(4'S,5'S)-5-(5-Ethyl-2,2-dimethyldioxolan-4-yl)pentan-2-one | 110659-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4'S,5'S)-5-(5-Ethyl-2,2-dimethyldioxolan-4-yl)pentan-2-one
• 英文别名: 4-ethyl-2,2-dimethyl-5-(4-oxopentyl)-1,3-dioxolane
• CAS: 110659-30-8
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: SITAIWKKYVKIJD-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4'S,5'S)-5-(5-Ethyl-2,2-dimethyldioxolan-4-yl)pentan-2-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,7S)-exo-brevicomin
  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)-(-)-(1-Iodo-2-hydroxyethyl)-2,5-dihydrofuran 在 palladium on activated charcoal 氢氧化钾 、 三甲基氯硅烷 、 无水碳酸镉 、 氢气 、 sodium iodide 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， -70.0~25.0 ℃ 、151.99 kPa 条件下， 反应 14.0h， 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

文献信息

• Synthesis of both the enantiomers of 7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]oct-3-ene, the (house mouse) pheromone
  作者：Kenji Mori、Young-Bae Seu

  DOI：10.1016/s0040-4020(01)96072-7

  日期：1986.1

  Both the enantiomers of the pheromone of the male mouse Musmusculus, exo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]oct-3-ene, were synthesized from the enantiomers of tartaric acid.

  雄性小鼠Musmusculus信息素的两个对映异构体exo-7-乙基-5-甲基-6,8-二氧杂双环[3.2.1] oct-3-ene均由酒石酸的对映异构体合成。