1-(4,5-dihydro-6-furyl)cyclobutanol | 134179-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 1-(4,5-dihydro-6-furyl)cyclobutanol
• 英文别名: 1-(4,5-dihydrofuran-2-yl)cyclobutanol；1-(2,3-Dihydrofuran-5-yl)cyclobutan-1-ol
• CAS: 134179-00-3
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: SFRYRBFXUUAXQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  248.0±39.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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-dihydro-6-furyl)cyclobutanol 在 Dowex-50X₄-400 、 叔丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (5R,6S)-1,7-Dioxa-dispiro[4.0.4.4]tetradecan-11-one
  参考文献：
  名称：

  Synthesis and molecular structure of belted spirocyclic tetrahydrofurans, a new class of preorganized hosts for cations

  摘要：

  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.

  DOI：

  10.1021/jo00040a041
• 作为产物：
  描述：

  环丁酮 、 5-lithio-2,3-dihydrofuran 以 四氢呋喃 为溶剂， 以83%的产率得到1-(4,5-dihydro-6-furyl)cyclobutanol
  参考文献：
  名称：

  Negri, Joanna T.; Rogers, Robin D.; Paquette, Leo A., Journal of the American Chemical Society, 1991, vol. 113, # 13, p. 5073 - 5075

  摘要：

  DOI：

文献信息

• 1-Oxaspiro[4.4]nonan-6-ones. Synthetic Access via Oxonium Ion Technology, Optical Resolution, and Conversion into Enantiopure Spirocyclic α,β-Butenolides
  作者：Leo A. Paquette、Dafydd R. Owen、Richard Todd Bibart、Christopher K. Seekamp、Alexandra L. Kahane、James C. Lanter、Miriam Alvarez Corral

  DOI：10.1021/jo010026o

  日期：2001.4.1

  A general approach to the synthesis of enantiomerically pure spirocyclic alpha,beta-butenolides is presented where the fundamental framework is rapidly elaborated by acid- or bromonium ion-induced rearrangement of the carbinol derived by addition of 2-lithio-4,5-dihydrofuran to cyclobutanone. Subsequent resolution of the resulting ketones by either sulfoximine or mandelate acetal technology has been

  提出了合成对映体纯的螺环α，β-丁烯内酯的一般方法，其中基本构架通过酸或溴离子诱导的甲醇的重排反应而迅速完善，该重排反应是通过向2-硫代-4,5-二氢呋喃中添加而得到的。环丁酮。通过硫代亚胺或扁桃酸缩醛技术对所得酮的后续拆分已得到有效应用。这些结构单元的可获得性又使得获得以17、35和38为代表的二氢呋喃的对映异构体以及诸如25和31的内酯以及目标标题化合物成为可能。早期中间体的互补还原提供了额外的优势，即可以按需获得α-和β-立体异构甲醇系列。
• Brønsted Acid Catalyzed Enantioselective Semipinacol Rearrangement for the Synthesis of Chiral Spiroethers
  作者：Qing-Wei Zhang、Chun-An Fan、Hai-Jun Zhang、Yong-Qiang Tu、Yu-Ming Zhao、Peiming Gu、Zhi-Min Chen

  DOI：10.1002/anie.200904565

  日期：2009.10.26

  A new twist: The catalytic asymmetric semipinacol rearrangement reaction of 2‐oxo allylic alcohols 1 in the presence of a catalytic amount of chiral phosphoric acid (R)‐2 a or its silver salt (R)‐2 b affords enantiomerically pure spiroethers 3.

  一个新的转折：2-氧代烯丙醇的催化不对称semipinacol重排反应1在手性磷酸（催化量存在- [R ）- 2或它的银盐（[R ）- 2 B，得到对映体纯spiroethers 3。
• 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。
• NEGRI, JOANNA T.;ROGERS, ROBIN D.;PAQUETTE, LEO A., J. AMER. CHEM. SOC., 113,(1991) N3, C. 5073-5075
  作者：NEGRI, JOANNA T.、ROGERS, ROBIN D.、PAQUETTE, LEO A.

  DOI：——

  日期：——