(8r)-Pyrrolizidin-1c-ol | 63121-29-9

• 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: (8r)-Pyrrolizidin-1c-ol
• 英文别名: (1S,8R)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-ol
• CAS: 63121-29-9
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: UCQIGQBEAGJWTF-RQJHMYQMSA-N

物化性质

• 沸点：
  206.9±23.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基丁酰氯 、 (8r)-Pyrrolizidin-1c-ol 在 吡啶 作用下， 以31%的产率得到trans (+/-)-1-(2'-methylbutyroyloxy)-pyrrolizidine
  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：

  (7S)-7-hydroxypyrrolizidin-3-one 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 (8r)-Pyrrolizidin-1c-ol
  参考文献：
  名称：

  SmI₂-Mediated Radical Cross-Couplings of α-Hydroxylated Aza-hemiacetals andN,S-Acetals with α,β-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A₂, (−)-Uniflorine A, and (+)-7-epi-Casuarine

  摘要：

  The SmI2-mediated radical coupling reactions of beta-hydroxylated pyrrolidine/piperidine aza-hemiacetals 8 and 9 and N,S-acetals 6 and 33 with alpha/beta-unsaturated compounds are described. This method allows a rapid access to beta-hydroxylated pyrrolidines, piperidines, pyrrolizidinones, and indolizidinones. Starting from N,S-acetal 33 and via a common intermediate 27, the alkaloids hyacinthacine A(2) (2), uniflorine A (3, 6-epi-casuarine), and the unnatural epimer 7-epi-casuarine (37) have been synthesized in four and five steps with overall yields of 34%, 16%, and 13%, respectively. The radical mechanism of the coupling reactions has been confirmed by controlled experiments, which also allowed deducing the anionic mechanism in the coupling between N,S-acetal 6 and carbonyl compounds. This demonstrates that the mechanisms of these SmI2-mediated reactions are switchable from Barbier-type anionic to radical by cooperative action of BF3 center dot OEt2 and t-BuOH.

  DOI：

  10.1021/jo200600n

文献信息

• SHONO, TATSUYA;KISE, NAOKI;TANABE, TAKAYOSHI, J. ORG. CHEM., 53,(1988) N 7, 1364-1367
  作者：SHONO, TATSUYA、KISE, NAOKI、TANABE, TAKAYOSHI

  DOI：——

  日期：——
• SmI₂-Mediated Radical Cross-Couplings of α-Hydroxylated Aza-hemiacetals and<i>N</i>,<i>S</i>-Acetals with α,β-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A₂, (−)-Uniflorine A, and (+)-7-<i>epi</i>-Casuarine
  作者：Xue-Kui Liu、Shi Qiu、Yong-Gang Xiang、Yuan-Ping Ruan、Xiao Zheng、Pei-Qiang Huang

  DOI：10.1021/jo200600n

  日期：2011.6.17

  The SmI2-mediated radical coupling reactions of beta-hydroxylated pyrrolidine/piperidine aza-hemiacetals 8 and 9 and N,S-acetals 6 and 33 with alpha/beta-unsaturated compounds are described. This method allows a rapid access to beta-hydroxylated pyrrolidines, piperidines, pyrrolizidinones, and indolizidinones. Starting from N,S-acetal 33 and via a common intermediate 27, the alkaloids hyacinthacine A(2) (2), uniflorine A (3, 6-epi-casuarine), and the unnatural epimer 7-epi-casuarine (37) have been synthesized in four and five steps with overall yields of 34%, 16%, and 13%, respectively. The radical mechanism of the coupling reactions has been confirmed by controlled experiments, which also allowed deducing the anionic mechanism in the coupling between N,S-acetal 6 and carbonyl compounds. This demonstrates that the mechanisms of these SmI2-mediated reactions are switchable from Barbier-type anionic to radical by cooperative action of BF3 center dot OEt2 and t-BuOH.
• 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.