isopropyl 1-(tert-butyloxycarbonyl)-2-benzoyl-2,5-dihydropyrrole-2-carboxylate | 263408-02-2

• 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-benzoyl-2,5-dihydropyrrole-2-carboxylate
• 英文别名: 1-O-tert-butyl 5-O-propan-2-yl 5-benzoyl-2H-pyrrole-1,5-dicarboxylate
• CAS: 263408-02-2
• 化学式: C₂₀H₂₅NO₅
• 分子量: 359.422
• InChiKey: WNUAYOGPKNSNEW-UHFFFAOYSA-N

物化性质

• 沸点：
  452.6±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  isopropyl 1-(tert-butyloxycarbonyl)-2-benzoyl-2,5-dihydropyrrole-2-carboxylate 在 cerium(III) chloride sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 生成 (1'RS,2SR)-isopropyl 1-(tert-butyloxycarbonyl)-2-[1'-hydroxy-1'-phenyl-methyl]-2,5-dihydropyrrole-2-carboxylate 、 (1'RS,2RS)-isopropyl 1-(tert-butyloxycarbonyl)-2-[1'-hydroxy-1'-phenyl-methyl]-2,5-dihydropyrrole-2-carboxylate
  参考文献：
  名称：

  Reductive aldol reactions on aromatic heterocycles

  摘要：

  The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02224-8
• 作为产物：
  描述：

  isopropyl pyrrole-2-carboxylate 在 水 、 lithium 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 为溶剂， 生成 isopropyl 1-(tert-butyloxycarbonyl)-2-benzoyl-2,5-dihydropyrrole-2-carboxylate
  参考文献：
  名称：

  Reductive aldol reactions on aromatic heterocycles

  摘要：

  The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02224-8

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.