4-benzyloxy-3-[13C]methyl-2-methyl-4-indene | 187169-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 4-benzyloxy-3-[13C]methyl-2-methyl-4-indene
• 英文别名: 2-methyl-3-(113C)methyl-4-phenylmethoxy-1H-indene
• CAS: 187169-09-1
• 化学式: C₁₈H₁₈O
• 分子量: 251.329
• InChiKey: KHSQYLVSPWIHNK-VQEHIDDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-3-[13C]methyl-2-methyl-4-indene 在 potassium permanganate 、 sodium periodate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 84.0h， 以41%的产率得到1-[2'-(methyl-13C)acetyl-3'-benzyloxyphenyl]-2-propanone
  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：

  [13C]methylmagnesium iodide 、 7-benzyloxy-2-methyl-1-indanone 以 乙醚 为溶剂， 反应 0.67h， 以99%的产率得到4-benzyloxy-3-[13C]methyl-2-methyl-4-indene
  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

文献信息

• 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.