6-Benzenesulfonyl-nona-6,7-dien-1-ol | 372492-39-2

• 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: 6-Benzenesulfonyl-nona-6,7-dien-1-ol
• CAS: 372492-39-2
• 化学式: C₁₅H₂₀O₃S
• 分子量: 280.388
• InChiKey: KAGHNWDBAABDGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Benzenesulfonyl-nona-6,7-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93%的产率得到6-(phenylsulfonyl)nona-6,7-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
• 作为产物：
  描述：

  8-(tert-butyldimethylsilyloxy)oct-3-yn-2-ol 在 4-甲基苯磺酸吡啶 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 6-Benzenesulfonyl-nona-6,7-dien-1-ol
  参考文献：
  名称：

  A New Entry to Oxacycles via Base-Catalyzed Endo Mode Cyclization of Allenyl Sulfoxides and Sulfones

  摘要：

  [GRAPHICS]Treatment of the allenyl sulfoxides and sulfones possessing a proper delta -hydroxy appendage at the C-1 position with potassium tert-butoxide effected endo mode ring closure at the sp-hybridized carbon center of the allenyl moiety to provide the five- to eight-membered oxacycles in high yields.

  DOI：

  10.1021/ol0101842

文献信息

• Miyakoshi, Naoki; Ohgaki, Yuki; Masui, Kosuke, Heterocycles, 2007, vol. 74, # C, p. 185 - 189
  作者：Miyakoshi, Naoki、Ohgaki, Yuki、Masui, Kosuke、Mukai, Chisato

  DOI：——

  日期：——
• A New Entry to Oxacycles via Base-Catalyzed Endo Mode Cyclization of Allenyl Sulfoxides and Sulfones
  作者：Chisato Mukai、Haruhisa Yamashita、Miyoji Hanaoka

  DOI：10.1021/ol0101842

  日期：2001.10.1

  [GRAPHICS]Treatment of the allenyl sulfoxides and sulfones possessing a proper delta -hydroxy appendage at the C-1 position with potassium tert-butoxide effected endo mode ring closure at the sp-hybridized carbon center of the allenyl moiety to provide the five- to eight-membered oxacycles in high yields.
• 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.