methyl (E)-2-ethylseleno-3-chloro-3-phenylacrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-2-ethylseleno-3-chloro-3-phenylacrylate
• 英文别名: methyl (E)-3-chloro-2-ethylselanyl-3-phenylprop-2-enoate
• 化学式: C₁₂H₁₃ClO₂Se
• 分子量: 303.647
• InChiKey: IIQQUHYQQHKXDE-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-ethylseleno-3-chloro-3-phenylacrylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以76%的产率得到3-苯基丙-2-烯-1-醇
  参考文献：
  名称：

  Unique Regio- and Stereoselectivity in Pd-Catalyzed Chlorocarbonylation Reaction of 2-Phenylethynyl Selenides and 2-Alkylethynyl Selenides. Highly Stereoselective Synthesis of 2-Seleno-3-chloroacrylates

  摘要：

  Regio- and stereoselectivity in the chloropalladation carbonylation reaction of different acetylenic selenides in the presence of 0.05 equiv of PdCl2 and 3 equiv of cupric chloride under 1 atm of carbon monoxide affording 2-seleno-3-chloroacrylates were investigated. Opposite stereoselectivities were observed with 2-phenylethynyl selenides and 8-alkylethynyl selenides the reactions of 2-phenylethynyl selenides afforded (E)-2-seleno-3-chloro-3-phenylacrylates, while the reactions of 8-alkyl-ethynyl selenides gave (Z)-2-seleno-3-chloro-3-alkylacrylates. A chloropalladation carbonylation mechanism for this reaction was proposed. The regio- and stereoselective chloropalladation of the carbon-carbon triple bond in acetylenic selenides affords 1-enylpalladium intermediates, in which : the palladium atom connects with the carbon atom bonding with the selenium atom. Carbonylation in the presence of an alcohol affords 2-seleno-3-chloroacrylates.

  DOI：

  10.1021/jo0006977
• 作为产物：
  描述：

  甲醇 、 一氧化碳 、 2-phenylethynyl ethyl selenide 在 copper dichloride 、 palladium dichloride 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 [(E)-1,2-dichloro-2-ethylselanylethenyl]benzene 、 methyl (Z)-2-ethylseleno-3-chloro-3-phenylacrylate 、 methyl (E)-2-ethylseleno-3-chloro-3-phenylacrylate
  参考文献：
  名称：

  Unique Regio- and Stereoselectivity in Pd-Catalyzed Chlorocarbonylation Reaction of 2-Phenylethynyl Selenides and 2-Alkylethynyl Selenides. Highly Stereoselective Synthesis of 2-Seleno-3-chloroacrylates

  摘要：

  Regio- and stereoselectivity in the chloropalladation carbonylation reaction of different acetylenic selenides in the presence of 0.05 equiv of PdCl2 and 3 equiv of cupric chloride under 1 atm of carbon monoxide affording 2-seleno-3-chloroacrylates were investigated. Opposite stereoselectivities were observed with 2-phenylethynyl selenides and 8-alkylethynyl selenides the reactions of 2-phenylethynyl selenides afforded (E)-2-seleno-3-chloro-3-phenylacrylates, while the reactions of 8-alkyl-ethynyl selenides gave (Z)-2-seleno-3-chloro-3-alkylacrylates. A chloropalladation carbonylation mechanism for this reaction was proposed. The regio- and stereoselective chloropalladation of the carbon-carbon triple bond in acetylenic selenides affords 1-enylpalladium intermediates, in which : the palladium atom connects with the carbon atom bonding with the selenium atom. Carbonylation in the presence of an alcohol affords 2-seleno-3-chloroacrylates.

  DOI：

  10.1021/jo0006977

文献信息

• Unique Regio- and Stereoselectivity in Pd-Catalyzed Chlorocarbonylation Reaction of 2-Phenylethynyl Selenides and 2-Alkylethynyl Selenides. Highly Stereoselective Synthesis of 2-Seleno-3-chloroacrylates
  作者：Xian Huang、Aiming Sun

  DOI：10.1021/jo0006977

  日期：2000.10.1

  Regio- and stereoselectivity in the chloropalladation carbonylation reaction of different acetylenic selenides in the presence of 0.05 equiv of PdCl2 and 3 equiv of cupric chloride under 1 atm of carbon monoxide affording 2-seleno-3-chloroacrylates were investigated. Opposite stereoselectivities were observed with 2-phenylethynyl selenides and 8-alkylethynyl selenides the reactions of 2-phenylethynyl selenides afforded (E)-2-seleno-3-chloro-3-phenylacrylates, while the reactions of 8-alkyl-ethynyl selenides gave (Z)-2-seleno-3-chloro-3-alkylacrylates. A chloropalladation carbonylation mechanism for this reaction was proposed. The regio- and stereoselective chloropalladation of the carbon-carbon triple bond in acetylenic selenides affords 1-enylpalladium intermediates, in which : the palladium atom connects with the carbon atom bonding with the selenium atom. Carbonylation in the presence of an alcohol affords 2-seleno-3-chloroacrylates.