1-(2-furyl)oct-2-yn-1-ol | 146133-42-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(2-furyl)oct-2-yn-1-ol
• 英文别名: 1-[2]Furyl-oct-2-in-1-ol；1-(Furan-2-yl)oct-2-yn-1-ol
• CAS: 146133-42-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: GPETUYICRKEGQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-furyl)oct-2-yn-1-ol 在 tris(dibenzylideneacetone)dipalladium (0) 吡啶 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (3Z)-2-(2-furyl)-3-hexylidene-2,3-dihydro-1,4-benzodioxin
  参考文献：
  名称：

  Asymmetric palladium-catalyzed annulation of benzene-1,2-diol and racemic secondary propargylic carbonates bearing two different substituents

  摘要：

  The palladium-catalyzed cyclization of benzene-1,2-diol with various racemic secondary propargyl carbonates having no acetylenic hydrogen in the presence of (R)-Binap as the chiral ligand afforded the two regioisomers of the corresponding 2,3-dihydro-1,4-dioxin derivatives in quite good yields, and also in enantioselectivities going from 40 to 97%. The cyclization of benzene-1,2-diol with methyl (R)-1-methyl-3-phenylpro-2-yn-1-yl carbonate in the presence of dppb as the achiral ligand afforded 2-benzylidene-3-methyl-2,3-dihydro-1,4-benzodioxine as the major product with 15% ee. The use of (R)-Binap as the chiral ligand afforded the (+) cyclized compound in 45% ee, when the (-) enantiomer was obtained with 77% ee in the presence of (S)-Binap. All the results suggest that in this case the enantioselective step is the diastereoselective protonation of the palladium-carbene intermediates. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.084
• 作为产物：
  描述：

  糠醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 作用下， 生成 1-(2-furyl)oct-2-yn-1-ol
  参考文献：
  名称：

  Moureu; Desmots, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1902, vol. 134, p. 356

  摘要：

  DOI：

文献信息

• Denisov, V. R.; Romas', A. D.; Klindukhov, V. P., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 5.2, p. 824 - 831
  作者：Denisov, V. R.、Romas', A. D.、Klindukhov, V. P.、Shustitskaya, S. E.、Alekseeva, E. M.

  DOI：——

  日期：——
• Moureu; Desmots, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1902, vol. 134, p. 356
  作者：Moureu、Desmots

  DOI：——

  日期：——
• Asymmetric palladium-catalyzed annulation of benzene-1,2-diol and racemic secondary propargylic carbonates bearing two different substituents
  作者：Norbert Dominczak、Céline Damez、Bouchra Rhers、Jean-Robert Labrosse、Paul Lhoste、Boguslaw Kryczka、Denis Sinou

  DOI：10.1016/j.tet.2005.01.084

  日期：2005.3

  The palladium-catalyzed cyclization of benzene-1,2-diol with various racemic secondary propargyl carbonates having no acetylenic hydrogen in the presence of (R)-Binap as the chiral ligand afforded the two regioisomers of the corresponding 2,3-dihydro-1,4-dioxin derivatives in quite good yields, and also in enantioselectivities going from 40 to 97%. The cyclization of benzene-1,2-diol with methyl (R)-1-methyl-3-phenylpro-2-yn-1-yl carbonate in the presence of dppb as the achiral ligand afforded 2-benzylidene-3-methyl-2,3-dihydro-1,4-benzodioxine as the major product with 15% ee. The use of (R)-Binap as the chiral ligand afforded the (+) cyclized compound in 45% ee, when the (-) enantiomer was obtained with 77% ee in the presence of (S)-Binap. All the results suggest that in this case the enantioselective step is the diastereoselective protonation of the palladium-carbene intermediates. (C) 2005 Elsevier Ltd. All rights reserved.