(E)-ethyl 2-ethanoyl-4-iodo-2-methyl-3-phenylbut-3-enoate | 1016892-99-1

• 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: (E)-ethyl 2-ethanoyl-4-iodo-2-methyl-3-phenylbut-3-enoate
• 英文别名: ethyl (E)-2-acetyl-4-iodo-2-methyl-3-phenylbut-3-enoate
• CAS: 1016892-99-1
• 化学式: C₁₅H₁₇IO₃
• 分子量: 372.203
• InChiKey: MTGIEYXLJILWBH-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-ethanoyl-4-iodo-2-methyl-3-phenylbut-3-enoate 、 苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 以95%的产率得到(E)-ethyl 2-ethanoyl-2-methyl-3,4-diphenylbut-3-enoate
  参考文献：
  名称：

  Stereoselective Synthesis of Trisubstituted E-Iodoalkenes by Indium-Catalyzed syn-Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes

  摘要：

  Indium-catalyzed addition of 1,3-dicarbonyl compounds to 1-iodo-1-alkynes takes place exclusively in a syn-fashion to produce E-iodoalkenes. The iodine atom serves both as an activating group and as a group that controls the regioselectivity of the addition. The E-alkenyl iodide product can be further derivatized using either a one-pot or a two-pot procedure into trisubstituted olefins in high overall yield with retention of the stereochemistry.

  DOI：

  10.1021/ol800105r
• 作为产物：
  描述：

  2-甲基乙酰乙酸乙酯 、 (碘乙炔基)苯 在 indium(III) tris[bis(trifluoromethanesulfonyl)amide] 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以92%的产率得到(E)-ethyl 2-ethanoyl-4-iodo-2-methyl-3-phenylbut-3-enoate
  参考文献：
  名称：

  Stereoselective Synthesis of Trisubstituted E-Iodoalkenes by Indium-Catalyzed syn-Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes

  摘要：

  Indium-catalyzed addition of 1,3-dicarbonyl compounds to 1-iodo-1-alkynes takes place exclusively in a syn-fashion to produce E-iodoalkenes. The iodine atom serves both as an activating group and as a group that controls the regioselectivity of the addition. The E-alkenyl iodide product can be further derivatized using either a one-pot or a two-pot procedure into trisubstituted olefins in high overall yield with retention of the stereochemistry.

  DOI：

  10.1021/ol800105r

文献信息

• Stereoselective Synthesis of Trisubstituted <i>E</i>-Iodoalkenes by Indium-Catalyzed <i>syn</i>-Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes
  作者：Hayato Tsuji、Taisuke Fujimoto、Kohei Endo、Masaharu Nakamura、Eiichi Nakamura

  DOI：10.1021/ol800105r

  日期：2008.3.1

  Indium-catalyzed addition of 1,3-dicarbonyl compounds to 1-iodo-1-alkynes takes place exclusively in a syn-fashion to produce E-iodoalkenes. The iodine atom serves both as an activating group and as a group that controls the regioselectivity of the addition. The E-alkenyl iodide product can be further derivatized using either a one-pot or a two-pot procedure into trisubstituted olefins in high overall yield with retention of the stereochemistry.