isopropyl 1-(tert-butoxycarbonyl)pyrrole-2-carboxylate | 183998-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: isopropyl 1-(tert-butoxycarbonyl)pyrrole-2-carboxylate
• 英文别名: isopropyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate；1-tert-Butyl 2-isopropyl 1H-pyrrole-1,2-dicarboxylate；1-O-tert-butyl 2-O-propan-2-yl pyrrole-1,2-dicarboxylate
• CAS: 183998-34-7
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: GUHDGAWTPGYTRG-UHFFFAOYSA-N

物化性质

• 沸点：
  329.1±34.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl 1-(tert-butoxycarbonyl)pyrrole-2-carboxylate 在 锂硼氢 、 氨 、 sodium 作用下， 以 四氢呋喃 、 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：

  吡咯-2-羧酸 在 氢氧化钾 、 草酰氯 、 sodium hydride 作用下， 生成 isopropyl 1-(tert-butoxycarbonyl)pyrrole-2-carboxylate
  参考文献：
  名称：

  Birch Reduction of Electron-Deficient Pyrroles

  摘要：

  DOI：

  10.1021/jo961688u

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。
• Reduction of electron-deficient pyrroles using group I and II metals in ammonia
  作者：Timothy J. Donohoe、Paul M. Guyo、Roy L. Beddoes、Madeleine Helliwell

  DOI：10.1039/a707661d

  日期：——

  The preparation and Birch reduction of a series of electron-deficient pyrroles is described. This methodology allows the synthesis of a variety of C-2 substituted 3-pyrrolines‡ in good to excellent yields. The role of various activating groups (amide, ester, carbamate and urea) has been examined with regard to both stability under the Birch conditions and ease of deprotection after reduction. In addition, we discovered that the 3-pyrroline skeleton can be oxidised at C-5 with chromium trioxide–3,5-dimethylpyrazole to form the 3-pyrrolin-2-one nucleus. The identity of the Birch reduced products and also of the oxidised 3-pyrrolin-2-ones has been confirmed by X-ray crystallography on two derivatives.

  描述了一系列缺电子吡咯的制备和伯奇还原。这种方法允许以良至优秀的产率合成各种C-2取代的3-吡咯啉。研究了不同的活化基团（酰胺、酯、氨基甲酸酯和脲）在伯奇反应条件下的稳定性以及还原后去保护的难易程度。此外，我们发现3-吡咯啉骨架可以用三氧化铬和3,5-二甲基吡唑在C-5位氧化，形成3-吡咯啉-2-酮核。通过对两个衍生物的X射线晶体学确定了伯奇还原产物以及氧化的3-吡咯啉-2-酮的身份。
• Rearrangement of pyrrolines derived from the Birch reduction of electron-deficient pyrroles: radical ring-expansion to substituted tetrahydropyridines
  作者：Peter G. Turner、Timothy J. Donohoe、Rick P. C. Cousins

  DOI：10.1039/b404002c

  日期：——

  Access to the synthetically important tetrahydropyridine motif has been achieved by radical rearrangement of pyrrolines obtained from the Birch reduction of electron-deficient pyrroles.

  通过对从电子缺陷吡咯的Birch还原中获得的吡咯啉进行自由基重排，实现了对合成重要的四氢吡啶基团的获取。
• Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocyclesThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.
  作者：Timothy J. Donohoe、David House、K. W. Ace

  DOI：10.1039/b306937k

  日期：——

  The reductive aldol reaction of electron deficient aromatic compounds has been investigated and found to be a viable method for carbon–carbon bond formation. Reductions under ammonia and ammonia-free conditions were both capable of facilitating the aldol reaction although the latter showed more scope for reaction with enolisable aldehydes. Moreover, reduction under ammonia-free conditions allowed the addition of Lewis acids which improved stereoselectivity to favour the anti stereoisomer. Production of the syn diastereoisomer was possible through either one of two different protocols performed after partial reduction was complete. While the main emphasis of this paper concerns the reductive aldol reaction of electron deficient pyrroles, it was also shown that both benzenoid and furan aromatic compounds were amenable to such reducing conditions.

  研究发现，缺电子芳香化合物的还原醛醇反应是碳-碳键形成的一种可行方法。氨和无氨条件下的还原反应都能促进醛醇反应，但后者在与可烯化的醛反应中表现出更大的空间。此外，在无氨条件下还原可以加入路易斯酸，从而提高立体选择性，有利于反立体异构体。在部分还原完成后，可以通过两种不同方案中的一种来生产合成非对映异构体。本文的主要重点是缺电子吡咯的还原性醛醇反应，但同时也证明了苯类和呋喃类芳香化合物也适用于这种还原条件。
• Reductive aldol reactions on aromatic heterocycles
  作者：Timothy J Donohoe、Karl W Ace、Paul M Guyo、Madeleine Helliwell、Jeffrey McKenna

  DOI：10.1016/s0040-4039(99)02224-8

  日期：2000.2

  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.