) optionally an opthothermal converting agent; wherein the leuco dye is immobilized by being covalently bonded to polymeric particles or by being included in the core of capsules composed of a polymeric shell surrounding a core.

  一种用于在热处理后形成颜色的水性喷墨墨水包括 a) 固定化的白兰地染料；b) 显色剂或显色剂前体；以及 c) 可选的光热转换剂；其中，白兰地染料通过与聚合物颗粒共价键合或包含在由围绕核心的聚合物外壳组成的胶囊核心中而被固定化。
• Mild and efficient Cs2CO3-promoted synthesis of phosphonates
  作者：Richard J Cohen、Daniel L Fox、Jarrod F Eubank、Ralph Nicholas Salvatore

  DOI：10.1016/j.tetlet.2003.09.045

  日期：2003.11

  mild and convenient synthesis for phosphonates using cesium carbonate (Cs2CO3), tetrabutylammonium iodide (TBAI) and DMF was developed at room temperature. Numerous dialkyl phosphites were screened using a diverse array of alkyl halides and these reaction conditions were found to be highly efficient producing various phosphonates exclusively in moderate to high yields. (C) 2003 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of N-fmoc protected di-tert-butyl 4-phosphonomethyl-L-phenylalanine : a hydrolytically stable analogue of O-phosphotyrosine
  作者：Wang-Qing Liu、Bernard P. Roques、Christiane Garbay-Jaureguiberry

  DOI：10.1016/0957-4166(95)00050-y

  日期：1995.3

  Fmoc-L-Pmp(tBu)(2)-OH was prepared with high enantiomeric purity by an asymmetric synthetic pathway, using a camphor sultam as chiral auxiliary.
• AQUEOUS INKJET INKS
  申请人：AGFA-GEVAERT

  公开号：US20180201798A1

  公开（公告）日：2018-07-19

  An aqueous inkjet ink for forming a colour upon heat treatment includes a) an immobilized leuco dye; b) a colour developing agent or colour developing agent precursor; and c) optionally an opthothermal converting agent; wherein the leuco dye is immobilized by being covalently bonded to polymeric particles or by being included in the core of capsules composed of a polymeric shell surrounding a core.