3-triethylsilyloxy-N-propionylpyrrolidine | 302555-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-triethylsilyloxy-N-propionylpyrrolidine
• 英文别名: 1-(3-Triethylsilyloxypyrrolidin-1-yl)propan-1-one
• CAS: 302555-42-6
• 化学式: C₁₃H₂₇NO₂Si
• 分子量: 257.448
• InChiKey: NEQBIZDEVUNRHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-triethylsilyloxy-N-propionylpyrrolidine 在 potassium tert-butylate 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 23.0h， 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
• 作为产物：
  描述：

  三乙基氯硅烷 以 吡啶 为溶剂， 反应 32.0h， 生成 3-triethylsilyloxy-N-propionylpyrrolidine
  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

• 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.
• 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.