(2S,3R,4S,5S)-3,4-O-isopropylidene-5-methyl-2-((naphthalen-2-yl)methyl)tetrahydrofuran-3,4-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3R,4S,5S)-3,4-O-isopropylidene-5-methyl-2-((naphthalen-2-yl)methyl)tetrahydrofuran-3,4-diol
• 英文别名: (3aR,4S,6S,6aS)-2,2,6-trimethyl-4-(naphthalen-2-ylmethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: SXZZSKXCGGQXCE-GYIHYUDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S,4R)-3,4-O-isopropylidene-hex-5-ene-2,3,4-triol 、 2-溴萘 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 3.0h， 以15%的产率得到(E)-(3S,4R)-3,4-O-isopropylidene-6-(naphthalen-2-yl)hex-5-ene-2,3,4-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

文献信息

• Domino reaction: Pd(II)-catalyzed cyclization of unsaturated polyols and cross-coupling
  作者：Angelika Lásiková、Jana Doháňošová、Lucia Hlavínová、Martial Toffano、Giang Vo-Thanh、Jozef Kožíšek、Tibor Gracza

  DOI：10.1016/j.tetasy.2012.05.020

  日期：2012.6

  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.