(4S,5S)-(-)-4-Ethyl-2,2-dimethyl-5-<3-(2-methyl-1,3-dithian-2-yl)propyl>-1,3-dioxolane | 149818-51-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (4S,5S)-(-)-4-Ethyl-2,2-dimethyl-5-<3-(2-methyl-1,3-dithian-2-yl)propyl>-1,3-dioxolane
• CAS: 149818-51-9
• 化学式: C₁₅H₂₈O₂S₂
• 分子量: 304.518
• InChiKey: YHBKMKTYHRLTFO-STQMWFEESA-N

物化性质

• 沸点：
  385.1±32.0 °C(predicted)
• 密度：
  1.012±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-(-)-4-Ethyl-2,2-dimethyl-5-<3-(2-methyl-1,3-dithian-2-yl)propyl>-1,3-dioxolane 在 无水碳酸镉 、 mercury dichloride 作用下， 生成 (4'S,5'S)-5-(5-Ethyl-2,2-dimethyldioxolan-4-yl)pentan-2-one
  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
• 作为产物：
  描述：

  (2S,1'R)-(-)-2-<1-O-(p-Tolylsulfonyl)-2-O-pivaloylethyl>-2,5-dihydrofuran 在 palladium on activated charcoal 氢氧化钾 、 三甲基氯硅烷 、 氢气 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， -70.0~25.0 ℃ 、151.99 kPa 条件下， 反应 19.0h， 生成 (4S,5S)-(-)-4-Ethyl-2,2-dimethyl-5-<3-(2-methyl-1,3-dithian-2-yl)propyl>-1,3-dioxolane
  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