4-(phenylsulfonyl)hexa-4,5-dien-1-al | 1231155-14-8

• 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: 4-(phenylsulfonyl)hexa-4,5-dien-1-al
• CAS: 1231155-14-8
• 化学式: C₁₂H₁₂O₃S
• 分子量: 236.291
• InChiKey: ZYWUSOPAPOXHME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  4-(phenylsulfonyl)hexa-4,5-dien-1-al 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以23%的产率得到2-methyl-3-(phenylsulfonyl)-4H-pyran
  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：

  4-(phenylsulfonyl)hexa-4,5-dien-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以100%的产率得到4-(phenylsulfonyl)hexa-4,5-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

• Regioselective Intramolecular [3+2] Annulation of Allene-Nitrones
  作者：Fuyuhiko Inagaki、Harumi Kobayashi、Chisato Mukai

  DOI：10.1248/cpb.60.381

  日期：——

  The regioselective intramolecular 1,3-dipolar cycloaddition of the phenylsulfonylallene-nitrone derivatives has been developed. This reaction showed that the distal double bond of the allene exclusively reacted with the nitrone group to produce the bicyclic isoxazolidine derivatives regardless of the substitution pattern on the allenyl moiety.

  已经开发了苯基磺酰基烯丙基-亚硝基衍生物的区域选择性分子内的1，3-偶极环加成。该反应表明，无论烯丙基部分上的取代方式如何，丙二烯的远端双键仅与硝酮基反应生成双环异恶唑烷衍生物。
• 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.