(E)-(2S,3R)-2,3-O-isopropylidene-5-(naphthalen-2-yl)pent-4-ene-1,2,3-triol | 1393803-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-(2S,3R)-2,3-O-isopropylidene-5-(naphthalen-2-yl)pent-4-ene-1,2,3-triol
• CAS: 1393803-99-0
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: HMGWXXDVLGSFMT-CSTAJBCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-溴萘 、 (4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane 在 双(2-二苯基磷苯基)醚 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以15%的产率得到(E)-(2S,3R)-2,3-O-isopropylidene-5-(naphthalen-2-yl)pent-4-ene-1,2,3-triol
  参考文献：
  名称：

  Domino reaction: Pd(II)-catalyzed cyclization of unsaturated polyols and cross-coupling

  摘要：

  The Pd-catalyzed cyclization and cross-coupling of hydroxylated alkenes in domino reactions are described. The alkenols undergo Pd-catalyzed cyclization and subsequent cross-coupling reactions with aryl bromides to afford (poly)hydroxylated tetrahydrofuran derivatives. The relationship between the stereoselectivity of the transformation and the steric and/or electronic effects of the substrates has also been studied. The diastereoselectivity of the cyclization of gamma-hydroxyalkenes 1.4-6 is influenced by the allylic hydroxyl functionality in favor of 2,3-cis stereoselectivity. Substitution at the C-1 carbon in alkenitols 7 and 8 ensured the formation of products with 2,5-trans diastereoselectivity (up to >19:1), independent of additional substituents. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.020