4-(phenylsulfonyl)but-2-en-1-ol | 213909-30-9

• 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)but-2-en-1-ol
• 英文别名: (Z)-4-(benzenesulfonyl)but-2-en-1-ol
• CAS: 213909-30-9
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: ZMRIPMQPSGWABC-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  4-(phenylsulfonyl)but-2-en-1-ol 在 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 反应 2.0h， 生成 (Z)-(4S,5R)-5-Amino-4-benzenesulfonyl-5-(4-methoxy-phenyl)-pent-2-en-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of functionalized piperidine derivatives: synthesis of (S)-anatabine

  摘要：

  A short and efficient chiral synthesis of 6-aryl-5-phenylsulfonyl-1,2,5,6-tetrahydropyridines was achieved in moderate yield and with good selectivity. The absolute configurations were assigned by extending the methodology to (S)-anatabine and as well with NMR experiments. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00225-0
• 作为产物：
  描述：

  (Z)-4-chloro-but-2-en-1-ol 、 sodium benzenesulfonate 以 甲醇 为溶剂， 反应 8.0h， 以60%的产率得到4-(phenylsulfonyl)but-2-en-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of functionalized piperidine derivatives: synthesis of (S)-anatabine

  摘要：

  A short and efficient chiral synthesis of 6-aryl-5-phenylsulfonyl-1,2,5,6-tetrahydropyridines was achieved in moderate yield and with good selectivity. The absolute configurations were assigned by extending the methodology to (S)-anatabine and as well with NMR experiments. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00225-0

文献信息

• Hydrosulfonylation of Unactivated Alkenes by Visible Light Photoredox Catalysis
  作者：Juan-Juan Wang、Wei Yu

  DOI：10.1021/acs.orglett.9b03636

  日期：2019.11.15

  hydrosulfonylation of unactivated alkenes with sodium sulfinates was realized via [Ir(dF(CF3)ppy)2(dtbbpy)]PF6-mediated visible light photoredox catalysis. The presence of an acid such as acetic acid is essential for the reaction to take place. A variety of unactivated alkenes can be transformed into sulfones with good yield and high regioselectivity using this reaction, which is proposed to proceed by a radical

  通过[Ir（dF（CF3）ppy）2（dtbbpy）] PF6介导的可见光光氧化还原催化作用，实现了未活化烯烃与亚磺酸钠的抗马氏复合羰基化反应。酸例如乙酸的存在对于反应的发生是必不可少的。使用该反应，可以将多种未活化的烯烃以良好的产率和高的区域选择性转化为砜，这被认为是通过自由基机理进行的。
• 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.