(8E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec-8-ene-1,3-dione | 302555-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec-8-ene-1,3-dione
• 英文别名: (E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec-8-ene-1,3-dione；N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline；(E)-1-(2,3-dihydropyrrol-1-yl)-2-methyldec-8-ene-1,3-dione
• CAS: 302555-38-0
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: JGNMZTXDOHXIJQ-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (8E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec-8-ene-1,3-dione 在 nitrosonium tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到(E)-2-(hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazine
  参考文献：
  名称：

  A Rapid Synthesis of Racemic Brevioxime

  摘要：

  由N-丙酰基-2-吡咯啉出发，通过使用亚硝酰氯的β-酮酰胺分子内环化反应，已合成了外消旋的短环昔脒。

  DOI：

  10.1055/s-2001-10769
• 作为产物：
  描述：

  (E)-1-(3-Hydroxy-pyrrolidin-1-yl)-2-methyl-dec-8-ene-1,3-dione 在 potassium tert-butylate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 (8E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec-8-ene-1,3-dione
  参考文献：
  名称：

  Synthesis of (−)-Brevioxime

  摘要：

  The synthesis of(-)-Brevioxime and related JH biosynthesis inhibitor 1 was accomplished in nine steps from 3-hydroxypyrrolidine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00586-x

文献信息

• Isolation and Synthesis ofN-(2-Methyl-3-oxodec-8-enoyl)-2-pyrroline and 2-(Hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]1,3-oxazine – Two New Fungal Metabolites with in vivo Anti-Juvenile-Hormone and Insecticidal Activity
  作者：Ángel Cantín、Pilar Moya、Maria-Angeles Castillo、Jaime Primo、Miguel A. Miranda、Eduardo Primo-Yúfera

  DOI：10.1002/(sici)1099-0690(199901)1999:1<221::aid-ejoc221>3.0.co;2-y

  日期：1999.1

  have been isolated from Penicillium brevicompactum Dierckx. Compound 2 has shown an important in vivo anti-juvenile-hormone (anti-JH) activity while compound 3 has exhibited insecticidal activity against Oncopeltus fasciatus Dallas. Both products have been synthesized starting from 1,4-hexadiene, by means of a sequence of reactions which includes the preparation of 6-octenoic acid and its transformation

  两种新的天然产物，N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (2) 和 2-(hept-5-enyl)-3-methyl-4-oxo-6,7， 8,8a-四氢-4H-吡咯并[2,1-b]-1,3-恶嗪(3)，已从Penicillium brevicompactum Dierckx 中分离出来。化合物 2 显示出重要的体内抗保幼激素 (anti-JH) 活性，而化合物 3 显示出对 Oncopeltus fasciatus Dallas 的杀虫活性。两种产品均由 1,4-己二烯通过一系列反应合成，包括制备 6-辛烯酸并将其转化为相应的酰氯，以酰化 Meldrum 酸。随后用吡咯烷氨解，然后用碘甲烷在 β-氧代酰胺的活化位置甲基化，通过阳极氧化在吡咯烷环上引入甲氧基并最终在 SiO2 上消除甲醇导致 2 和 3。两种代谢物可以通过相同序列制备的事实表明
• 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.
• 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.
• A Rapid Synthesis of Racemic Brevioxime
  作者：Philip J. Parsons、Burhan Karadogan、Jacqueline A. Macritchie

  DOI：10.1055/s-2001-10769

  日期：——

  Racemic brevioxime has been synthesised starting from N-propionyl-2-pyrroline by intramolecular cyclisation of a β-ketoamide using nitrosyl chloride.

  由N-丙酰基-2-吡咯啉出发，通过使用亚硝酰氯的β-酮酰胺分子内环化反应，已合成了外消旋的短环昔脒。
• Synthesis of (−)-Brevioxime
  作者：D Clark

  DOI：10.1016/s0040-4020(00)00586-x

  日期：2000.8.18

  The synthesis of(-)-Brevioxime and related JH biosynthesis inhibitor 1 was accomplished in nine steps from 3-hydroxypyrrolidine. (C) 2000 Elsevier Science Ltd. All rights reserved.