1-(4,5-dihydrofuran-2-yl)cyclopentanol | 129529-77-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4,5-dihydrofuran-2-yl)cyclopentanol
• 英文别名: Cyclopentanol, 1-(4,5-dihydro-2-furanyl)-；1-(2,3-dihydrofuran-5-yl)cyclopentan-1-ol
• CAS: 129529-77-7
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: CPSMHSVRWOKNNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4,5-dihydrofuran-2-yl)cyclopentanol 在 Dowex-50X 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到1-氧杂螺[4.5]癸烷-6-酮
  参考文献：
  名称：

  Paquette, Leo A.; Lawhorn, David E.; Teleha, Christopher A., Heterocycles, 1990, vol. 30, # 2, p. 765 - 769

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氢呋喃 、 环戊酮 在 叔丁基锂 作用下， 生成 1-(4,5-dihydrofuran-2-yl)cyclopentanol
  参考文献：
  名称：

  Paquette, Leo A.; Lawhorn, David E.; Teleha, Christopher A., Heterocycles, 1990, vol. 30, # 2, p. 765 - 769

  摘要：

  DOI：

文献信息

• A metal-free dyotropic-like rearrangement of 2-oxa allylic alcohols in the presence of organoboronic acids
  作者：Weimin Ye、Wenbo Li、Junliang Zhang

  DOI：10.1039/c4cc03450c

  日期：——

  An unprecedented dyotropic-like rearrangement of 2-oxa allylic alcohols in the presence of catalytic amounts of Selectfluor and DABCO was reported.

  报道了在存在催化剂量的Selectfluor和DABCO的情况下，2-氧杂烯丙醇的前所未有的双向重排。
• Catalytic intermolecular carbon electrophile induced semipinacol rearrangement
  作者：Qing-Wei Zhang、Xiao-Bo Zhang、Bao-Sheng Li、Kai Xiang、Fu-Min Zhang、Shao-Hua Wang、Yong-Qiang Tu

  DOI：10.1039/c2cc38585f

  日期：——

  A catalytic intermolecular carbon electrophile induced semipinacol rearrangement was realized and the asymmetric version was also preliminarily accomplished with 92% and 82% ee. The complex tricyclic system architecture with four continuous stereogenic centers could be achieved from simple starting materials in a single step under mild conditions.

  实现了分子间碳亲电子诱导半频哪醇重排催化反应，并初步完成了不对称版本的重排，ee值分别为92%和82%。在温和的条件下，只需一步就能从简单的起始材料制备出具有四个连续立体中心的复杂三环体系结构。
• A Facile Access to Densely Functionalized Substituted Cyclopentanes and Spiro Cyclopentanes. Carbocation Stabilization Directed Bond Migration in Rearrangement of Cyclobutanes
  作者：Azizul Haque、Anjan Ghatak、Subrata Ghosh、Nanda Ghoshal

  DOI：10.1021/jo970283m

  日期：1997.7.1
• Synthesis and molecular structure of belted spirocyclic tetrahydrofurans, a new class of preorganized hosts for cations
  作者：Leo A. Paquette、Joanna T. Negri、Robin D. Rogers

  DOI：10.1021/jo00040a041

  日期：1992.7

  The preparation and binding properties of spirocyclic tetrahydrofurans 7-11 are described. The condensation of cyclopentanone with 5-lithio-2,3-dihydrofuran (12) provided an alcohol which readily rearranged to ketone 14 under acidic conditions. ''Capping'' of the carbonyl group in 14 so as to generate a second spiro tetrahydrofuran subunit gave rise to 7 and 8. Starting with cyclobutanone, 2-fold ring expansion involving 12 provided the key reactions leading to 22 and 23, which were 'capped' as before. Crystal structure data are available for 9, 11, and 22. In addition, the variable-temperature NMR behavior of 7 and 10 was quantified by means of 2-D measurements. A detailed analysis is presented that shows the gauche effect to be of major importance in dictating the major conformation adopted by these ionophores. The binding properties of 7-11 have been assayed. Considerable variation was found, the efficiency being critically dependent upon the number of oxygen atoms, the relative stereochemistry of the C-O bonds, and the relative ease of conformational readjustment necessary to achieve proper organization around the oxophilic metal ion.
• PAQUETTE, LOP A.;LAWHORN, DAVID E.;TELEHA, CHRISTOPHER A., HETEROCYCLES., 30,(1990) N, SPEC. ISSUE , C. 765-769
  作者：PAQUETTE, LOP A.、LAWHORN, DAVID E.、TELEHA, CHRISTOPHER A.

  DOI：——

  日期：——