ethyl 1-(triisopropylsilyl)-3-pyrrolylglyoxalate | 87630-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 1-(triisopropylsilyl)-3-pyrrolylglyoxalate
• 英文别名: oxo-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-acetic acid ethyl ester；Oxo-(1-triisopropylsilyl-1H-pyrrol-3-YL)acetic acid ethyl ester；ethyl 2-oxo-2-[1-tri(propan-2-yl)silylpyrrol-3-yl]acetate
• CAS: 87630-37-3
• 化学式: C₁₇H₂₉NO₃Si
• 分子量: 323.508
• InChiKey: YVPLNLYLTVKXIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(triisopropylsilyl)-3-pyrrolylglyoxalate 在 potassium phosphate 、 copper(l) iodide 、 sodium hypophosphite 、 palladium on carbon 、 (1S,2S)-(+)-1,2-环己二胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 ethyl 2-[1-(6-indol-1-ylpyrazin-2-yl)pyrrol-3-yl]acetate
  参考文献：
  名称：

  Discovery and structure–activity relationship of 2,6-disubstituted pyrazines, potent and selective inhibitors of protein kinase CK2

  摘要：

  We report the discovery and structure-activity relationship of 2,6-disubstituted pyrazines, which are potent and selective CK2 inhibitors. Lead compound 1 was identified, and derivatives were prepared to develop potent inhibitory activity. As a result, we obtained compound 7, which was the smallest unit that retained potency. Then, introducing an aminoalkyl group at the 6-position of the indazole ring resulted in improved efficacy in both enzymatic and cell-based CK2 inhibition assays. Moreover, compound 13 showed selectivity against other kinases and in vivo efficacy in a rat nephritis model. These results show that 2,6-disubstituted pyrazines have potential as therapeutic agents for nephritis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.006
• 作为产物：
  描述：

  三异丙基氯硅烷 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 ethyl 1-(triisopropylsilyl)-3-pyrrolylglyoxalate
  参考文献：
  名称：

  β-取代的吡咯通过正三异丙基甲硅烷基吡咯的亲电取代。

  摘要：

  N-三异丙基甲硅烷基吡咯在C-3处经受主要或排他的动力学亲电取代，并且由此获得的化合物在与四丁基氟化铵进行甲硅烷基化后，以良好的总收率得到3-取代的吡咯。

  DOI：

  10.1016/s0040-4039(00)86011-6
• 作为试剂：
  描述：

  草酰氯单乙酯 、 吡啶 、 1-(三异丙基甲硅烷基)吡咯 、 碳酸氢钠 在 乙醚 、 magnesium sulfate 、 silica gel 、 ethyl 1-(triisopropylsilyl)-3-pyrrolylglyoxalate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以to give desired product oxo-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-acetic acid ethyl ester (22) (1.682 g, 58%) as a clear oil的产率得到ethyl 1-(triisopropylsilyl)-3-pyrrolylglyoxalate
  参考文献：
  名称：

  Pyridazinone compounds

  摘要：

  这项发明涉及吡啶并咪唑酮化合物以及包含这些化合物的药物组合物，这些化合物在治疗丙型肝炎病毒感染方面具有用处。

  公开号：

  US20080275032A1

文献信息

• β-substituted pyrroles via electrophilic substitution of n-triisopropylsilylpyrrole.
  作者：Joseph M Muchowski、Dennis R Solas

  DOI：10.1016/s0040-4039(00)86011-6

  日期：1983.1

  N-Triisopropylsilylpyrrole undergoes predominant or exclusive kinetic electrophilic substiution at C-3, and the compounds obtained thereby, upon desilylation with tetra--butylammonium fluoride, give 3-substituted pyrroles in good overall yields.

  N-三异丙基甲硅烷基吡咯在C-3处经受主要或排他的动力学亲电取代，并且由此获得的化合物在与四丁基氟化铵进行甲硅烷基化后，以良好的总收率得到3-取代的吡咯。
• WO2008/82725
  申请人：——

  公开号：——

  公开（公告）日：——
• N-(Triisopropylsilyl)pyrrole. A progenitor "par excellence" of 3-substituted pyrroles
  作者：Brian L. Bray、Peter H. Mathies、Reto Naef、Dennis R. Solas、Thomas T. Tidwell、Dean R. Artis、Joseph M. Muchowski

  DOI：10.1021/jo00313a019

  日期：1990.12

  A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the alpha-positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the beta-position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields. Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the alpha-positions is decelerated by a factor of > 10(4), vs pyrrole at the same sites, without affecting reactivity at the beta-positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents. This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of beta-substituted pyrroles, many of which would not be directly preparable from 1. TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions. This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound 5.
• BRAY, BRIAN L.;MATHIES, PETER H.;NAEF, RETO;SOLAS, DENNIS R.;TIDWELL, THO+, J. ORG. CHEM., 55,(1990) N6, C. 6317-6328
  作者：BRAY, BRIAN L.、MATHIES, PETER H.、NAEF, RETO、SOLAS, DENNIS R.、TIDWELL, THO+

  DOI：——

  日期：——
• MUCHOWSKI, J. M.;SOLAS, D. R., TETRAHEDRON LETT., 1983, 24, N 33, 3455-3456
  作者：MUCHOWSKI, J. M.、SOLAS, D. R.

  DOI：——

  日期：——