5,5-bis-(2,2,2-trifluoro-1,1-bid-trifluoromethyl-ethoxymethyl)-1,3,2-dioxathiinane 2,2-dioxide | 929552-52-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 5,5-bis-(2,2,2-trifluoro-1,1-bid-trifluoromethyl-ethoxymethyl)-1,3,2-dioxathiinane 2,2-dioxide
• 英文别名: 5,5-Bis-(2,2,2-Trifluoro-1,1-Bis-Trifluoromethyl-Ethoxymethyl)-1,3,2-Dioxathiinane 2,2-Dioxide；5,5-bis[[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]-1,3,2-dioxathiane 2,2-dioxide
• CAS: 929552-52-3
• 化学式: C₁₃H₈F₁₈O₆S
• 分子量: 634.24
• InChiKey: FXSXJKSFTBWQMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  5,5-bis-(2,2,2-trifluoro-1,1-bid-trifluoromethyl-ethoxymethyl)-1,3,2-dioxathiinane 2,2-dioxide 在 sodium azide 、 jones reagent 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 3-tert-butoxycarbonylamino-2,2-bis(2,2,2-trifluoro-1,1-bis-trifluoromethylethoxymethyl)propionic acid
  参考文献：
  名称：

  The Synthesis of a Geminally Perfluoro-tert-butylated β-Amino Acid and its Protected Forms as a Potential Pharmacokinetic Modulator and Reporter for Peptide-Based Pharmaceuticals

  摘要：

  To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (beta Fa) and its Fmoc- and Boc-protected forms were designed and synthesized. beta Fa was incorporated into a model tripeptide via standard solid-phase chemistry. Both the amino acid (free and protected) and the tripeptide show a sharp singlet F-19 NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that beta Fa is extremely hydrophobic.

  DOI：

  10.1021/jo0616308
• 作为产物：
  描述：

  2,2-bis-(2,2,2-trifluoro-1,1-bis-trifluoromethyl-ethoxymethyl)-propane-1,3-diol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.33h， 生成 5,5-bis-(2,2,2-trifluoro-1,1-bid-trifluoromethyl-ethoxymethyl)-1,3,2-dioxathiinane 2,2-dioxide
  参考文献：
  名称：

  The Synthesis of a Geminally Perfluoro-tert-butylated β-Amino Acid and its Protected Forms as a Potential Pharmacokinetic Modulator and Reporter for Peptide-Based Pharmaceuticals

  摘要：

  To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (beta Fa) and its Fmoc- and Boc-protected forms were designed and synthesized. beta Fa was incorporated into a model tripeptide via standard solid-phase chemistry. Both the amino acid (free and protected) and the tripeptide show a sharp singlet F-19 NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that beta Fa is extremely hydrophobic.

  DOI：

  10.1021/jo0616308

文献信息

• Highly fluorinated β-amino acids and methods of making and using same
  申请人：University of Utah Foundation

  公开号：US08052961B2

  公开（公告）日：2011-11-08

  Disclosed are compounds having the structure: wherein R1a and R1b are independently H, alkyl, F, or fluoroalkyl; wherein R2a, R2b, R2a′, and R2b′ are independently H, alkyl, F, fluoroalkyl, aryl, or alkenyl; wherein R3 is OH, alkoxyl, NH2, alkylamino, or dialkylamino; wherein R4a and R4b are independently H, alkyl, acyl, or alkyloxycarbonyl; wherein R11, R12, R13, R21, R22, and R23 are independently H, alkyl, F, or fluoroalkyl; and wherein C0, C1, C2 and C2′ are independently chiral or achiral. Also disclosed are processes for making a fluorinated β-amino acid comprising the steps of: providing a diol; treating the diol with a thionyl halide with oxidative workup; reacting the product with an azide salt to yield an azido group; oxidizing the product to yield a carboxyl group; and reducing the azido group to yield an amino group.

  本发明涉及具有以下结构的化合物：其中R1a和R1b独立地为H，烷基，F或氟代烷基；其中R2a，R2b，R2a'和R2b'独立地为H，烷基，F，氟代烷基，芳基或烯基；其中R3为OH，烷氧基，NH2，烷基氨基或二烷基氨基；其中R4a和R4b独立地为H，烷基，酰基或烷氧羰基；其中R11，R12，R13，R21，R22和R23独立地为H，烷基，F或氟代烷基；其中C0，C1，C2和C2'独立地手性或非手性。本发明还涉及制备氟代β-氨基酸的过程，包括以下步骤：提供二醇；用硫酰卤处理二醇并进行氧化工作；将产物与叠氮盐反应以生成叠氮基团；氧化产物以生成羧基团；还原叠氮基团以生成氨基团。
• WO2008/34093
  申请人：——

  公开号：——

  公开（公告）日：——
• The Synthesis of a Geminally Perfluoro-<i>tert</i>-butylated β-Amino Acid and its Protected Forms as a Potential Pharmacokinetic Modulator and Reporter for Peptide-Based Pharmaceuticals
  作者：Zhong-Xing Jiang、Y. Bruce Yu

  DOI：10.1021/jo0616308

  日期：2007.2.1

  To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (beta Fa) and its Fmoc- and Boc-protected forms were designed and synthesized. beta Fa was incorporated into a model tripeptide via standard solid-phase chemistry. Both the amino acid (free and protected) and the tripeptide show a sharp singlet F-19 NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that beta Fa is extremely hydrophobic.