benzyl 2-methylfuran-3-carboxylate | 1334598-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-methylfuran-3-carboxylate
• 英文别名: Benzyl 2-methylfuran-3-carboxylate
• CAS: 1334598-35-4
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: VIDGKAJSORYSGN-UHFFFAOYSA-N

物化性质

• 沸点：
  309.5±27.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-methylfuran-3-carboxylate 在 4-二甲氨基吡啶 、 palladium on activated charcoal 、 水 、 氢气 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 60.0 ℃ 、100.0 kPa 条件下， 反应 51.75h， 生成 N-(5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-2-yl)-5-[3-(dimethylamino)-3-oxopropyl]-2-methylfuran-3-carboxamide
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

  摘要：

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.128
• 作为产物：
  描述：

  benzyl 2-acetyl-4-(tert-butylperoxy)-4-phenylbutanoate 在 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以64%的产率得到benzyl 2-methylfuran-3-carboxylate
  参考文献：
  名称：

  叔丁基过氧化物的重排用于建设多取代呋喃

  摘要：

  布朗斯台德酸催化的叔丁基过氧化物的重排提供了一种新的策略，可通过1,2-芳基迁移来构建2,3-二取代的呋喃。此外，叔丁基过氧化物也可以通过一系列碱催化的Kornblum-DelaMare重排和酸促进的Paal-Knorr反应转化为2,3,5-三取代或2,5-二取代的呋喃。

  DOI：

  10.1021/ol402509u

文献信息

• Rhodium-catalyzed synthesis of 2,3 – Disubstituted N -methoxy pyrroles and furans via [3+2] cycloaddition between metal carbenoids and activated olefins
  作者：Bharath Kumar Kuruba、Samuel Vasanthkumar、Lourdusamy Emmanuvel

  DOI：10.1016/j.tet.2017.04.007

  日期：2017.6

  the synthesis of 2-substituted N-alkoxy pyrrole 3-carboxylate and furan 3-carboxylate via Rh-catalyzed [3+2] cycloaddition between α-diazo oxime ether or α-diazo carbonyl compounds with vinyl equivalents in a one-pot process. We have demonstrated ethyl vinyl ether as well as vinyl acetate as vinyl equivalents and both were found to give excellent yields. We have also demonstrated the synthesis of N-alkoxy

  我们首次报道了通过α-重氮肟醚或具有乙烯基当量的α-重氮羰基化合物之间的Rh催化的[3 + 2]环加成反应合成2-取代的N-烷氧基吡咯3-羧酸盐和呋喃3-羧酸盐在一锅法过程中。我们已经证明乙基乙烯基醚以及乙酸乙烯酯作为乙烯基当量，并且发现两者均具有优异的产率。我们还证明了通过在低温下进行反应可以合成N-烷氧基二氢吡咯衍生物。
• The Rearrangement of <i>tert</i>-Butylperoxides for the Construction of Polysubstituted Furans
  作者：Xiaojian Zheng、Shenglin Lu、Zhiping Li

  DOI：10.1021/ol402509u

  日期：2013.11

  The Brønsted acid catalyzed rearrangement of tert-butyl peroxides provides a new strategy to construct 2,3-disubstituted furans via 1,2-aryl migration. In addition, tert-butyl peroxides could also be transformed into 2,3,5-trisubstituted or 2,5-disubstituted furans through a sequence of base-catalyzed Kornblum–DelaMare rearrangements and acid-promoted Paal–Knorr reactions.

  布朗斯台德酸催化的叔丁基过氧化物的重排提供了一种新的策略，可通过1,2-芳基迁移来构建2,3-二取代的呋喃。此外，叔丁基过氧化物也可以通过一系列碱催化的Kornblum-DelaMare重排和酸促进的Paal-Knorr反应转化为2,3,5-三取代或2,5-二取代的呋喃。
• Discovery and hit-to-lead optimization of novel allosteric glucokinase activators
  作者：Martin Lang、Markus H.-J. Seifert、Kristina K. Wolf、Andrea Aschenbrenner、Roland Baumgartner、Tanja Wieber、Viola Trentinaglia、Marcus Blisse、Nobumitsu Tajima、Tokuyuki Yamashita、Daniel Vitt、Hitoshi Noda

  DOI：10.1016/j.bmcl.2011.06.128

  日期：2011.9

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.