1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione | 236121-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione
• 英文别名: N-(2-methyl-3-oxo-decanoyl)-2-pyrroline；N-(2-methyl-3-oxodecanoyl)-2-pyrroline；N-(2-methyl-3-oxodecanoyl)pyrroline；1-(2,3-dihydropyrrol-1-yl)-2-methyldecane-1,3-dione
• CAS: 236121-02-1；217813-11-1
• 化学式: C₁₅H₂₅NO₂
• 分子量: 251.369
• InChiKey: HMWIYUSLKIYYER-UHFFFAOYSA-N

物化性质

• 沸点：
  390.8±31.0 °C(predicted)
• 密度：
  1.003±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione 在 Oxone 、 盐酸羟胺 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 2-heptyl-6,7-dihydro-3-methyl-4H-pyrrole[2,1-b][1,3]oxazine-4,8(8aH)-dione 8-oxime
  参考文献：
  名称：

  Novel Inhibitors of the Mitochondrial Respiratory Chain:  Oximes and Pyrrolines Isolated from Penicillium brevicompactum and Synthetic Analogues

  摘要：

  The capacity of inhibition of the mammalian mitochondrial respiratory chain of brevioxime 5a, a natural insecticide compound isolated from Penicillium brevicompactum culture broth, and another 15 analogue compounds, other oximes 5b and 5c; two diastereomeric pyrrolidines 1c' and 1c"; five pyrrolines 3c', 3c" (diastereomers between them), 3a, 3b, and 6; two oxazines 4c' and 4c" (also diastereomers between them); and four pyrrol derivatives 7-10, are analyzed in this paper. Compounds 3b, 3c', 3c", 4c', 4c", 5b, 5c, 6, and 10 were found to be inhibitors of the integrated electron transfer chain (NADH oxidase activity) in beef heart submitochondrial particles (SMP), establishing that all of them except compound 3b and 6 only affected to complex I of the mitochondrial respiratory chain. The most potent product was 5b, with an IC50 of 0.27 mu M, similar to the IC50 values of other known complex I inhibitors. The diastereomeric pairs 1 c'/1c", 3c'/3c", 4c'/4c", and 5c have not been previously described. Chemical characterization, on the basis of spectral data, is also shown.

  DOI：

  10.1021/jf058075f
• 作为产物：
  描述：

  N-(2-methyl-3-oxodecanoyl)pyrrolidine 在 四丁基对甲苯磺酸铵 、 silica gel 作用下， 反应 2.75h， 生成 1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione
  参考文献：
  名称：

  Isolation, Structural Assignment, and Synthesis of N-(2-Methyl-3-oxodecanoyl)-2-pyrroline, a New Natural Product from Penicillium brevicompactum with in Vivo Anti-Juvenile Hormone Activity

  摘要：

  A new natural product with in vivo anti-juvenile hormone (JK) activity, N-(2-methyl-3-oxodecanoyl)-2-pyrroline (2), has been isolated from Penicillium brevicompactum Dierckx. Its structure has been tentatively assigned based on spectral data and unambiguously confirmed by alternative syntheses. Compound 2 has been prepared by means of a sequence of reactions beginning with acylation of Meldrum's acid by octanoyl chloride. The subsequent steps have been aminolysis of the resultant intermediate with pyrrolidine,;alkylation of the active position with iodomethane, introduction of a methoxy group in the pyrrolidine ring by anodic oxidation, and final elimination of methanol through adsorption on SiO2 and heating. The natural product 2 and its bicyclic isomer 2-heptyl-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo [2,1-b]-1,3-oxazine (3) are also obtained. This reveals that 2 can be biogenetically related to the recently discovered brevioxime (1). Compound 2 and the synthetic precursors of 2 have shown important biological activities as insecticides (against Oncopeltus fasciatus Dallas) and fungicides. The natural product induces precocious metamorphosis in the target insect (70% precocious adults at 10 mu g/nymph). In view of the above results, these products could be useful as lead molecules for the synthesis of analogues with enhanced biological activities.

  DOI：

  10.1021/jo972267v

文献信息

• Synthesis of racemic brevioxime and related analogues
  作者：Burhan Karadogan、Philip J Parsons

  DOI：10.1016/s0040-4020(01)00835-3

  日期：2001.10

  Racemic brevioxime and the related model compounds have been synthesised starting from N-propionyl-2-pyrroline by intramolecular cyclisation of a beta -ketoamide using nitrosyl chloride. (C) 2001 Published by Elsevier Science Ltd.
• Isolation, Structural Assignment, and Synthesis of <i>N</i>-(2-Methyl-3-oxodecanoyl)-2-pyrroline, a New Natural Product from <i>Penicillium </i><i>b</i><i>revicompactum</i> with in Vivo Anti-Juvenile Hormone Activity
  作者：Pilar Moya、Ángel Cantín、Maria-Angeles Castillo、Jaime Primo、Miguel A. Miranda、Eduardo Primo-Yúfera

  DOI：10.1021/jo972267v

  日期：1998.11.1

  A new natural product with in vivo anti-juvenile hormone (JK) activity, N-(2-methyl-3-oxodecanoyl)-2-pyrroline (2), has been isolated from Penicillium brevicompactum Dierckx. Its structure has been tentatively assigned based on spectral data and unambiguously confirmed by alternative syntheses. Compound 2 has been prepared by means of a sequence of reactions beginning with acylation of Meldrum's acid by octanoyl chloride. The subsequent steps have been aminolysis of the resultant intermediate with pyrrolidine,;alkylation of the active position with iodomethane, introduction of a methoxy group in the pyrrolidine ring by anodic oxidation, and final elimination of methanol through adsorption on SiO2 and heating. The natural product 2 and its bicyclic isomer 2-heptyl-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo [2,1-b]-1,3-oxazine (3) are also obtained. This reveals that 2 can be biogenetically related to the recently discovered brevioxime (1). Compound 2 and the synthetic precursors of 2 have shown important biological activities as insecticides (against Oncopeltus fasciatus Dallas) and fungicides. The natural product induces precocious metamorphosis in the target insect (70% precocious adults at 10 mu g/nymph). In view of the above results, these products could be useful as lead molecules for the synthesis of analogues with enhanced biological activities.
• Novel Inhibitors of the Mitochondrial Respiratory Chain:  Oximes and Pyrrolines Isolated from <i>Penicillium brevicompactum</i> and Synthetic Analogues
  作者：Ángel Cantín、M. Pilar López-Gresa、M. Carmen González、Pilar Moya、Miguel Ángel Miranda、Jaime Primo、Vanessa Romero、Eva Peris、Ernesto Estornell

  DOI：10.1021/jf058075f

  日期：2005.10.1

  The capacity of inhibition of the mammalian mitochondrial respiratory chain of brevioxime 5a, a natural insecticide compound isolated from Penicillium brevicompactum culture broth, and another 15 analogue compounds, other oximes 5b and 5c; two diastereomeric pyrrolidines 1c' and 1c"; five pyrrolines 3c', 3c" (diastereomers between them), 3a, 3b, and 6; two oxazines 4c' and 4c" (also diastereomers between them); and four pyrrol derivatives 7-10, are analyzed in this paper. Compounds 3b, 3c', 3c", 4c', 4c", 5b, 5c, 6, and 10 were found to be inhibitors of the integrated electron transfer chain (NADH oxidase activity) in beef heart submitochondrial particles (SMP), establishing that all of them except compound 3b and 6 only affected to complex I of the mitochondrial respiratory chain. The most potent product was 5b, with an IC50 of 0.27 mu M, similar to the IC50 values of other known complex I inhibitors. The diastereomeric pairs 1 c'/1c", 3c'/3c", 4c'/4c", and 5c have not been previously described. Chemical characterization, on the basis of spectral data, is also shown.