(E)-2-formylphenyl 2-(4-chlorophenyl)ethenesulfonate | 1339031-06-9

• 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: (E)-2-formylphenyl 2-(4-chlorophenyl)ethenesulfonate
• CAS: 1339031-06-9
• 化学式: C₁₅H₁₁ClO₄S
• 分子量: 322.769
• InChiKey: TZXHJTJCFIGDHD-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (E)-2-formylphenyl 2-(4-chlorophenyl)ethenesulfonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 22.0h， 以60%的产率得到3-[(4-chlorophenyl)methoxymethyl]benzo[e][1,2]oxathiine-2,2-dioxide
  参考文献：
  名称：

  Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences

  摘要：

  We have developed a solvent-dependent method for the synthesis of novel benzo-delta-sultone scaffolds. A variety of benzylbenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxides were obtained in high yields in DMF using a one-pot, DBU-catalyzed condensation of 2-hydroxybenzaldehydes with a number of (E)-2-phenylethenesulfonyl chlorides. On the other hand, the initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonate derivatives underwent DBU-catalyzed reactions to a series of 3-[methoxy(phenyl)methyl]benzo[e][1,2]oxathiine-2,2-dioxides in moderate to good yields in MeOH. These reactions presumably proceed via DBU-catalyzed O-sulfonylation/intramolecular Baylis-Hillman/1,3-H shift or dehydration tandem sequences, respectively.

  DOI：

  10.1021/jo201506d
• 作为产物：
  描述：

  水杨醛 、 (E)-2-(4-氯苯基)乙烯磺酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以95%的产率得到(E)-2-formylphenyl 2-(4-chlorophenyl)ethenesulfonate
  参考文献：
  名称：

  Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences

  摘要：

  We have developed a solvent-dependent method for the synthesis of novel benzo-delta-sultone scaffolds. A variety of benzylbenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxides were obtained in high yields in DMF using a one-pot, DBU-catalyzed condensation of 2-hydroxybenzaldehydes with a number of (E)-2-phenylethenesulfonyl chlorides. On the other hand, the initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonate derivatives underwent DBU-catalyzed reactions to a series of 3-[methoxy(phenyl)methyl]benzo[e][1,2]oxathiine-2,2-dioxides in moderate to good yields in MeOH. These reactions presumably proceed via DBU-catalyzed O-sulfonylation/intramolecular Baylis-Hillman/1,3-H shift or dehydration tandem sequences, respectively.

  DOI：

  10.1021/jo201506d

文献信息

• Efficient access to novel hexahydro-chromene and tetrahydro-pyrano[2,3-d]pyrimidine-annulated benzo-δ-sultones via a domino Knöevenagel-hetero-Diels–Alder reaction in water
  作者：Mehdi Ghandi、Elham Mohammadimehr、Masoud Sadeghzadeh、Abolfazl Hasani Bozcheloei

  DOI：10.1016/j.tet.2011.09.010

  日期：2011.11

  An efficient catalyst-free, diastereosective synthesis of novel hexahydro-chromene and tetrahydro-pyrano[2,3-d]pyrimidine-annulated benzo-delta-sultones is described. A number of 2-formyl-4-phenyl (E)-2-phenylethenesulfonates were synthesized and underwent a one-pot domino Knoevenagel-hetero-Diels-s-Alder reaction, respectively, with dimedone and N,N-dimethylbarbituric acid in water, affording the desired products in moderate to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences
  作者：Mehdi Ghandi、Abolfazl Hasani Bozcheloei、Seyed Hadi Nazari、Masoud Sadeghzadeh

  DOI：10.1021/jo201506d

  日期：2011.12.16

  We have developed a solvent-dependent method for the synthesis of novel benzo-delta-sultone scaffolds. A variety of benzylbenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxides were obtained in high yields in DMF using a one-pot, DBU-catalyzed condensation of 2-hydroxybenzaldehydes with a number of (E)-2-phenylethenesulfonyl chlorides. On the other hand, the initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonate derivatives underwent DBU-catalyzed reactions to a series of 3-[methoxy(phenyl)methyl]benzo[e][1,2]oxathiine-2,2-dioxides in moderate to good yields in MeOH. These reactions presumably proceed via DBU-catalyzed O-sulfonylation/intramolecular Baylis-Hillman/1,3-H shift or dehydration tandem sequences, respectively.