(E)-2-(5-heptenyl)-6,7,8,8a-tetrahydro-8-hydroxy-3-methyl-4H-pyrrolo[2,1-b][1,3]oxazin-4-one | 255869-45-5

• 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: (E)-2-(5-heptenyl)-6,7,8,8a-tetrahydro-8-hydroxy-3-methyl-4H-pyrrolo[2,1-b][1,3]oxazin-4-one
• 英文别名: 2-hept-5-enyl-6,7-dihydro-8(8aH)-hydroxy-3-methyl-4H-pyrrole[2,1-b][1,3]oxazine-4-one；2-[(E)-hept-5-enyl]-8-hydroxy-3-methyl-6,7,8,8a-tetrahydropyrrolo[2,1-b][1,3]oxazin-4-one
• CAS: 255869-45-5
• 化学式: C₁₅H₂₃NO₃
• 分子量: 265.353
• InChiKey: WRQPHAWWEMJGCD-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(5-heptenyl)-6,7,8,8a-tetrahydro-8-hydroxy-3-methyl-4H-pyrrolo[2,1-b][1,3]oxazin-4-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到(E)-2-(5-heptenyl)-6,7-dihydro-8-hydroxy-3-methyl-4H-pyrrolo[2,1-b][1,3]oxazine-4,8(8aH)-dione
  参考文献：
  名称：

  Synthesis of racemic brevioxime

  摘要：

  盐酸胺12和β-酮硫酯16经偶联并经TFA处理后，得到醇18，随后进行氧化反应，转化为肟20的混合物。肟混合物中的主要产物，外消旋短肟1，得以分离。

  DOI：

  10.1039/a906579b
• 作为产物：
  描述：

  (E)-2-辛烯醇 在 咪唑 、 lithium hydroxide 、 草酰氯 、 四丁基氟化铵 、 对甲苯磺酸 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 (E)-2-(5-heptenyl)-6,7,8,8a-tetrahydro-8-hydroxy-3-methyl-4H-pyrrolo[2,1-b][1,3]oxazin-4-one
  参考文献：
  名称：

  Nishimura, Yutaka; Kitahara, Takeshi, Heterocycles, 2000, vol. 52, # 2, p. 553 - 556

  摘要：

  DOI：

文献信息

• Synthesis of Racemic Brevioxime and Related Model Compounds
  作者：Derrick L. J. Clive、Soleiman Hisaindee

  DOI：10.1021/jo0003551

  日期：2000.8.1

  The synthesis, in racemic form, of the insect juvenile hormone inhibitor brevioxime (1) is described, as well as exploratory studies that led to the related model compounds 14 and 15a. The route to 1 involves Ag(+)-mediated coupling of the amine derived from 20 with the beta-keto thioester 32. Acid treatment of the coupled product 33 led by acetal hydrolysis, cyclization, and desilylation to 34a,b

  描述了昆虫幼体激素抑制剂brevioxime（1）的外消旋形式合成，以及探索性研究导致了相关模型化合物14和15a的合成。通往1的途径涉及Ag（+）介导的20衍生的胺与β-酮硫酯32的偶联。偶联产物33的酸处理由乙缩醛水解，环化和去甲硅烷基化作用生成34a，b，从中得到1通过氧化并转化为肟达到目的。在氨基组分20的合成中，已知但不寻常的还原用于将腈转化为胺盐酸盐。
• Synthesis of racemic brevioxime
  作者：Derrick L. J. Clive、Soleiman Hisaindee

  DOI：10.1039/a906579b

  日期：——

  Amine hydrochloride 12 and β-keto thioester 16 were coupled and treated with TFA; the resulting alcohols 18 were oxidized and converted into a mixture of oximes 20, from which the major product, racemic brevioxime 1, was isolated.

  盐酸胺12和β-酮硫酯16经偶联并经TFA处理后，得到醇18，随后进行氧化反应，转化为肟20的混合物。肟混合物中的主要产物，外消旋短肟1，得以分离。
• 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.
• Nishimura, Yutaka; Kitahara, Takeshi, Heterocycles, 2000, vol. 52, # 2, p. 553 - 556
  作者：Nishimura, Yutaka、Kitahara, Takeshi

  DOI：——

  日期：——
• 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.