(2E)-1-(2-chloropyridin-3-yl)but-2-en-1-ol | 1412404-25-1

• 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: (2E)-1-(2-chloropyridin-3-yl)but-2-en-1-ol
• 英文别名: (E)-1-(2-chloropyridin-3-yl)but-2-en-1-ol
• CAS: 1412404-25-1
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: YZZCFXKCXAYDKQ-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 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-ol 在 manganese(IV) oxide 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以73%的产率得到(2E)-1-(2-chloropyridin-3-yl)but-2-en-1-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-氯吡啶 、 巴豆醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以52%的产率得到(2E)-1-(2-chloropyridin-3-yl)but-2-en-1-ol
  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

文献信息

• 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.