2-((E)-5-Iodo-pent-1-enyl)-furan | 118813-19-7

• 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: 2-((E)-5-Iodo-pent-1-enyl)-furan
• 英文别名: 2-[(E)-5-iodopent-1-enyl]furan
• CAS: 118813-19-7
• 化学式: C₉H₁₁IO
• 分子量: 262.09
• InChiKey: RNPZYIWSNNPIDF-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  13.14
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-((E)-5-Iodo-pent-1-enyl)-furan 在 sodium hydride 、 lithium diisopropyl amide 作用下， 反应 4.33h， 生成 (2Z,8E)-3-(Diethoxy-phosphoryloxy)-9-furan-2-yl-4-methyl-nona-2,8-dienoic acid methyl ester
  参考文献：
  名称：

  Intramolecular Diels–Alder reactions of vinylfurans leading to furanodecalins

  摘要：

  Thermolysis of the (2E,8Z)-9-(2-furyl)nonadienoate 25 at 290-degrees-C leads to an essentially quantitative yield of a single furanodecalin 26, whereas the corresponding (2E,8E)-isomer 34 undergoes a non-stereoselective cyclisation leading to the furanodecalins 26 and 35. (Z)-Alkenoate functions undergo partial isomerisation prior to cyclisation and so lead to mixtures of isomers. Alkyl groups can be incorporated around the reaction sites, but this can result in overwhelming competition from side reactions. The corresponding 3-furyl analogues 56 and 59 display very similar reactivities.

  DOI：

  10.1039/p19930002395
• 作为产物：
  描述：

  (E)-5-(furan-2-yl)pent-4-en-1-ol 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 2-((E)-5-Iodo-pent-1-enyl)-furan
  参考文献：
  名称：

  Intramolecular Diels–Alder reactions of vinylfurans leading to furanodecalins

  摘要：

  Thermolysis of the (2E,8Z)-9-(2-furyl)nonadienoate 25 at 290-degrees-C leads to an essentially quantitative yield of a single furanodecalin 26, whereas the corresponding (2E,8E)-isomer 34 undergoes a non-stereoselective cyclisation leading to the furanodecalins 26 and 35. (Z)-Alkenoate functions undergo partial isomerisation prior to cyclisation and so lead to mixtures of isomers. Alkyl groups can be incorporated around the reaction sites, but this can result in overwhelming competition from side reactions. The corresponding 3-furyl analogues 56 and 59 display very similar reactivities.

  DOI：

  10.1039/p19930002395

文献信息

• Furanodecalin synthesis using intramolecular Diels-Alder reactions of vinylfurans
  作者：John A Cooper、Philip Cornwall、Colin P Dell、David W Knight

  DOI：10.1016/s0040-4039(00)87847-8

  日期：——

  Intramolecular Diels-Alder cyclisations of the 2-vinylfurans (3), (9), (11) and (16) occur smoothly at 280–290°C to give the corresponding furanodecalins in 63–97% yields; the 3-substituted furans (18) and (20) behave similarly and in both series, cyclisations of the -isomers [ (3) and (18)] are stereospecific, giving only - fused furanodecalins [(4) and (19)].

  2-乙烯基呋喃的分子内Diels-Alder环化反应（3），（9），（11）和（16）在280–290°C时平稳发生，从而以63–97％的收率得到相应的呋喃十氢化萘；3-取代的呋喃（18）和（20）的行为相似，并且在两个系列中，-异构体[ （3）和（18）]的环化都是立体特异性的，仅产生-融合的呋喃十氢化萘[[4]和（19）]。 。
• COOPER, JOHN A.;CORNWALL, PHILIP;DELL, COLIN P.;KNIGHT, DAVID W., TETRAHEDRON LETT., 29,(1988) N 17, 2107-2110
  作者：COOPER, JOHN A.、CORNWALL, PHILIP、DELL, COLIN P.、KNIGHT, DAVID W.

  DOI：——

  日期：——
• Intramolecular Diels–Alder reactions of vinylfurans leading to furanodecalins
  作者：Philip Cornwall、Colin P. Dell、David W. Knight

  DOI：10.1039/p19930002395

  日期：——

  Thermolysis of the (2E,8Z)-9-(2-furyl)nonadienoate 25 at 290-degrees-C leads to an essentially quantitative yield of a single furanodecalin 26, whereas the corresponding (2E,8E)-isomer 34 undergoes a non-stereoselective cyclisation leading to the furanodecalins 26 and 35. (Z)-Alkenoate functions undergo partial isomerisation prior to cyclisation and so lead to mixtures of isomers. Alkyl groups can be incorporated around the reaction sites, but this can result in overwhelming competition from side reactions. The corresponding 3-furyl analogues 56 and 59 display very similar reactivities.