1-phenyl-4-phenylsulfanyl-2-butyn-1-ol | 491877-80-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-phenyl-4-phenylsulfanyl-2-butyn-1-ol
• 英文别名: 4-phenyl-1-phenylthio-2-butyn-4-ol；1-phenyl-4-phenylsulfanyl-but-2-yn-1-ol；1-Phenyl-4-phenylsulfanylbut-2-yn-1-ol
• CAS: 491877-80-6
• 化学式: C₁₆H₁₄OS
• 分子量: 254.353
• InChiKey: IMPHOBPNMUCRGF-UHFFFAOYSA-N

物化性质

• 沸点：
  440.0±40.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-4-phenylsulfanyl-2-butyn-1-ol 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以87%的产率得到4-hydroxy-4-phenyl-1-phenylthio-1,2-butadiene
  参考文献：
  名称：

  Convenient method for the preparation of 1-phenylthio-3-alken-1-ynes and 4-hydroxy-1-phenylthio-1,2-alkadienes from a common precursor

  摘要：

  4-Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)- and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomers were formed in preference to the (E)-isomers. Further treatment of the mixture with a base converted the (Z)-isomers into (E)-isomers. On the other hand, the reaction of 5 with KHMDS gave the corresponding 4-hydroxy-1-phenythio-1,2-alkadienes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01380-1
• 作为产物：
  描述：

  thiophenolate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1-phenyl-4-phenylsulfanyl-2-butyn-1-ol
  参考文献：
  名称：

  Iron(II)-Catalyzed Sulfimidation and [2,3]-Sigmatropic Rearrangement of Propargyl Sulfides with tert-Butoxycarbonyl Azide. Access to N-Allenylsulfenimides

  摘要：

  The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN(3)) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl(2) as catalyst the reaction proceeds at 0 degreesC with a number of different propargyl sulfides in 31-73% isolated yield. The reaction is limited by product instability toward catalyst and termination of the catalytic cycle by excess BocN3. N-Allenylsulfenimide 2b smoothly undergoes catalytic hydrogenation and a Diels-Alder reaction with cyclopentadiene.

  DOI：

  10.1021/jo0340410

文献信息

• Electrophilic cyclization of 4-thio-but-2-yn-1-ols via 1,2-migration of the thio group: efficient synthesis of 2,4-dihalo-3-thio-substituted furans
  作者：Hongwei Zhou、Jinzhong Yao、Guoliang Liu

  DOI：10.1016/j.tetlet.2007.11.092

  日期：2008.1

  A facile and efficient method for the synthesis of 2,4-dihalo-3-thio-furans via the electrophilic cyclization and 1,2-migration of the thio group of 4-thio-but-2-yn-1-ols was developed. As a result of the ready availability of starting materials and the simple and convenient operation, this synthetic route would have potential utility in organic synthesis.

  开发了一种通过亲电子环化和4-硫代丁-2-yn-1-醇硫基的1,2-迁移来合成2,4-二卤-3-硫代呋喃的简便有效方法。由于起始材料的容易获得和简单方便的操作，这种合成路线将在有机合成中具有潜在的实用性。
• Reduction of propargylic sulfones to (Z)-allylic sulfones using zinc and ammonium chloride
  作者：Helen M. Sheldrake、Timothy W. Wallace

  DOI：10.1016/j.tetlet.2007.04.099

  日期：2007.6

  Propargylic sulfones can be cis-hydrogenated using commercial zinc powder and ammonium chloride in THF-water at room temperature, the major products being the corresponding (Z)-allylic sulfones. Other reducible groups (alkene, benzyloxy) are not affected. Allenylsulfones are implicated in one of the possible reaction pathways. (c) 2007 Elsevier Ltd. All rights reserved.
• DNA cleavage of novel propargylic sulfones. Enhancement of potency via intercalating interaction
  作者：Wei-Min Dai、Kin Chiu Fong、Hiroshi Danjo、Sei-ichi Nishimoto、Michael Solow、Wing Leung Mak、Mau Lam Yeung

  DOI：10.1016/0960-894x(96)00177-1

  日期：1996.5
• Iron(II)-Catalyzed Sulfimidation and [2,3]-Sigmatropic Rearrangement of Propargyl Sulfides with <i>tert</i>-Butoxycarbonyl Azide. Access to <i>N</i>-Allenylsulfenimides
  作者：James P. Bacci、Kevin L. Greenman、David L. Van Vranken

  DOI：10.1021/jo0340410

  日期：2003.6.1

  The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN(3)) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl(2) as catalyst the reaction proceeds at 0 degreesC with a number of different propargyl sulfides in 31-73% isolated yield. The reaction is limited by product instability toward catalyst and termination of the catalytic cycle by excess BocN3. N-Allenylsulfenimide 2b smoothly undergoes catalytic hydrogenation and a Diels-Alder reaction with cyclopentadiene.
• Convenient method for the preparation of 1-phenylthio-3-alken-1-ynes and 4-hydroxy-1-phenylthio-1,2-alkadienes from a common precursor
  作者：Atsushi Ogawa、Kazunari Sakagami、Akiko Shima、Hitoshi Suzuki、Satsuki Komiya、Yoshinori Katano、Oyo Mitsunobu

  DOI：10.1016/s0040-4039(02)01380-1

  日期：2002.9

  4-Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)- and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomers were formed in preference to the (E)-isomers. Further treatment of the mixture with a base converted the (Z)-isomers into (E)-isomers. On the other hand, the reaction of 5 with KHMDS gave the corresponding 4-hydroxy-1-phenythio-1,2-alkadienes. (C) 2002 Elsevier Science Ltd. All rights reserved.