1H-吡咯-1,2-二羧酸,2,5-二氢-2-甲基-,1-(1,1-二甲基乙基)2-(1-甲基乙基)酯 | 183998-35-8

• 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
• 中文名称: 1H-吡咯-1,2-二羧酸,2,5-二氢-2-甲基-,1-(1,1-二甲基乙基)2-(1-甲基乙基)酯
• 英文名称: isopropyl 1-(tert-butoxycarbonyl)-2-methyl-2,5-dihydro-1H-pyrrole-2-carboxylate
• 英文别名: isopropyl 1-(tert-butyloxycarbonyl)-2-methyl-2,5-dihydropyrrole-2-carboxylate；1-O-tert-butyl 5-O-propan-2-yl 5-methyl-2H-pyrrole-1,5-dicarboxylate
• CAS: 183998-35-8
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: LKGNITLYFDOZED-UHFFFAOYSA-N

物化性质

• 沸点：
  321.6±42.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  1H-吡咯-1,2-二羧酸,2,5-二氢-2-甲基-,1-(1,1-二甲基乙基)2-(1-甲基乙基)酯 在 lithium aluminium tetrahydride 、 甲烷磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2-Methyl-2,5-dihydro-1H-pyrrol-2-yl)methanol
  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 、 sodium hydride 作用下， 生成 1H-吡咯-1,2-二羧酸,2,5-二氢-2-甲基-,1-(1,1-二甲基乙基)2-(1-甲基乙基)酯
  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。
• 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.