isopropyl 1-(tert-butyloxycarbonyl)-2,5-dihydropyrrole-2-carboxylate | 444814-96-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: isopropyl 1-(tert-butyloxycarbonyl)-2,5-dihydropyrrole-2-carboxylate
• 英文别名: 1-O-tert-butyl 2-O-propan-2-yl 2,5-dihydropyrrole-1,2-dicarboxylate
• CAS: 444814-96-4
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: NDESIPASSXNMQR-UHFFFAOYSA-N

物化性质

• 沸点：
  315.6±42.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl 1-(tert-butyloxycarbonyl)-2,5-dihydropyrrole-2-carboxylate 在 锂硼氢 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 tert-butyl 2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  3-(2,5-Dihydro-1H-pyrrol-2-ylmethoxy)pyridines: synthesis and analgesic activity

  摘要：

  We disclose an efficient procedure for the preparation of ethers of 2-substituted 2-hydroxymethylpyrroline and of 2-aminomethyl-3-pyrrolines, involving, as a key step, formation and nucleophilic ring opening of a cyclic sulfamidate. Several new analogs of epibatidine (1) and tebanicline (ABT-594, 2) were prepared and tested for analgesic activity in the mouse formalin model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.058
• 作为产物：
  描述：

  isopropyl 1-(tert-butoxycarbonyl)pyrrole-2-carboxylate 在 正溴丁烷 bis(methoxyethyl)-amine 、 di(tert-butyl)-biphenyl 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以62%的产率得到isopropyl 1-(tert-butyloxycarbonyl)-2,5-dihydropyrrole-2-carboxylate
  参考文献：
  名称：

  使用二叔丁基联苯锂（LiDBB）无氨部分还原芳族化合物。

  摘要：

  描述了在无氨条件下一系列杂环和碳环芳族化合物的还原。通过使用LiDBB作为电子源，使用双（甲氧基乙基）胺（BMEA）作为质子化剂，使用THF作为溶剂，我们能够更通常地在Birch型条件下完成还原反应。此外，通过还原系统对不能在氨中成功使用的反应性亲电试剂的耐受性，进一步增强了这些条件的使用。

  DOI：

  10.1021/jo0257593

文献信息

• Ammonia Free Partial Reduction of Aromatic Compounds Using Lithium Di-<i>tert</i>-butylbiphenyl (LiDBB)
  作者：Timothy J. Donohoe、David House

  DOI：10.1021/jo0257593

  日期：2002.7.1

  The reduction of a series of hetero- and carbocyclic aromatic compounds under ammonia free conditions is described. By using LiDBB as a source of electrons, bis(methoxyethyl)amine (BMEA) as a protonating agent, and THF as a solvent, we were able to accomplish reductions more usually performed under Birch type conditions. Moreover, the use of these conditions was further enhanced by the tolerance of

  描述了在无氨条件下一系列杂环和碳环芳族化合物的还原。通过使用LiDBB作为电子源，使用双（甲氧基乙基）胺（BMEA）作为质子化剂，使用THF作为溶剂，我们能够更通常地在Birch型条件下完成还原反应。此外，通过还原系统对不能在氨中成功使用的反应性亲电试剂的耐受性，进一步增强了这些条件的使用。
• The partial reduction of heterocycles: an alternative to the Birch reduction
  作者：Timothy J Donohoe、Rakesh R Harji、Rick P.C Cousins

  DOI：10.1016/s0040-4039(99)02315-1

  日期：2000.2

  The partial reduction of a series of heterocycles in THF is described. By adding amine 3 as a proton source and naphthalene as an electron carrier, we were able to produce reductively alkylated pyrrolines and dihydrofurans in moderate to good yields. This reaction does not require liquid ammonia as a solvent, which may have interesting ramifications for large-scale synthesis. Moreover, we were also able to quench the reduction reactions with an acid chloride so performing a reductive acylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 3-(2,5-Dihydro-1H-pyrrol-2-ylmethoxy)pyridines: synthesis and analgesic activity
  作者：Ivan L. Baraznenok、Emma Jonsson、Alf Claesson

  DOI：10.1016/j.bmcl.2005.01.058

  日期：2005.3

  We disclose an efficient procedure for the preparation of ethers of 2-substituted 2-hydroxymethylpyrroline and of 2-aminomethyl-3-pyrrolines, involving, as a key step, formation and nucleophilic ring opening of a cyclic sulfamidate. Several new analogs of epibatidine (1) and tebanicline (ABT-594, 2) were prepared and tested for analgesic activity in the mouse formalin model. (c) 2005 Elsevier Ltd. All rights reserved.