5-(4-chloro-phenyl)-2-pyridin-2-yl-pent-4-ynoic acid ethyl ester

• 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: 5-(4-chloro-phenyl)-2-pyridin-2-yl-pent-4-ynoic acid ethyl ester
• 英文别名: Ethyl 5-(4-chlorophenyl)-2-pyridin-2-ylpent-4-ynoate
• 化学式: C₁₈H₁₆ClNO₂
• 分子量: 313.784
• InChiKey: QGZOSQDZHCZEMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chloro-phenyl)-2-pyridin-2-yl-pent-4-ynoic acid ethyl ester 在 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以77%的产率得到ethyl 3-(4-chlorobenzoyl)indolizine-1-carboxylate
  参考文献：
  名称：

  A novel approach to 3-acylated indolizine structures via iodine-mediated hydrative cyclization

  摘要：

  We have discovered a new route to 3-acylated indolizine structures via iodine-mediated hydrative cyclization. Reaction mechanism is proposed for this novel transformation, which involves a 5-exo-dig iodocyclization, deprotonation, incorporation of another iodo group, deprotonation, and subsequent replacement of the diiodo group by H2O. Various 3-acylated indolizine derivatives were obtained using this mild procedure in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.101
• 作为产物：
  描述：

  2-吡啶乙酸乙酯 、 1-(3-bromoprop-1-yn-1-yl)-4-chlorobenzene 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 5-(4-chloro-phenyl)-2-pyridin-2-yl-pent-4-ynoic acid ethyl ester
  参考文献：
  名称：

  A novel approach to 3-acylated indolizine structures via iodine-mediated hydrative cyclization

  摘要：

  We have discovered a new route to 3-acylated indolizine structures via iodine-mediated hydrative cyclization. Reaction mechanism is proposed for this novel transformation, which involves a 5-exo-dig iodocyclization, deprotonation, incorporation of another iodo group, deprotonation, and subsequent replacement of the diiodo group by H2O. Various 3-acylated indolizine derivatives were obtained using this mild procedure in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.101