E-3-methyl-3-hydroxy-1-phenylsulfonylbut-1-ene | 129355-52-8

• 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: E-3-methyl-3-hydroxy-1-phenylsulfonylbut-1-ene
• 英文别名: (E)-4-(benzenesulfonyl)-2-methylbut-3-en-2-ol
• CAS: 129355-52-8
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: SMCUNTCJOFRJQP-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  E-3-methyl-3-hydroxy-1-phenylsulfonylbut-1-ene 在 丙酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 36.0h， 生成 ethyl (E)-5-methyl-2,4-hexadienoate
  参考文献：
  名称：

  γ-羟基乙烯基砜通过乙烯酮缩醛衍生物的克莱森重排。功能化（2E，4E）-链二烯酸酯的新进入

  摘要：

  原位制备的γ-羟基乙烯基砜的乙烯酮缩醛进行克莱森重排，得到3-苯基磺酰基酯。通过碱辅助消除苯亚磺酸将这些化合物转化为（2E，4E）-二烯二酸酯。

  DOI：

  10.1016/s0040-4039(98)01151-4
• 作为产物：
  描述：

  3-methyl-1-(phenylsulfonyl)but-2-ene 生成 E-3-methyl-3-hydroxy-1-phenylsulfonylbut-1-ene
  参考文献：
  名称：

  环戊二烯基（膦）-（α-苯磺酰基烷基）镍配合物的反应；由砜形成醛和烯烃

  摘要：

  已经研究了环戊二烯基（膦）（α-苯磺酰基烷基）镍配合物的三个反应：（i）显示用氧氧化提供了一种由砜制备醛的新的有效方法；（ii）用强路易斯酸处理得到相应的末端烯烃（机理进行了简要讨论）；（iii）通过强碱去质子化得到阴离子物质，其可以被碘甲烷烷基化。

  DOI：

  10.1016/0022-328x(90)87184-f

文献信息

• Efficient conversion of olefins into epoxides, bromohydrins, and dibromides with sodium bromide in water-organic solvent electrolysis systems
  作者：Sigeru Torii、Kenji Uneyama、Hideo Tanaka、Tooru Yamanaka、Tsuneo Yasuda、Michio Ono、Yumiko Kohmoto

  DOI：10.1021/jo00329a032

  日期：1981.7
• Facile synthesis of E-γ-hydroxy-α,β-unsaturated sulfones from aldehydes
  作者：Esteban Dominguez、Juan Carlos Carretero

  DOI：10.1016/s0040-4039(00)97396-9

  日期：1990.1
• A practical route to (E)-γ-hydroxy-αβ-unsaturated phenyl sulfones
  作者：Esteban Dominguez、Juan Carlos Carretero

  DOI：10.1016/s0040-4020(01)87900-x

  日期：1990.1
• A convenient synthesis of .gamma.-hydroxy .alpha.,.beta.-unsaturated sulfones
  作者：Barry M. Trost、Timothy A. Grese

  DOI：10.1021/jo00009a050

  日期：1991.4
• Intramolecular palladium-catalyzed cycloadditions with a cleavable tether
  作者：Barry M. Trost、Timothy A. Grese

  DOI：10.1021/ja00019a037

  日期：1991.9

  A facile synthesis of 2-(acyloxy)-3-methylene-4-(trimethylsilyl)butyric acids evolves from the use of tris(phenylthio)acetaldehyde as a practical glyoxylic ester equivalent. Introduction of the bifunctional donor of a [3 + 2] cycloaddition proceeds simply by esterification of an alcohol possessing TMM-PdL2 acceptor units. The synthetic flexibility of the sulfone leads to the choice of alpha, beta-unsaturated sulfones as the acceptors. Palladium-catalyzed cycloadditions proceed smoothly at temperatures as low as room temperature. Depending upon the substitution pattern and especially the conformation of the substrate, tethering the ester containing the bifunctional TMM unit at the carbon allylic to the acceptor provides substrates that predominantly to exclusively undergo cycloaddition rather than processes dominated by an alternative Pd(0)-catalyzed ionization. Since the ester linkage is easily cleaved, this sequence serves as a convenient strategy for controlled TMM-PdL2 cycloadditions. For example, the diastereofacial selectivity of this intramolecular process involves attack syn to the allylic oxygen in a six- or seven-membered-ring acceptor but anti to this oxygen in an intermolecular process. A diastereocontrolled cyclopentenone annulation is developed. Interestingly, the intramolecular cycloaddition of eight- and twelve-membered rings proceeds anti to the allylic oxygen. As an aside, the indefinite shelf life of the crystalline tris(phenylthio)acetaldehyde makes it a convenient glyoxylate synthon.