3-(2-Furanyl)butan-1-ol | 169892-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(2-Furanyl)butan-1-ol
• 英文别名: 3-(Furan-2-yl)butan-1-ol
• CAS: 169892-42-6
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: IZAOMISSXRELOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 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：

  3-(2-Furanyl)butan-1-ol 在 吡啶 、 sodium hydroxide 、 硫酸 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 氯仿 、 丙酮 为溶剂， 反应 67.25h， 生成 3-Ethynyl-6-(2-furanyl)-3-heptanol
  参考文献：
  名称：

  Intramolecular [4+3] Cycloadditions. Studies of Relative Asymmetric Induction

  摘要：

  Treatment df both the E and Z isomers of alkoxyallylic sulfones 20a and 20b with TiCl4 results in the formation of 4 + 3 cycloadducts by intramolecular cycloaddition. The distribution of diastereomers is different from each isomer of educt. This suggests that cycloaddition occurs faster than any isomerization process of the intermediate allylic cations. Both the E and Z isomers of 20c lead to the same 4 + 3 cycloadduct with essentially complete diastereoselectivity. Inherently high simple diastereoselection and a strong conformational bias in the allylic cation intermediates for both isomers account for this selectivity. The importance of allylic cation stereochemistry in these reactions is underscored by the cyclization of 20d. The Z isomer give only 4 + 3 cycloadducts with excellent relative but poor simple diastereoselection, suggestive of a concerted reaction. The E isomer give a [3 + 2] cycloadduct, enol ether 60, as the major cycloadduct as well as 4 + 3 cycloadducts and chloride-trapping product 61. This result is indicative of a stepwise reaction. The data reflect the importance of allylic cation stereochemistry in the regiochemical and stereochemical outcomes of intramolecular 4 + 3 cycloaddition reactions.

  DOI：

  10.1021/jo00121a028
• 作为产物：
  描述：

  3-(2-Furanyl)butyric acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到3-(2-Furanyl)butan-1-ol
  参考文献：
  名称：

  Intramolecular [4+3] Cycloadditions. Studies of Relative Asymmetric Induction

  摘要：

  Treatment df both the E and Z isomers of alkoxyallylic sulfones 20a and 20b with TiCl4 results in the formation of 4 + 3 cycloadducts by intramolecular cycloaddition. The distribution of diastereomers is different from each isomer of educt. This suggests that cycloaddition occurs faster than any isomerization process of the intermediate allylic cations. Both the E and Z isomers of 20c lead to the same 4 + 3 cycloadduct with essentially complete diastereoselectivity. Inherently high simple diastereoselection and a strong conformational bias in the allylic cation intermediates for both isomers account for this selectivity. The importance of allylic cation stereochemistry in these reactions is underscored by the cyclization of 20d. The Z isomer give only 4 + 3 cycloadducts with excellent relative but poor simple diastereoselection, suggestive of a concerted reaction. The E isomer give a [3 + 2] cycloadduct, enol ether 60, as the major cycloadduct as well as 4 + 3 cycloadducts and chloride-trapping product 61. This result is indicative of a stepwise reaction. The data reflect the importance of allylic cation stereochemistry in the regiochemical and stereochemical outcomes of intramolecular 4 + 3 cycloaddition reactions.

  DOI：

  10.1021/jo00121a028

文献信息

• Rapid and Stereoselective Synthesis of Spirocyclic Ethers via the Intramolecular Piancatelli Rearrangement
  作者：Leoni I. Palmer、Javier Read de Alaniz

  DOI：10.1021/ol303263q

  日期：2013.2.1

  The first example of a Piancatelli rearrangement of alcohols is demonstrated utilizing dysprosium(III) triflate as a catalyst to access oxaspirocycles in a highly diastereoselective manner. The cascade reaction constructs the spirocyclic ether ring system and the tertiary stereocenter in a single operation and is experimentally easy to perform.

  利用三氟甲磺酸（III）作为催化剂以高度非对映选择性的方式进入氧杂螺环，证明了醇的片卡特凯利重排的第一个例子。级联反应可在一次操作中构建螺环醚环系统和叔立体中心，并且在实验上易于实现。
• Synthesis and in vitro antimalarial activity of spiro-analogues of peroxyplakoric acids
  作者：Yun Li、Qi Zhang、Sergio Wittlin、Hong-Xia Jin、Yikang Wu

  DOI：10.1016/j.tet.2009.06.050

  日期：2009.8

  1,6,7-trioxa-spiro[4.5]decanes were synthesized using the hydrogen peroxide in UHP (urea–H2O2 complex) as the source of the peroxy bond. Incorporation of H2O2 into the organic molecular framework was facilitated by the potential to form a five- or six memberd cyclic hemiketal. Saturation of the double bond in a substituted γ-keto-butenal, a step required in all the syntheses, was achieved in one case

  使用过氧化氢在UHP（尿素-H 2 O 2络合物）中合成了四个1,2,7-三氧杂螺[5.5]十一烷和两个1,6,7-三氧杂螺[4.5]癸烷。过氧键。通过形成五元或六元环状半缩酮的潜力，可以促进将H 2 O 2引入有机分子骨架中。在一种情况下，用NaI /浓盐酸在低温下实现了取代的γ-酮-丁醛中双键的饱和，这是所有合成所需要的步骤，而在室温下未裂解TBS保护基或引起过多的副反应。温度。所有这些过氧化物均显示出与天然过氧苯甲酸和已知类似物相当的体外抗疟活性。
• Multiphotocatalyst Cascades: From Furans to Fused Butyrolactones and Substituted Cyclopentanones
  作者：Lamprini-Panagiota Apostolina、Artemis Bosveli、Antonia Profyllidou、Tamsyn Montagnon、Vasileios Tsopanakis、Maria Kaloumenou、Dimitris Kalaitzakis、Georgios Vassilikogiannakis

  DOI：10.1021/acs.orglett.2c03513

  日期：2022.12.9

  relies on a new and mild method for butenolide synthesis mediated by thiols. The initial photooxygenation and butenolide synthesis have been merged with subsequent photoredox reactions to achieve rare dual-photocatalyst cascades affording various fused butyrolactones. Ground state Lewis acid activity for methylene blue has been unveiled and then exploited in the synthesis of substituted cyclopentanones

  高价值的含氧多环化合物已经通过一锅法从简单的前体快速有效地获得。报告的方法依赖于一种新的温和方法，用于由硫醇介导的丁烯内酯合成。最初的光氧化和丁烯内酯合成已与随后的光氧化还原反应合并，以实现罕见的双光催化剂级联，提供各种稠合丁内酯。亚甲基蓝的基态路易斯酸活性已被揭示，然后被用于合成取代的环戊酮。
• Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates
  作者：Michael E. Jung、Mehrak Kiankarimi

  DOI：10.1021/jo9721554

  日期：1998.5.1

  The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.
• Intramolecular [4+3] Cycloadditions. Studies of Relative Asymmetric Induction
  作者：Michael Harmata、Chandra B. Gamlath、Charles L. Barnes、Darin E. Jones

  DOI：10.1021/jo00121a028

  日期：1995.8

  Treatment df both the E and Z isomers of alkoxyallylic sulfones 20a and 20b with TiCl4 results in the formation of 4 + 3 cycloadducts by intramolecular cycloaddition. The distribution of diastereomers is different from each isomer of educt. This suggests that cycloaddition occurs faster than any isomerization process of the intermediate allylic cations. Both the E and Z isomers of 20c lead to the same 4 + 3 cycloadduct with essentially complete diastereoselectivity. Inherently high simple diastereoselection and a strong conformational bias in the allylic cation intermediates for both isomers account for this selectivity. The importance of allylic cation stereochemistry in these reactions is underscored by the cyclization of 20d. The Z isomer give only 4 + 3 cycloadducts with excellent relative but poor simple diastereoselection, suggestive of a concerted reaction. The E isomer give a [3 + 2] cycloadduct, enol ether 60, as the major cycloadduct as well as 4 + 3 cycloadducts and chloride-trapping product 61. This result is indicative of a stepwise reaction. The data reflect the importance of allylic cation stereochemistry in the regiochemical and stereochemical outcomes of intramolecular 4 + 3 cycloaddition reactions.