[1,2-13C2]-3-hexyn-2,5-diyl bis(tert-butyl carbonate) | 191528-22-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: [1,2-13C2]-3-hexyn-2,5-diyl bis(tert-butyl carbonate)
• 英文别名: tert-butyl 5-[(2-methylpropan-2-yl)oxycarbonyloxy](1,2-13C2)hex-3-yn-2-yl carbonate
• CAS: 191528-22-0
• 化学式: C₁₆H₂₆O₆
• 分子量: 316.357
• InChiKey: BRKODJVQHOFETM-HAZFEAMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1,2-13C2]-3-hexyn-2,5-diyl bis(tert-butyl carbonate) 在 potassium permanganate 、 草酸 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 10.5h， 生成 4-hydroxy-5-[13C]methyl-2-methyl-3(2H)-[5-13C]furanone
  参考文献：
  名称：

  Determination of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-Ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in Pentose Sugar-Based Maillard Model Systems by Isotope Dilution Assays

  摘要：

  The formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone (EHMF) from pentose sugars was studied in Maillard model systems. The amounts generated at 90 degrees C for 1 h were determined by isotope dilution assay (IDA). The internal standards used for IDA, i.e., [C-13(2)]HDMF and [H-2(3)]EHMF, were prepared in good overall yields in three steps: addition of labeled acetaldehyde or propionaldehyde to tert-butyloxycarbonyl (Boc)-protected and lithiated 3-butyn-2-ol; oxidation of the Boc-protected diol with permanganate to 1,2-dione; and finally cyclization to the target molecules after removal of the protective groups under acidic conditions. Quantitative data confirmed previous findings that HDMF and EHMF are preferentially formed in the presence of glycine and L-alanine, respectively. The yields obtained were 2.6-5.1 mu g of HDMF and 6.8- 10 mu g of EHMF per mmol pentose. Formation of both furanones was favored in phosphate-buffered solutions at pH 7 compared to pH 5, particularly in the presence of an excess of amino acid. These data are well in agreement with the previously proposed formation mechanism of HDMF and EHMF via Strecker-assisted chain elongation of the pentose moiety. However, both furanones were also produced to a lesser extent by sugar fragmentation-condensation reactions.

  DOI：

  10.1021/jf960997i
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 lithium diisopropyl amide 作用下， 生成 [1,2-13C2]-3-hexyn-2,5-diyl bis(tert-butyl carbonate)
  参考文献：
  名称：

  Determination of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-Ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in Pentose Sugar-Based Maillard Model Systems by Isotope Dilution Assays

  摘要：

  The formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone (EHMF) from pentose sugars was studied in Maillard model systems. The amounts generated at 90 degrees C for 1 h were determined by isotope dilution assay (IDA). The internal standards used for IDA, i.e., [C-13(2)]HDMF and [H-2(3)]EHMF, were prepared in good overall yields in three steps: addition of labeled acetaldehyde or propionaldehyde to tert-butyloxycarbonyl (Boc)-protected and lithiated 3-butyn-2-ol; oxidation of the Boc-protected diol with permanganate to 1,2-dione; and finally cyclization to the target molecules after removal of the protective groups under acidic conditions. Quantitative data confirmed previous findings that HDMF and EHMF are preferentially formed in the presence of glycine and L-alanine, respectively. The yields obtained were 2.6-5.1 mu g of HDMF and 6.8- 10 mu g of EHMF per mmol pentose. Formation of both furanones was favored in phosphate-buffered solutions at pH 7 compared to pH 5, particularly in the presence of an excess of amino acid. These data are well in agreement with the previously proposed formation mechanism of HDMF and EHMF via Strecker-assisted chain elongation of the pentose moiety. However, both furanones were also produced to a lesser extent by sugar fragmentation-condensation reactions.

  DOI：

  10.1021/jf960997i

文献信息

• Determination of 4-Hydroxy-2,5-dimethyl-3(2<i>H</i>)-furanone and 2(or 5)-Ethyl-4-hydroxy-5(or 2)-methyl-3(2<i>H</i>)-furanone in Pentose Sugar-Based Maillard Model Systems by Isotope Dilution Assays
  作者：Imre Blank、Laurent B. Fay、Frederick J. Lakner、Manfred Schlosser

  DOI：10.1021/jf960997i

  日期：1997.7.1

  The formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone (EHMF) from pentose sugars was studied in Maillard model systems. The amounts generated at 90 degrees C for 1 h were determined by isotope dilution assay (IDA). The internal standards used for IDA, i.e., [C-13(2)]HDMF and [H-2(3)]EHMF, were prepared in good overall yields in three steps: addition of labeled acetaldehyde or propionaldehyde to tert-butyloxycarbonyl (Boc)-protected and lithiated 3-butyn-2-ol; oxidation of the Boc-protected diol with permanganate to 1,2-dione; and finally cyclization to the target molecules after removal of the protective groups under acidic conditions. Quantitative data confirmed previous findings that HDMF and EHMF are preferentially formed in the presence of glycine and L-alanine, respectively. The yields obtained were 2.6-5.1 mu g of HDMF and 6.8- 10 mu g of EHMF per mmol pentose. Formation of both furanones was favored in phosphate-buffered solutions at pH 7 compared to pH 5, particularly in the presence of an excess of amino acid. These data are well in agreement with the previously proposed formation mechanism of HDMF and EHMF via Strecker-assisted chain elongation of the pentose moiety. However, both furanones were also produced to a lesser extent by sugar fragmentation-condensation reactions.