3-(phenylsulfonyl)penta-3,4-dien-1-al | 1231154-88-3

• 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: 3-(phenylsulfonyl)penta-3,4-dien-1-al
• CAS: 1231154-88-3
• 化学式: C₁₁H₁₀O₃S
• 分子量: 222.265
• InChiKey: OTGXYRLTMKTZMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(phenylsulfonyl)penta-3,4-dien-1-al 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以19%的产率得到(2-Methyl-3-furyl)-phenyl-sulfon
  参考文献：
  名称：

  Chemistry of allenic/propargylic anions generated by base treatment of sulfonylallenes: synthesis of 1-alkynyl-1-sulfonylcycloalkanes and cycloalkanols

  摘要：

  The intramolecular trapping of allenyl/propargyl anions, generated from sulfonylallenes with the proper base, by a haloalkyl group or an aldehyde functionality was investigated. The treatment of 1-(omega-iodoalkyl)-1-(phenylsulfonyl)allenes with TBAF or NaH in DMF efficiently produced the 1-alkynyl-1-(phenylsulfonyl)-substituted three- to seven-membered carbocycles. The allenyl/propargyl anions could also be intramolecularly trapped using a terminal aldehyde to stereoselectively afford the 2-alkynyl-2-(phenylsulfonyl)-substituted five- and six-membered cycloalkanols. The latter reaction could be performed using a catalytic amount of TBAF or DBU. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.071
• 作为产物：
  描述：

  3-(phenylsulfonyl)penta-3,4-dien-1-ol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 以86%的产率得到3-(phenylsulfonyl)penta-3,4-dien-1-al
  参考文献：
  名称：

  Chemistry of allenic/propargylic anions generated by base treatment of sulfonylallenes: synthesis of 1-alkynyl-1-sulfonylcycloalkanes and cycloalkanols

  摘要：

  The intramolecular trapping of allenyl/propargyl anions, generated from sulfonylallenes with the proper base, by a haloalkyl group or an aldehyde functionality was investigated. The treatment of 1-(omega-iodoalkyl)-1-(phenylsulfonyl)allenes with TBAF or NaH in DMF efficiently produced the 1-alkynyl-1-(phenylsulfonyl)-substituted three- to seven-membered carbocycles. The allenyl/propargyl anions could also be intramolecularly trapped using a terminal aldehyde to stereoselectively afford the 2-alkynyl-2-(phenylsulfonyl)-substituted five- and six-membered cycloalkanols. The latter reaction could be performed using a catalytic amount of TBAF or DBU. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.071

文献信息

• Chemistry of allenic/propargylic anions generated by base treatment of sulfonylallenes: synthesis of 1-alkynyl-1-sulfonylcycloalkanes and cycloalkanols
  作者：Shinji Kitagaki、Satoshi Teramoto、Yuu Ohta、Harumi Kobayashi、Mika Takabe、Chisato Mukai

  DOI：10.1016/j.tet.2010.03.071

  日期：2010.5

  The intramolecular trapping of allenyl/propargyl anions, generated from sulfonylallenes with the proper base, by a haloalkyl group or an aldehyde functionality was investigated. The treatment of 1-(omega-iodoalkyl)-1-(phenylsulfonyl)allenes with TBAF or NaH in DMF efficiently produced the 1-alkynyl-1-(phenylsulfonyl)-substituted three- to seven-membered carbocycles. The allenyl/propargyl anions could also be intramolecularly trapped using a terminal aldehyde to stereoselectively afford the 2-alkynyl-2-(phenylsulfonyl)-substituted five- and six-membered cycloalkanols. The latter reaction could be performed using a catalytic amount of TBAF or DBU. (C) 2010 Elsevier Ltd. All rights reserved.