N-benzyl-3,4-dimethoxypyrrole | 220279-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-3,4-dimethoxypyrrole
• 英文别名: 1-Benzyl-3,4-dimethoxy-1H-pyrrole；1-benzyl-3,4-dimethoxypyrrole
• CAS: 220279-97-0
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: WCXAMLUNRQVPBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-3,4-dimethoxypyrrole 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以94%的产率得到3,4-二甲氧基吡咯
  参考文献：
  名称：

  A Short and Efficient Synthesis of 3,4-Dialkoxypyrroles

  摘要：

  3,4-二烷氧基吡咯通过四个步骤从商业可得的2,5-二甲氧基-2,5-二氢呋喃（1）获得。首先，二氢呋喃1被KMnO4氧化成二醇2，然后对其进行双烷基化反应生成3a-d。通过与原位生成的双醛与一级胺反应，得到了N取代的双烷氧基吡咯4a-m。N-苄基-3,4-二烷氧基吡咯和N-烯丙基-双烷氧基吡咯在液氨中被钠裂解，获得了N-未取代的双烷氧基吡咯5a-c，整体产率良好。

  DOI：

  10.1055/s-1999-3687
• 作为产物：
  描述：

  (+/-)-2ξ,3r,4c,5ξ-Tetramethoxy-tetrahydro-furan 在 硫酸 、 水 、 sodium acetate 作用下， 以 氯仿 、 水 为溶剂， 反应 20.5h， 生成 N-benzyl-3,4-dimethoxypyrrole
  参考文献：
  名称：

  A Short and Efficient Synthesis of 3,4-Dialkoxypyrroles

  摘要：

  3,4-二烷氧基吡咯通过四个步骤从商业可得的2,5-二甲氧基-2,5-二氢呋喃（1）获得。首先，二氢呋喃1被KMnO4氧化成二醇2，然后对其进行双烷基化反应生成3a-d。通过与原位生成的双醛与一级胺反应，得到了N取代的双烷氧基吡咯4a-m。N-苄基-3,4-二烷氧基吡咯和N-烯丙基-双烷氧基吡咯在液氨中被钠裂解，获得了N-未取代的双烷氧基吡咯5a-c，整体产率良好。

  DOI：

  10.1055/s-1999-3687

文献信息

• N-Substituted 3,4-Alkylenedioxypyrroles, Ester Substituted Dihydroxypyrroles and Methods for Synthesis of These Pyrroles
  申请人：Reynolds John R.

  公开号：US20090149661A1

  公开（公告）日：2009-06-11

  A family of N-substituted 3,4-alkylenedioxypyrrole includes monomers for of formula (I) electropolymerization to conjugated polymers and key intermediates for the preparation of the monomers. The preparation of the //-substituted 3,4-alkylenedioxypyrroles is carried out via a synthetic intermediate, an ester substituted dihydroxypyrrole. The synthetic method to prepare the //-substituted 3,4-alkylenedioxypyrrole intermediates and ultimately the N-substituted 3,4-alkylenedioxypyrrole monomers begins with a reaction to form the ester substituted dihydroxypyrrole.

  一种N-取代的3,4-烷基二氧杂吡咯家族包括式（I）的单体，用于电聚合制备共轭聚合物以及制备单体的关键中间体。N-取代的3,4-烷基二氧杂吡咯的制备通过合成中间体，酯基取代的二羟基吡咯酮进行。制备N-取代的3,4-烷基二氧杂吡咯单体的合成方法始于形成酯基取代的二羟基吡咯酮的反应。
• β-Octamethoxyporphycenes
  作者：Anup Rana、Pradeepta K. Panda

  DOI：10.1021/ol403068j

  日期：2014.1.3

  Porphycene with eight methoxy substituents at its beta-positions was synthesized for the first time in three steps from 3,4-dimethoxypyrrole. The presence of methoxy groups increases its hydrophilicity as evident from their increased solubility in methanol. Among its metallo-derivatives, the Pd(II)-complex displays efficient singlet oxygen quantum yield (73%) and hence can be a potentially good photosensitizer for photo-oxidation, DNA cleavage, and photodynamic therapy (PDT).
• β-Decamethoxysapphyrin and Its <i>N</i>-Benzyl Analogue
  作者：Anup Rana、B. Sathish Kumar、Pradeepta K. Panda

  DOI：10.1021/acs.orglett.5b01306

  日期：2015.6.19

  The synthesis of a highly electron-rich decamethoxysapphyrin and its 27-N-benzyl analogue is reported for the first time. The effects of beta-methoxy and 27-N-benzyl substitution on structure, anion binding, absorption, and electrochemical properties were explored in detail. Upon 27-N-benzyl substitution, counteranion-induced structural deformation arises in the diprotonated state, which could be clearly noticed both in solution H-1 NMR study and solid-state structural analysis. This type of anion-induced structural deformation is noted for the first time in beta-substituted sapphyrins. Further, the free base sapphyrins generate singlet oxygen with moderate efficiency (similar to 42%); hence, they may act as good photosensitizers.
• N-SUBSTITUTED 3,4-ALKYLENEDIOXYPYRROLES, ESTER SUBSTITUTED DIHYDROXYPYRROLES AND METHODS FOR SYNTHESIS OF THESE PYRROLES
  申请人：University of Florida Research Foundation, Incorporated

  公开号：EP1931630B1

  公开（公告）日：2010-05-12
• A Short and Efficient Synthesis of 3,4-Dialkoxypyrroles
  作者：Andreas Merz、Thomas Meyer

  DOI：10.1055/s-1999-3687

  日期：——

  3,4-Dialkoxypyrroles are obtained in four steps from commercially available 2,5-dimethoxy-2,5-dihydrofuran (1). The dihydrofuran 1 is first oxidized by KMnO4 to the diol 2 which is bisalkylated to 3a-d. Reaction of the in situ generated dialdehydes with a primary amine affords the N-substituted dialkoxypyrroles 4a-m. N-Benzyl-3,4-dialkoxypyrroles and N-allyl-dialkoxypyrroles are cleaved by sodium in liquid ammonia affording N-unsubstituted dialkoxypyrroles 5a-c in good overall yield.

  3,4-二烷氧基吡咯通过四个步骤从商业可得的2,5-二甲氧基-2,5-二氢呋喃（1）获得。首先，二氢呋喃1被KMnO4氧化成二醇2，然后对其进行双烷基化反应生成3a-d。通过与原位生成的双醛与一级胺反应，得到了N取代的双烷氧基吡咯4a-m。N-苄基-3,4-二烷氧基吡咯和N-烯丙基-双烷氧基吡咯在液氨中被钠裂解，获得了N-未取代的双烷氧基吡咯5a-c，整体产率良好。