(+/-)-trans-3-(tert-butyldimethylsilyloxy)-2-(naphthalen-2-ylmethyl)tetrahydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-trans-3-(tert-butyldimethylsilyloxy)-2-(naphthalen-2-ylmethyl)tetrahydrofuran
• 英文别名: tert-butyl-dimethyl-[(2S,3R)-2-(naphthalen-2-ylmethyl)oxolan-3-yl]oxysilane
• 化学式: C₂₁H₃₀O₂Si
• 分子量: 342.554
• InChiKey: HJCDWDVSJMMKGS-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴萘 、 3-(tert-butyldimethylsilyloxy)pent-4-en-1-ol 在 1,4-双(二苯基膦)丁烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (+/-)-cis-3-(tertbutyldimethylsilyloxy)-2-(naphthalen-2-ylmethyl)tetrahydrofuran 、 (+/-)-trans-3-(tert-butyldimethylsilyloxy)-2-(naphthalen-2-ylmethyl)tetrahydrofuran
  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.