pivalic [1,2-13C2]acetic anhydride | 187168-93-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: pivalic [1,2-13C2]acetic anhydride
• 英文别名: Acetyl 2,2-dimethylpropanoate
• CAS: 187168-93-0
• 化学式: C₇H₁₂O₃
• 分子量: 146.148
• InChiKey: XRZGYORMSVQTJF-AEGZSVGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[3,5-Bis(benzyloxy)phenyl]acetone 、 pivalic [1,2-13C2]acetic anhydride 在 tetrafluoroboric acid 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以80%的产率得到6,8-dibenzyloxy-1,3-[1,1'-13C2]dimethyl-2-benzopyrylium tetrafluoroborate
  参考文献：
  名称：

  Labelled precursors for biosynthetic studies on naphthylisoquinoline alkaloids

  摘要：

  The isotope labelled monocyclic ketones 5 and 8, postulated precursors to the presumably acetogenic naphthylisoquinoline alkaloids, have been synthesized for biogenetic experiments to Ancistrocladaceae and Dioncophyllacene plants. Key step of the preparation of 1-(2'-[carbonyl-C-14]acetyl-3',5'-dibenzyloxyphenyl)-2-propanone ([C-14]-13) is the C-acetylation of the arylpropanone 10 with the mixed pivalic acetic anhydride ([C-14]-11). The resulting pyrylium salt [C-14]-13, which is stable and can be stored, is cleaved directly before the feeding experiment to give the diketone [C-14]-13 and deprotected to give the free phenolic target molecule [C-14]-5. This synthetic route is applicable also to the prepation of 1-(2'-[C-13(2)]acetyl-3'-hydroxyphenyl)-2-propanone ([C-13(2)]-5) for biosynthetic experiments with NMR analysis. For the preparation of the oxygen-poorer C-13-labelled diketone I-(2'-[methyl-C-13]acetyl-3'-hydroxyphenyl)-2-propanone ([C-13]-8), an 'indanone-route' has been elaborated.

  DOI：

  10.1002/(sici)1099-1344(199701)39:1<29::aid-jlcr936>3.0.co;2-y
• 作为产物：
  描述：

  三甲基乙酰氯 、 乙酸钠-13C2 以 四氢呋喃 为溶剂， 生成 pivalic [1,2-13C2]acetic anhydride
  参考文献：
  名称：

  同位素标记的C-3中心不对称的L-α-氨基酸的合成

  摘要：

  描述了合成一系列同位素标记的L -α-氨基酸的方法，每个氨基酸在C-3处具有不对称中心，包括异亮氨酸， 同种异亮氨酸， 苏氨酸 和 异基因-苏氨酸。所述方法可以简单地适于将同位素标记物选择性地掺入到所述细胞的每个位点。大号缬氨酸 包括对非对映异构体的选择性标记 甲基 碳13和/或氘和 贴标 的 胺 和 氮15。

  DOI：

  10.1039/b005172l

文献信息

• Syntheses of isotopically labelled L-α-amino acids with an asymmetric centre at C-3
  作者：John R. Harding、Rachael A. Hughes、Nicholas M. Kelly、Andrew Sutherland、Christine L. Wilis

  DOI：10.1039/b005172l

  日期：——

  Approaches are described to the synthesis of a series of isotopically labelled L-α-amino acids each with an asymmetric centre at C-3, including isoleucine, allo-isoleucine, threonine and allo-threonine. The methods may be simply adapted for the selective incorporation of an isotopic label at each site of L-valine including the selective labelling of either diastereotopic methyl group with carbon-13

  描述了合成一系列同位素标记的L -α-氨基酸的方法，每个氨基酸在C-3处具有不对称中心，包括异亮氨酸， 同种异亮氨酸， 苏氨酸 和 异基因-苏氨酸。所述方法可以简单地适于将同位素标记物选择性地掺入到所述细胞的每个位点。大号缬氨酸 包括对非对映异构体的选择性标记 甲基 碳13和/或氘和 贴标 的 胺 和 氮15。
• Labelled precursors for biosynthetic studies on naphthylisoquinoline alkaloids
  作者：Gerhard Bringmann、Frank Pokorny、Matthias Wenzel、Kathi Wurm、Christoph Schneider

  DOI：10.1002/(sici)1099-1344(199701)39:1<29::aid-jlcr936>3.0.co;2-y

  日期：1997.1

  The isotope labelled monocyclic ketones 5 and 8, postulated precursors to the presumably acetogenic naphthylisoquinoline alkaloids, have been synthesized for biogenetic experiments to Ancistrocladaceae and Dioncophyllacene plants. Key step of the preparation of 1-(2'-[carbonyl-C-14]acetyl-3',5'-dibenzyloxyphenyl)-2-propanone ([C-14]-13) is the C-acetylation of the arylpropanone 10 with the mixed pivalic acetic anhydride ([C-14]-11). The resulting pyrylium salt [C-14]-13, which is stable and can be stored, is cleaved directly before the feeding experiment to give the diketone [C-14]-13 and deprotected to give the free phenolic target molecule [C-14]-5. This synthetic route is applicable also to the prepation of 1-(2'-[C-13(2)]acetyl-3'-hydroxyphenyl)-2-propanone ([C-13(2)]-5) for biosynthetic experiments with NMR analysis. For the preparation of the oxygen-poorer C-13-labelled diketone I-(2'-[methyl-C-13]acetyl-3'-hydroxyphenyl)-2-propanone ([C-13]-8), an 'indanone-route' has been elaborated.
• Synthesis and Incorporation of the First Polyketide Synthase Free Intermediate in Monocerin Biosynthesis
  作者：Lorraine C. Axford、Thomas J. Simpson、Christine L. Willis

  DOI：10.1002/anie.200352652

  日期：2004.1.30