3-(Benzenesulfonyl)oct-1-en-7-yn-2-yloxybenzene | 133931-62-1

• 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: 3-(Benzenesulfonyl)oct-1-en-7-yn-2-yloxybenzene
• 英文别名: 3-(benzenesulfonyl)oct-1-en-7-yn-2-yloxybenzene
• CAS: 133931-62-1
• 化学式: C₂₀H₂₀O₃S
• 分子量: 340.443
• InChiKey: VKCNYSXKRGAGHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(Benzenesulfonyl)oct-1-en-7-yn-2-yloxybenzene 在 sodium benzenesulfonate 、 溶剂黄146 作用下， 反应 16.0h， 生成 2-<(phenylsulfonyl)methyl>-1-cyclopentenyl methyl ketone
  参考文献：
  名称：

  Alkylation of 2-oxy-substituted 1-sulfonylallyl and 1-sulfonylvinyl anions. New routes to functionalized carbocycles and dihydrofurans

  摘要：

  Alkylation of the anion derived from 2-phenoxy-3-(phenylsulfonyl)-1-propene proceeds alpha to the phenylsulfonyl group and affords cyclic products from 1,omega-dihalides. Reaction of the monoalkylated products, in which a suitably positioned olefinic or acetylenic unit is present, with sodium benzenesulfinate-acetic acid gives functionalized acetylcyclopentenes and cyclohexenes via C-C bond formation from the allyl cation-sulfinate ion pair. In the vinyl sulfone series, deprotonation of (E)- or (Z)-2-alkoxyvinyl phenyl sulfones rapidly affords the more stable (E)-lithio derivative, an acetaldehyde anion equivalent which reacts normally with aldehydes, ketones, alkyl halides, and epoxides. The latter process may be effected in an intramolecular fashion. Thus, (E)-(2-phenylsulfonyl) vinyl ethers of 2,3-epoxy alcohols cyclize on treatment with amide bases to afford dihydrofurans whose stereochemistry is fully defined by that of the starting epoxy alcohol.

  DOI：

  10.1021/jo00011a021
• 作为产物：
  描述：

  苯酚 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.17h， 生成 3-(Benzenesulfonyl)oct-1-en-7-yn-2-yloxybenzene
  参考文献：
  名称：

  Alkylation of 2-oxy-substituted 1-sulfonylallyl and 1-sulfonylvinyl anions. New routes to functionalized carbocycles and dihydrofurans

  摘要：

  Alkylation of the anion derived from 2-phenoxy-3-(phenylsulfonyl)-1-propene proceeds alpha to the phenylsulfonyl group and affords cyclic products from 1,omega-dihalides. Reaction of the monoalkylated products, in which a suitably positioned olefinic or acetylenic unit is present, with sodium benzenesulfinate-acetic acid gives functionalized acetylcyclopentenes and cyclohexenes via C-C bond formation from the allyl cation-sulfinate ion pair. In the vinyl sulfone series, deprotonation of (E)- or (Z)-2-alkoxyvinyl phenyl sulfones rapidly affords the more stable (E)-lithio derivative, an acetaldehyde anion equivalent which reacts normally with aldehydes, ketones, alkyl halides, and epoxides. The latter process may be effected in an intramolecular fashion. Thus, (E)-(2-phenylsulfonyl) vinyl ethers of 2,3-epoxy alcohols cyclize on treatment with amide bases to afford dihydrofurans whose stereochemistry is fully defined by that of the starting epoxy alcohol.

  DOI：

  10.1021/jo00011a021

文献信息

• Alkylation of 2-oxy-substituted 1-sulfonylallyl and 1-sulfonylvinyl anions. New routes to functionalized carbocycles and dihydrofurans
  作者：Albert Padwa、William H. Bullock、Andrew D. Dyszlewski、S. W. McCombie、B. B. Shankar、A. K. Ganguly

  DOI：10.1021/jo00011a021

  日期：1991.5

  Alkylation of the anion derived from 2-phenoxy-3-(phenylsulfonyl)-1-propene proceeds alpha to the phenylsulfonyl group and affords cyclic products from 1,omega-dihalides. Reaction of the monoalkylated products, in which a suitably positioned olefinic or acetylenic unit is present, with sodium benzenesulfinate-acetic acid gives functionalized acetylcyclopentenes and cyclohexenes via C-C bond formation from the allyl cation-sulfinate ion pair. In the vinyl sulfone series, deprotonation of (E)- or (Z)-2-alkoxyvinyl phenyl sulfones rapidly affords the more stable (E)-lithio derivative, an acetaldehyde anion equivalent which reacts normally with aldehydes, ketones, alkyl halides, and epoxides. The latter process may be effected in an intramolecular fashion. Thus, (E)-(2-phenylsulfonyl) vinyl ethers of 2,3-epoxy alcohols cyclize on treatment with amide bases to afford dihydrofurans whose stereochemistry is fully defined by that of the starting epoxy alcohol.