4-hydroxydec-2-ynoic acid | 804474-92-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 4-hydroxydec-2-ynoic acid
• CAS: 804474-92-8
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: MSBRBLRVGRWQPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxydec-2-ynoic acid 在 咪唑 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.08h， 生成 4-tert-butyldimethylsiloxydec-2-ynoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Deuterated γ-Lactones for Use in Stable Isotope Dilution Assays

  摘要：

  Two syntheses of deuterated gamma-lactones for use as internal standards in stable isotope dilution assays (SIDA) were developed. [2,2,3,3-H-2(4)]-gamma-Octa-, -gamma-deca-, and -gamma-dodecalactones with > 89% deuterium incorporation were prepared in 27, 17, and 19% overall yields, respectively, by the reduction of a doubly protected hydroxypropiolic acid with deuterium gas. [3,3,4-H-2(3)]-gamma-Octa- and -gamma-dodecalactones were prepared in 6 and 23% yields with > 92% deuterium incorporation by the free radical addition of 2-iodoacetamide to [1,1,2-H-2(3)]-1-hexene and [1,1,2-H-2(3)]-1-decene, respectively. Reaction yields were highly dependent upon the purity of the 1-alkene starting material. The deuterated gamma-lactones were evaluated as internal standards for SIDA.

  DOI：

  10.1021/jf048885b
• 作为产物：
  描述：

  庚醛 、 丙炔酸 在 四甲基乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以44%的产率得到4-hydroxydec-2-ynoic acid
  参考文献：
  名称：

  Synthesis of Deuterated γ-Lactones for Use in Stable Isotope Dilution Assays

  摘要：

  Two syntheses of deuterated gamma-lactones for use as internal standards in stable isotope dilution assays (SIDA) were developed. [2,2,3,3-H-2(4)]-gamma-Octa-, -gamma-deca-, and -gamma-dodecalactones with > 89% deuterium incorporation were prepared in 27, 17, and 19% overall yields, respectively, by the reduction of a doubly protected hydroxypropiolic acid with deuterium gas. [3,3,4-H-2(3)]-gamma-Octa- and -gamma-dodecalactones were prepared in 6 and 23% yields with > 92% deuterium incorporation by the free radical addition of 2-iodoacetamide to [1,1,2-H-2(3)]-1-hexene and [1,1,2-H-2(3)]-1-decene, respectively. Reaction yields were highly dependent upon the purity of the 1-alkene starting material. The deuterated gamma-lactones were evaluated as internal standards for SIDA.

  DOI：

  10.1021/jf048885b