(2E)-1-(2-chloropyridin-3-yl)but-2-en-1-one | 1412404-32-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E)-1-(2-chloropyridin-3-yl)but-2-en-1-one
• 英文别名: (E)-1-(2-chloropyridin-3-yl)-2-buten-1-one；1-(2-chloropyridin-3-yl)but-2-en-1-one；(E)-1-(2-chloropyridin-3-yl)but-2-en-1-one
• CAS: 1412404-32-0
• 化学式: C₉H₈ClNO
• 分子量: 181.622
• InChiKey: ZBIQWWQBZDVKNF-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 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：

  (2E)-1-(2-chloropyridin-3-yl)but-2-en-1-one 在 sodium hydrosulfide monohydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以54%的产率得到2,3-dihydro-2-methyl-4H-thiopyrano[2,3-b]pyridin-4-one
  参考文献：
  名称：

  A Convenient Synthesis of 2,3-Dihydro-4H-thiopyrano[2,3-b]-, -[2,3-c]-, or -[3,2-c]pyridin-4-ones by the Reaction of the Corresponding 1-(Chloropyridinyl)alk-2-en-1-ones with NaSH

  摘要：

  Abstract2,3‐Dihydro‐4H‐thiopyrano[2,3‐b]pyridin‐4‐ones 4 were prepared by a three‐step sequence from commercially available 2‐chloropyridine (1). Thus, successive treatment of 1 with iPr2NLi (LDA) and α,β‐unsaturated aldehydes gave 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ols 2, which were oxidized with MnO2 to 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ones 3. The reactions of 3 with NaSH⋅n H2O proceeded smoothly at 0° in DMF to provide the desired thiopyranopyridinones. Similarly, 2,3‐dihydro‐4H‐thiopyrano[2,3‐c]pyridin‐4‐ones 8 and 2,3‐dihydro‐4H‐thiopyrano[3,2‐c]pyridin‐4‐ones 12 were obtained starting from 3‐chloropyridine (5) and 4‐chloropyridine (9), respectively.

  DOI：

  10.1002/hlca.201200543
• 作为产物：
  描述：

  2-氯-3-吡啶甲醛 在 manganese(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 (2E)-1-(2-chloropyridin-3-yl)but-2-en-1-one
  参考文献：
  名称：

  通过串联Michael–S N Ar环化反应生成1-烷基-和（±）-1,2-二烷基-2,3-二氢-1,8-萘啶-4（1 H）-ones

  摘要：

  一种串联迈克尔-S Ñ的Ar环反应已被开发用于1-烷基的合成和（±）-1,2-二烷基-2,3-二氢-1,8-二氮杂萘-4（1H） -酮。1-（2-氯吡啶-3-基）丙-2-烯-1-酮（R = H）或（E或Z）-1-（2-氯吡啶-3-基）丁-2-烯的处理在DMF中在50°C的条件下，用R'NH 2在DMF中的-1- 1（R = CH 3）提供2,3-二氢-1,8-萘啶-4（1H）-1 ，产率为65-85％。机理研究表明，反应序列是由迈克尔加成到侧链烯酮上而引发的。

  DOI：

  10.1021/jo3018632

文献信息

• FUSED PIPERIDINE COMPOUND AND PHARMACEUTICAL CONTAINING SAME
  申请人：Ashikawa Masanori

  公开号：US20120108581A1

  公开（公告）日：2012-05-03

  The present invention provides a low molecular weight compound having EPO production-promoting action and/or hemoglobin production-promoting action. The present invention relates to a fused piperidine compound represented by the following general formula (1): (wherein, ring A represents a C 10-14 aryl group or 5- to 10-membered heterocyclic group, X represents N—R 7 , a sulfur atom or an oxygen atom, R 1 , R 2 , R 2′ , R 3 and R 3′ independently represent a hydrogen atom, C 1-6 alkyl group or C 3-6 cycloalkyl group, and R 4 , R 5 and R 6 independently represent a hydrogen atom or halogen atom), or a salt thereof, or a solvate thereof.

  本发明提供了一种低分子量化合物，具有促进EPO产生和/或促进血红蛋白产生的作用。本发明涉及一种融合哌啶化合物，其表示为以下通式（1）： （其中，环A表示C10-14芳基或5-至10元杂环基，X表示N-R7，硫原子或氧原子，R1、R2、R2'、R3和R3'独立地表示氢原子、C1-6烷基或C3-6环烷基，而R4、R5和R6独立地表示氢原子或卤素原子），或其盐或溶剂化物。
• FUSED PIPERIDINE COMPOUND AND PHARMACEUTICAL AGENT COMPRISING SAME
  申请人：Kowa Company, Ltd.

  公开号：EP2412710A1

  公开（公告）日：2012-02-01

  The present invention provides a low molecular weight compound having EPO production-promoting action and/or hemoglobin production-promoting action. The present invention relates to a fused piperidine compound represented by the following general formula (1): (wherein, ring A represents a C10-14 aryl group or 5- to 10-membered heterocyclic group, ring B represents a C6-14 alkyl group, X represents N-R7, a sulfur atom or an oxygen atom, R1, R2, R2', R3 and R3' independently represent a hydrogen atom, C1-6 alkyl group or C3-6 cycloalkyl group, and R4, R5 and R6 independently represent a hydrogen atom or halogen atom), or a salt thereof, or a solvate thereof.

  本发明提供了一种具有促进EPO生成作用和/或促进血红蛋白生成作用的低分子量化合物。本发明涉及一种由以下通式（1）代表的融合哌啶化合物： (其中，环A代表C10-14芳基或5-10元杂环基，环B代表C6-14烷基，X代表N-R7、硫原子或氧原子，R1、R2、R2'、R3和R3'独立地代表氢原子、C1-6烷基或C3-6环烷基，R4、R5和R6独立地代表氢原子或卤素原子），或其盐，或其溶液。
• US8604030B2
  申请人：——

  公开号：US8604030B2

  公开（公告）日：2013-12-10
• A Convenient Synthesis of 2,3-Dihydro-4<i>H</i>-thiopyrano[2,3-<i>b</i>]-, -[2,3-<i>c</i>]-, or -[3,2-<i>c</i>]pyridin-4-ones by the Reaction of the Corresponding 1-(Chloropyridinyl)alk-2-en-1-ones with NaSH
  作者：Kazuhiro Kobayashi、Ayumi Imaoka

  DOI：10.1002/hlca.201200543

  日期：2013.4

  Abstract2,3‐Dihydro‐4H‐thiopyrano[2,3‐b]pyridin‐4‐ones 4 were prepared by a three‐step sequence from commercially available 2‐chloropyridine (1). Thus, successive treatment of 1 with iPr2NLi (LDA) and α,β‐unsaturated aldehydes gave 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ols 2, which were oxidized with MnO2 to 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ones 3. The reactions of 3 with NaSH⋅n H2O proceeded smoothly at 0° in DMF to provide the desired thiopyranopyridinones. Similarly, 2,3‐dihydro‐4H‐thiopyrano[2,3‐c]pyridin‐4‐ones 8 and 2,3‐dihydro‐4H‐thiopyrano[3,2‐c]pyridin‐4‐ones 12 were obtained starting from 3‐chloropyridine (5) and 4‐chloropyridine (9), respectively.
• 1-Alkyl- and (±)-1,2-Dialkyl-2,3-dihydro-1,8-naphthyridin-4(1<i>H</i>)-ones by a Tandem Michael–S_NAr Annulation Reaction
  作者：Richard A. Bunce、Scott T. Squires、Baskar Nammalwar

  DOI：10.1021/jo3018632

  日期：2013.3.1

  A tandem Michael–SNAr annulation reaction has been developed for the synthesis of 1-alkyl and (±)-1,2-dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones. Treatment of 1-(2-chloropyridin-3-yl)prop-2-en-1-one (R = H) or (E or Z)-1-(2-chloropyridin-3-yl)but-2-en-1-one (R = CH3) with R′NH2 in DMF at 50 °C for 24 h provides 2,3-dihydro-1,8-naphthyridin-4(1H)-ones in 65–85% yields. Mechanistic studies suggest

  一种串联迈克尔-S Ñ的Ar环反应已被开发用于1-烷基的合成和（±）-1,2-二烷基-2,3-二氢-1,8-二氮杂萘-4（1H） -酮。1-（2-氯吡啶-3-基）丙-2-烯-1-酮（R = H）或（E或Z）-1-（2-氯吡啶-3-基）丁-2-烯的处理在DMF中在50°C的条件下，用R'NH 2在DMF中的-1- 1（R = CH 3）提供2,3-二氢-1,8-萘啶-4（1H）-1 ，产率为65-85％。机理研究表明，反应序列是由迈克尔加成到侧链烯酮上而引发的。