4-allyl-3-pyridinecarboxaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-allyl-3-pyridinecarboxaldehyde
• 英文别名: 4-prop-2-enylpyridine-3-carbaldehyde
• 化学式: C₉H₉NO
• 分子量: 147.177
• InChiKey: MUSULVDPALNXON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 4-allyl-3-pyridinecarboxaldehyde 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以86%的产率得到cis-1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyridine
  参考文献：
  名称：

  A one-pot assembly of 4-allyl-3-pyridinecarboxaldehyde. A new synthesis of 1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyrindine, an annulated nicotine analogue

  摘要：

  This paper describes a two-step synthesis of 1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyrindine, a conformationally constrained nicotine analogue. The target molecule was effectively assembled by an intramolecular azomethine ylide-alkene [3+2] cycloaddition. The cyclization precursor, 4-allyl-3-pyridinecarboxaldehyde, was formed efficaciously in a single step from 3-pyridinecarboxaldehyde via sequential in situ protection, ortho lithiation, cuprate formation, allylation, and deprotection. The cuprate formation plays a vital role in minimizing/eliminating the extent of multiple alkylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.069
• 作为产物：
  描述：

  3-吡啶甲醛 、 3-溴丙烯 在 正丁基锂 、 N,N,N'-三甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 以44%的产率得到4-allyl-3-pyridinecarboxaldehyde
  参考文献：
  名称：

  A one-pot assembly of 4-allyl-3-pyridinecarboxaldehyde. A new synthesis of 1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyrindine, an annulated nicotine analogue

  摘要：

  This paper describes a two-step synthesis of 1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyrindine, a conformationally constrained nicotine analogue. The target molecule was effectively assembled by an intramolecular azomethine ylide-alkene [3+2] cycloaddition. The cyclization precursor, 4-allyl-3-pyridinecarboxaldehyde, was formed efficaciously in a single step from 3-pyridinecarboxaldehyde via sequential in situ protection, ortho lithiation, cuprate formation, allylation, and deprotection. The cuprate formation plays a vital role in minimizing/eliminating the extent of multiple alkylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.069

文献信息

• Enantio‐ and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes
  作者：Anastassia Matviitsuk、Scott E. Denmark

  DOI：10.1002/anie.201906535

  日期：2019.9.2

  catalytic, enantio-, and diastereoselective formation of sulfenyl acetals bearing multiple stereogenic centers is reported. Alkenyl aldehydes undergo a chiral thiiranium ion initiated cascade starting with intramolecular capture by a formyl group and termination by capture with HFIP solvent. This method provides a one-pot synthesis of dihydropyran and 1,3-disubstituted isochroman acetals in good to excellent

  据报道，带有多个立体中心的亚硫基乙缩醛催化，对映体和非对映体选择性形成。烯基醛经历手性噻吩鎓离子引发的级联反应，首先通过甲酰基进行分子内捕获，然后通过用HFIP溶剂捕获而终止。该方法可以一锅法合成二氢吡喃和1,3-二取代的异苯并二氢吡喃缩醛，收率好至极好，非对映异构体含量高（高达> 99：1 dr），对映体控制（高达99：1 er）。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• BI-FUNCTIONAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Nuevolution A/S

  公开号：EP2558577A1

  公开（公告）日：2013-02-20
• BI-FUNCTINAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Gouliaev Alex Haahr

  公开号：US20130281324A1

  公开（公告）日：2013-10-24

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.
• [EN] BI-FUNCTIONAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES<br/>[FR] COMPLEXES BIFONCTIONNELS ET PROCÉDÉS DE FABRICATION ET D'UTILISATION DE TELS COMPLEXES
  申请人：NUEVOLUTION AS

  公开号：WO2011127933A1

  公开（公告）日：2011-10-20

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.