(S)-(+)-2-<2-O-(p-Tolylsulfonyl)ethyl>tetrahydrofuran | 149706-97-8

• 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: (S)-(+)-2-<2-O-(p-Tolylsulfonyl)ethyl>tetrahydrofuran
• 英文别名: (S)-(+)-2-[2-O-(p-Tolylsulfonyl)ethyl]tetrahydrofuran；2-[(2S)-oxolan-2-yl]ethyl 4-methylbenzenesulfonate
• CAS: 149706-97-8
• 化学式: C₁₃H₁₈O₄S
• 分子量: 270.35
• InChiKey: VUQWWGUPJYDAOH-LBPRGKRZSA-N

物化性质

• 沸点：
  408.9±18.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-<2-O-(p-Tolylsulfonyl)ethyl>tetrahydrofuran 在 三甲基氯硅烷 、 dilithium tetrachlorocuprate 、 对甲苯磺酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 (R)-(+)-1-(3-Iodopropyl)dodecyl acetate
  参考文献：
  名称：

  Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydrohexitols. 2. Synthesis of Acetal, Alcohol, Diol, Epoxide, Hydrocarbon, and Lactone Pheromones

  摘要：

  The potential of building blocks 1-3 for synthesis of enantiopure substances is illustrated by their transformation to various insect pheromones featuring functionalities specified in the title. A convenient synthesis of building block 3 from sorbitol is described.

  DOI：

  10.1021/jo00106a030
• 作为产物：
  描述：

  (2S)-(1-Iodo-2-hydroxyethyl)-2,5-dihydrofuran 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 7.0h， 生成 (S)-(+)-2-<2-O-(p-Tolylsulfonyl)ethyl>tetrahydrofuran
  参考文献：
  名称：

  Dihyro- and tetrahydrofuran building blocks from 1,4:3,6-dianhydromannitol. 1. Synthesis of (1S,5R,7R)-endo-(-)- and (1S,5R,7S)-(-)-exo-brevicomin and (R)-(+)-dodecanolide

  摘要：

  The eliminative ring fission of iodides derived from 1,4:3,6-dianhydromannitol3 has been exploited for preparing three enantiomerically pure species, 1-3, which feature a di-or tetrahydrofuran moiety and one or two stereogenic centers. These species are extremely versatile building blocks for the construction of natural products. Their potential was demonstrated by the synthesis of the title insect pheromones.

  DOI：

  10.1021/jo00069a015

文献信息

• Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydrohexitols. 2. Synthesis of Acetal, Alcohol, Diol, Epoxide, Hydrocarbon, and Lactone Pheromones
  作者：Claudio Paolucci、Claudio Mazzini、Antonino Fava

  DOI：10.1021/jo00106a030

  日期：1995.1

  The potential of building blocks 1-3 for synthesis of enantiopure substances is illustrated by their transformation to various insect pheromones featuring functionalities specified in the title. A convenient synthesis of building block 3 from sorbitol is described.
• Dihyro- and tetrahydrofuran building blocks from 1,4:3,6-dianhydromannitol. 1. Synthesis of (1S,5R,7R)-endo-(-)- and (1S,5R,7S)-(-)-exo-brevicomin and (R)-(+)-dodecanolide
  作者：Vanda Cere、Claudio Mazzini、Claudio Paolucci、Salvatore Pollicino、Antonino Fava

  DOI：10.1021/jo00069a015

  日期：1993.8

  The eliminative ring fission of iodides derived from 1,4:3,6-dianhydromannitol3 has been exploited for preparing three enantiomerically pure species, 1-3, which feature a di-or tetrahydrofuran moiety and one or two stereogenic centers. These species are extremely versatile building blocks for the construction of natural products. Their potential was demonstrated by the synthesis of the title insect pheromones.