(±)-1-oximinopyrrolizidine | 15912-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (±)-1-oximinopyrrolizidine
• 英文别名: (+/-)-1-hydroxyiminopyrrolizidine；1-oximinopyrrolizidine；1-Oximino-pyrrolizidine；N-(2,3,5,6,7,8-hexahydropyrrolizin-1-ylidene)hydroxylamine
• CAS: 15912-22-8
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: OMGXBVANAPFLSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  261.0±23.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-1-oximinopyrrolizidine 在 吡啶 、 镍 作用下， 以 异丙醇 为溶剂， 反应 11.0h， 生成 (2E)-N-[(1R,7aS)-六氢-1H-吡咯啉嗪-1-基]-3-(4-甲氧苯基)丙-2-烯酰胺
  参考文献：
  名称：

  自然合成1-酰胺基吡咯烷酮，阿布索林和拉本胺，类似物和吡咯烷并咪唑并列类似物

  摘要：

  Natural 1-amidopyrrolizidines, absouline and labumamine, were synthesized via stable pyrrolizidin-1-one hydrobromide. Amides, eater derivatives and aminopyrrolidinoimidazole analogues were also prepared and their biological activities tested. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00088-0
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 吡啶 、 盐酸羟胺 、 氢溴酸 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 7.0h， 生成 (±)-1-oximinopyrrolizidine
  参考文献：
  名称：

  自然合成1-酰胺基吡咯烷酮，阿布索林和拉本胺，类似物和吡咯烷并咪唑并列类似物

  摘要：

  Natural 1-amidopyrrolizidines, absouline and labumamine, were synthesized via stable pyrrolizidin-1-one hydrobromide. Amides, eater derivatives and aminopyrrolidinoimidazole analogues were also prepared and their biological activities tested. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00088-0

文献信息

• Suri, K. A.; Suri, O. P.; Atal, C. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. <B> 22, # 8, p. 822 - 823
  作者：Suri, K. A.、Suri, O. P.、Atal, C. K.

  DOI：——

  日期：——
• Ether bridge formation in loline alkaloid biosynthesis
  作者：Juan Pan、Minakshi Bhardwaj、Jerome R. Faulkner、Padmaja Nagabhyru、Nikki D. Charlton、Richard M. Higashi、Anne-Frances Miller、Carolyn A. Young、Robert B. Grossman、Christopher L. Schardl

  DOI：10.1016/j.phytochem.2013.11.015

  日期：2014.2

  Lolines are potent insecticidal agents produced by endophytic fungi of cool-season grasses. These alkaloids are composed of a pyrrolizidine ring system and an uncommon ether bridge linking carbons 2 and 7. Previous results indicated that 1-aminopyrrolizidine was a pathway intermediate. We used RNA interference to knock down expression of lob, resulting in the accumulation of an alkaloid identified as exo-l-acetamidopyrrolizidine based on high-resolution MS and NMR. Genomes of endophytes differing in alkaloid profiles were sequenced, revealing that those with mutated lolO accumulated exo-1-acetamidopyrrolizidine but no lolines. Heterologous expression of wild-type lolO complemented a lolO mutant, resulting in the production of N-acetylnorloline. These results indicated that the non-heme iron oxygenase, LolO, is required for ether bridge formation, probably through oxidation of exo-1-acetamidopyrrolizidine. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthèse des 1-amidopyrrolizidines naturelles, absouline et laburnamine, de dérivés et d'analogues pyrrolidinoimidazoliques
  作者：Câline Christine、Khalid Ikhiri、Alain Ahond、Ali Al Mourabit、Christiane Poupat、Pierre Potier

  DOI：10.1016/s0040-4020(00)00088-0

  日期：2000.3

  Natural 1-amidopyrrolizidines, absouline and labumamine, were synthesized via stable pyrrolizidin-1-one hydrobromide. Amides, eater derivatives and aminopyrrolidinoimidazole analogues were also prepared and their biological activities tested. (C) 2000 Elsevier Science Ltd. All rights reserved.