3-(2-Furanyl)iodobutane | 169892-44-8

• 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)iodobutane
• 英文别名: 2-(4-Iodobutan-2-yl)furan
• CAS: 169892-44-8
• 化学式: C₈H₁₁IO
• 分子量: 250.079
• InChiKey: FSVZDSKSLDJQFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-Furanyl)iodobutane 在 sodium hydroxide 、 硫酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 5.25h， 生成 6-(2-Furanyl)-3-heptanone
  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)butan-1-ol 在 吡啶 、 sodium iodide 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 48.0h， 生成 3-(2-Furanyl)iodobutane
  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

• 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。
• Intramolecular 4 + 3 Cycloadditions. Further Studies of (Trimethylsilyl)methyl Allylic Sulfones
  作者：Michael Harmata、Barry F. Herron、Mehmet Kahraman、Charles. L. Barnes

  DOI：10.1021/jo970511c

  日期：1997.8.1