2,2-bis(trifluoromethyl)-1,3-dioxolan-5-(4-nitropnenyl)-4-one

• 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: 2,2-bis(trifluoromethyl)-1,3-dioxolan-5-(4-nitropnenyl)-4-one
• 英文别名: 5-(4-Nitrophenyl)-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one
• 化学式: C₁₁H₅F₆NO₅
• 分子量: 345.155
• InChiKey: DQZKHJBPFJZTCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-羟基-2-(4-硝基苯基)乙酸甲酯 、 六氟丙酮 在 盐酸 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 以0.54 g的产率得到2,2-bis(trifluoromethyl)-1,3-dioxolan-5-(4-nitropnenyl)-4-one
  参考文献：
  名称：

  p-Nitromandelic Acid as a Highly Acid-Stable Safety-Catch Linker for Solid-Phase Synthesis of Peptide and Depsipeptide Acids

  摘要：

  p-Nitromandelic acid as a safety-catch linker for Boc/Bzl-SPPS of base-labile compounds like peptides and depsipeptides is described. This linker permits acidic removal of side-chain protection groups from the resin. For cleavage from the solid support, the p-nitro group was reduced with tin(II) chloride. After washing off the reducing agents, the (depsi)peptide acids with or without the side-chain protection schemes were obtained by microwave irradiation at 50 degrees C with 5% TFA in dioxane.

  DOI：

  10.1021/ol063148h

文献信息

• <i>p</i>-Nitromandelic Acid as a Highly Acid-Stable Safety-Catch Linker for Solid-Phase Synthesis of Peptide and Depsipeptide Acids
  作者：Albert Isidro-Llobet、Mercedes Alvarez、Klaus Burger、Jan Spengler、Fernando Albericio

  DOI：10.1021/ol063148h

  日期：2007.4.1

  p-Nitromandelic acid as a safety-catch linker for Boc/Bzl-SPPS of base-labile compounds like peptides and depsipeptides is described. This linker permits acidic removal of side-chain protection groups from the resin. For cleavage from the solid support, the p-nitro group was reduced with tin(II) chloride. After washing off the reducing agents, the (depsi)peptide acids with or without the side-chain protection schemes were obtained by microwave irradiation at 50 degrees C with 5% TFA in dioxane.