<2-(2)H,5-(2)H2>-2-Propylcyclopentanone | 168207-73-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <2-(2)H,5-(2)H2>-2-Propylcyclopentanone
• 英文别名: 2,2,5-Trideuterio-5-propylcyclopentan-1-one
• CAS: 168207-73-6
• 化学式: C₈H₁₄O
• 分子量: 129.175
• InChiKey: PFUCFFRQJFQQHE-TXXOLCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  <2-(2)H,5-(2)H2>-2-Propylcyclopentanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到(3S)-(-)-<3-(2)H,6-(2)H2>-3-Propyl-δ-valerolactone
  参考文献：
  名称：

  Biosynthesis of the Hypotensive Metabolite Oudenone by Oudemansiella radicata. 1. Intact Incorporation of a Tetraketide Chain Elongation Intermediate

  摘要：

  The biosynthesis of the fungal metabolite oudenone (1) was investigated in cultures of Oudemansiella radicata. Feeding experiments using C-13 and H-2-labeled precursors, as well as NMR analyses of the labeled metabolite, suggested a polyketide origin. The incorporation of six acetate units into the carbon skeleton of 1 was observed when cultures were fed the N-acetylcysteamine thioester derivative of C-13-labeled acetate. Labeling of oudenone (1) from [1,4-C-13(2)]succinate or L-[5-C-13]-glutamic acid was not observed, whereas the pattern of C-13 labeling from [2,3-C-13(2)]succinate was identical to that observed with [1,2-C-13(2)]acetate. The proposed advanced intermediate (5S)-5-hydroxyoctanoic acid (2) was synthesized as the deuterium labeled N-acetylcysteamine thioester derivative (S)-19 and successfully incorporated into 1. A biosynthetic scheme and cyclization mechanism, consistent with the experimental data, is proposed.

  DOI：

  10.1021/jo00126a050
• 作为产物：
  描述：

  2-氧代-1-丙基环戊烷-1-羧酸乙酯 在 diclazuril 作用下， 以 重水 为溶剂， 反应 24.0h， 生成 <2-(2)H,5-(2)H2>-2-Propylcyclopentanone
  参考文献：
  名称：

  Biosynthesis of the Hypotensive Metabolite Oudenone by Oudemansiella radicata. 1. Intact Incorporation of a Tetraketide Chain Elongation Intermediate

  摘要：

  The biosynthesis of the fungal metabolite oudenone (1) was investigated in cultures of Oudemansiella radicata. Feeding experiments using C-13 and H-2-labeled precursors, as well as NMR analyses of the labeled metabolite, suggested a polyketide origin. The incorporation of six acetate units into the carbon skeleton of 1 was observed when cultures were fed the N-acetylcysteamine thioester derivative of C-13-labeled acetate. Labeling of oudenone (1) from [1,4-C-13(2)]succinate or L-[5-C-13]-glutamic acid was not observed, whereas the pattern of C-13 labeling from [2,3-C-13(2)]succinate was identical to that observed with [1,2-C-13(2)]acetate. The proposed advanced intermediate (5S)-5-hydroxyoctanoic acid (2) was synthesized as the deuterium labeled N-acetylcysteamine thioester derivative (S)-19 and successfully incorporated into 1. A biosynthetic scheme and cyclization mechanism, consistent with the experimental data, is proposed.

  DOI：

  10.1021/jo00126a050

文献信息

• Biosynthesis of the Hypotensive Metabolite Oudenone by Oudemansiella radicata. 1. Intact Incorporation of a Tetraketide Chain Elongation Intermediate
  作者：Youla S. Tsantrizos、Fei Zhou、Parsa Famili、Xianshu Yang

  DOI：10.1021/jo00126a050

  日期：1995.10

  The biosynthesis of the fungal metabolite oudenone (1) was investigated in cultures of Oudemansiella radicata. Feeding experiments using C-13 and H-2-labeled precursors, as well as NMR analyses of the labeled metabolite, suggested a polyketide origin. The incorporation of six acetate units into the carbon skeleton of 1 was observed when cultures were fed the N-acetylcysteamine thioester derivative of C-13-labeled acetate. Labeling of oudenone (1) from [1,4-C-13(2)]succinate or L-[5-C-13]-glutamic acid was not observed, whereas the pattern of C-13 labeling from [2,3-C-13(2)]succinate was identical to that observed with [1,2-C-13(2)]acetate. The proposed advanced intermediate (5S)-5-hydroxyoctanoic acid (2) was synthesized as the deuterium labeled N-acetylcysteamine thioester derivative (S)-19 and successfully incorporated into 1. A biosynthetic scheme and cyclization mechanism, consistent with the experimental data, is proposed.