(E)-1-(phenylsulfonyl)-1-buten-4-ol | 135619-57-7

• 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)-1-(phenylsulfonyl)-1-buten-4-ol
• 英文别名: (E)-4-(phenylsulfonyl)but-3-en-1-ol；(E)-4-(benzenesulfonyl)but-3-en-1-ol
• CAS: 135619-57-7
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: UNHWWNVWIPGRPD-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：

  (E)-1-(phenylsulfonyl)-1-buten-4-ol 在 CH₃O₃S*C₅H₅N 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.0h， 以64%的产率得到(E)-4-(phenylsulfonyl)but-3-enal
  参考文献：
  名称：

  Organocatalyst-mediated enantioselective intramolecular Michael addition of aldehydes to vinyl sulfones

  摘要：

  Chiral amines with a hydrogen bond donor promote the intramolecular conjugate addition of aldehydes to vinyl sulfones. Chiral cyclic sulfone-aldehydes are obtained in good yields with an ee of up to 82%. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.043
• 作为产物：
  描述：

  γ-丁内酯 、 苯砜基甲基膦酸二乙酯 在 二异丁基氢化铝 、 sodium hydride 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 3.0h， 以51%的产率得到(E)-1-(phenylsulfonyl)-1-buten-4-ol
  参考文献：
  名称：

  Organocatalyst-mediated enantioselective intramolecular Michael addition of aldehydes to vinyl sulfones

  摘要：

  Chiral amines with a hydrogen bond donor promote the intramolecular conjugate addition of aldehydes to vinyl sulfones. Chiral cyclic sulfone-aldehydes are obtained in good yields with an ee of up to 82%. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.043

文献信息

• 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.
• US4168379A
  申请人：——

  公开号：US4168379A

  公开（公告）日：1979-09-18
• Organocatalyst-mediated enantioselective intramolecular Michael addition of aldehydes to vinyl sulfones
  作者：Chloée Bournaud、Estelle Marchal、Adrien Quintard、Sarah Sulzer-Mossé、Alexandre Alexakis

  DOI：10.1016/j.tetasy.2010.03.043

  日期：2010.7

  Chiral amines with a hydrogen bond donor promote the intramolecular conjugate addition of aldehydes to vinyl sulfones. Chiral cyclic sulfone-aldehydes are obtained in good yields with an ee of up to 82%. (C) 2010 Elsevier Ltd. All rights reserved.