1H-吡咯-1-羧酸,5-溴-2,5-二氢-3-甲基-2-羰基-,1,1-二甲基乙基酯 | 181635-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 1H-吡咯-1-羧酸,5-溴-2,5-二氢-3-甲基-2-羰基-,1,1-二甲基乙基酯
• 英文名称: 5-bromo-1-tert-butoxycarbonyl-3-methyl-3-pyrrolin-2-one
• 英文别名: tert-butyl 5-bromo-3-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate；tert-butyl 2-bromo-4-methyl-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 181635-59-6
• 化学式: C₁₀H₁₄BrNO₃
• 分子量: 276.13
• InChiKey: FJIVVUCTFVMRAC-UHFFFAOYSA-N

物化性质

• 沸点：
  292.1±50.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-吡咯-1-羧酸,5-溴-2,5-二氢-3-甲基-2-羰基-,1,1-二甲基乙基酯 在 sodium hydride 、 二甲基亚砜 作用下， 以 苯 为溶剂， 反应 19.0h， 生成 3-Methyl-2-oxo-5-(triphenyl-λ⁵-phosphanylidene)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  （5E）-和（5Z）-5-亚苄基-3-甲基-3-吡咯啉-2-酮的立体选择性制备。在合成氨苄青霉素和异氨苄青霉素中的应用

  摘要：

  N-Boc-5-膦基亚烷基-和N-Boc-5-二乙基膦酸酯-3-甲基-3-吡咯啉-2-酮在（5E）-和（5Z）-3-甲基-5的立体选择性合成中的应用检查了-亚苄基-3-吡咯啉-2-酮。还已经通过使用两种Wittig中间体实现了生长调节剂Ampullicin和Isoampullicin的立体选择性合成。

  DOI：

  10.1016/0040-4039(96)01232-4
• 作为产物：
  描述：

  3-甲基-2-吡咯烷酮 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 为溶剂， 反应 9.5h， 生成 1H-吡咯-1-羧酸,5-溴-2,5-二氢-3-甲基-2-羰基-,1,1-二甲基乙基酯
  参考文献：
  名称：

  Total Synthesis of (+)-Ampullicin and (+)-Isoampullicin:  Two Fungal Metabolites with Growth Regulatory Activity Isolated from Ampulliferina Sp. 27

  摘要：

  The total synthesis of the growth regulators (+)-ampullicin 1 and (+)-isoampullicin 2 from (R)(-)-carvone 5 was accomplished by application of an 18-step sequence with 4.5% overall yield. The crucial step of the synthetic strategy lies on the internal displacement of tosylate 13 by means of the lactone enolate. In this way, access was opened to the tricyclic core present in these biologically active sesquiterpenic amides. A Horner-Emmons reaction between the carbaldehyde 16 and the phosphonate 22 led us to the stereoselective preparation of (+)-ampullicin 1. Standard transformation of I into the thermodynamically more stable geometric isomer (+)-isoampullicin 2 was trivial. The absolute configuration of both amides was established by X-ray analysis of a sample of synthetic (+)-isoampullicin 2.

  DOI：

  10.1021/jo010527+

文献信息

• Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step
  作者：Chiara Lombardi、Emma Artuso、Eleonora Grandi、Marco Lolli、Francesca Spirakys、Emanuele Priola、Cristina Prandi

  DOI：10.1039/c7ob01917c

  日期：——

  Structural analogues of natural strigolactones in which the butenolide D-ring has been replaced with γ-lactam. The key step was an RCM on suitably substituted amides.

  将天然分枝酮的结构类似物中的丁烯内酯D环替换为γ-内酰胺。关键步骤是在适当取代的酰胺上进行环状烯烃交叉二聚反应。
• Stereoselective preparation of (5E)- and (5Z)-5-benzylidene-3-methyl-3-pyrrolin-2-ones. Application to the synthesis of ampullicine and isoampullicine
  作者：Rosario Rico、Francisco Bermejo

  DOI：10.1016/0040-4039(96)01232-4

  日期：1996.8

  The application of N-Boc-5-phosphoranylidene- and N-Boc-5-diethylphosphonate-3-methyl-3-pyrrolin-2-ones to the stereoselective synthesis of (5E)- and (5Z)-3-methyl-5-benzylidene-3-pyrrolin-2-ones is examined. The stereoselective synthesis of the growth regulators Ampullicin and Isoampullicin by using both Wittig intermediates has also been achieved.

  N-Boc-5-膦基亚烷基-和N-Boc-5-二乙基膦酸酯-3-甲基-3-吡咯啉-2-酮在（5E）-和（5Z）-3-甲基-5的立体选择性合成中的应用检查了-亚苄基-3-吡咯啉-2-酮。还已经通过使用两种Wittig中间体实现了生长调节剂Ampullicin和Isoampullicin的立体选择性合成。
• Total Synthesis of (+)-Ampullicin and (+)-Isoampullicin:  Two Fungal Metabolites with Growth Regulatory Activity Isolated from <i>Ampulliferina</i> Sp. 27
  作者：Francisco A. Bermejo、Rosario Rico-Ferreira、S. Bamidele-Sanni、Santiago García-Granda

  DOI：10.1021/jo010527+

  日期：2001.12.1

  The total synthesis of the growth regulators (+)-ampullicin 1 and (+)-isoampullicin 2 from (R)(-)-carvone 5 was accomplished by application of an 18-step sequence with 4.5% overall yield. The crucial step of the synthetic strategy lies on the internal displacement of tosylate 13 by means of the lactone enolate. In this way, access was opened to the tricyclic core present in these biologically active sesquiterpenic amides. A Horner-Emmons reaction between the carbaldehyde 16 and the phosphonate 22 led us to the stereoselective preparation of (+)-ampullicin 1. Standard transformation of I into the thermodynamically more stable geometric isomer (+)-isoampullicin 2 was trivial. The absolute configuration of both amides was established by X-ray analysis of a sample of synthetic (+)-isoampullicin 2.