2-formyl-6-methoxyphenyl (E)-2-phenylethenesulfonate | 1339031-04-7

• 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: 2-formyl-6-methoxyphenyl (E)-2-phenylethenesulfonate
• 英文别名: (2-formyl-6-methoxyphenyl) (E)-2-phenylethenesulfonate
• CAS: 1339031-04-7
• 化学式: C₁₆H₁₄O₅S
• 分子量: 318.35
• InChiKey: DNNUNXVTFULOKA-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 2-formyl-6-methoxyphenyl (E)-2-phenylethenesulfonate 以 甲苯 为溶剂， 反应 3.0h， 以87%的产率得到6-methoxy-1-methyl-3-phenyl-1,2,3,3a,4,9b-hexahydrobenzo[5,6][1,2]oxathiino[4,3-b]pyrrole 4,4-dioxide
  参考文献：
  名称：

  分子内1,3-偶极环加成反应合成新型三环和四环磺内酯骨架

  摘要：

  由（E）-2-苯基乙烯磺酰氯与2-羟基苯甲醛衍生物的缩合反应制得的2-甲酰基苯基-（E）-2-苯基乙烯磺酸酯与甲基或苯基羟胺，肌氨酸和1-脯氨酸进行分子内[3 + 2]环加成反应，分别以良好的收率得到相应的新型异恶唑烷，吡咯烷和吡咯嗪环化的γ，δ-苯并-δ-磺内酯。通过单晶X射线衍射进行分子结构的明确分配。

  DOI：

  10.1016/j.tet.2012.02.053
• 作为产物：
  描述：

  2-羟基-6-甲氧基苯甲醛 、 反-β-苯乙烯磺酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以95%的产率得到2-formyl-6-methoxyphenyl (E)-2-phenylethenesulfonate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.09.010

文献信息

• Synthesis of novel pentacyclic thiopyrano indole-annulated benzo-δ-sultone derivatives via a domino Knoevenagel-hetero-Diels–Alder reaction in water
  作者：Firouz Matloubi Moghaddam、Mohammad Reza Khodabakhshi、Mostafa Kiamehr、Zahra Ghahremannejad

  DOI：10.1016/j.tetlet.2013.03.070

  日期：2013.5

  An efficient synthesis of novel pentacyclic thiopyrano indole-annulated benzo-δ-sultone derivatives is achieved via intramolecular domino Knoevenagel-hetero-Diels–Alder reaction of 2-formylphenyl (E)-2-phenylethenyl sulfonates and indoline-2-thiones in aqueous medium. The products are formed in good yields with high regio- and stereoselectivity.

  通过分子内的多米诺骨牌Knoevenagel-杂-Diels-Alder反应，在水性介质中2-甲酰基苯基（E）-2-苯基乙烯基磺酸盐和二氢吲哚-2-硫酮，可以有效合成新型的五环噻喃并吲哚环化的苯并-δ-磺内酯衍生物。以高产率和高区域选择性和立体选择性形成产物。
• 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.
• Synthesis of novel tricyclic and tetracyclic sultone scaffolds via intramolecular 1,3-dipolar cycloaddition reactions
  作者：Mehdi Ghandi、Abuzar Taheri、Abolfazl Hasani Bozcheloei、Alireza Abbasi、Reza Kia

  DOI：10.1016/j.tet.2012.02.053

  日期：2012.5

  The initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonates from the condensation of (E)-2-phenylethenesulfonyl chloride with 2-hydroxybenzaldehyde derivatives underwent intramolecular [3+2] cycloaddition with methyl or phenylhydroxylamine, sarcosine, and l-proline, affording the corresponding novel isoxazolidine, pyrrolidine and pyrrolizidine-annulated γ,δ-benzo-δ-sultones, respectively, in

  由（E）-2-苯基乙烯磺酰氯与2-羟基苯甲醛衍生物的缩合反应制得的2-甲酰基苯基-（E）-2-苯基乙烯磺酸酯与甲基或苯基羟胺，肌氨酸和1-脯氨酸进行分子内[3 + 2]环加成反应，分别以良好的收率得到相应的新型异恶唑烷，吡咯烷和吡咯嗪环化的γ，δ-苯并-δ-磺内酯。通过单晶X射线衍射进行分子结构的明确分配。
• 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.