6-(2-furyl)-1-hexyne | 122132-28-9

• 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: 6-(2-furyl)-1-hexyne
• 英文别名: 2-(hex-5-ynyl)furan；2-hex-5-ynyl-furan；2-Hex-5-ynylfuran
• CAS: 122132-28-9
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: YVHZLXYABQLNCG-UHFFFAOYSA-N

物化性质

• 沸点：
  215.2±23.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  6-(2-furyl)-1-hexyne 在 manganese(IV) oxide 、 正丁基锂 、 cerium(III) chloride 、 乙醚 、 红铝 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 20.0 ℃ 、1899.99 MPa 条件下， 反应 24.0h， 生成
  参考文献：
  名称：

  呋喃的高压介导的分子内Diels-Alder反应：控制单加双亲亲烯物的环加成的因素。

  摘要：

  已经研究了具有2-烷基取代基和末端α，β-不饱和酮的呋喃的分子内Diels-Alder反应。据报道，改变环加成反应的简便性和立体化学后，改变呋喃的取代度，桥链长度以及亲二烯体上活化基团的位置的后果。

  DOI：

  10.1016/s0040-4039(00)80668-1
• 作为产物：
  描述：

  8-furan-2-yl-2-methyl-oct-3-yn-2-ol 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以58%的产率得到6-(2-furyl)-1-hexyne
  参考文献：
  名称：

  Synthesis of Natural Polyacetylenes Bearing Furan Rings

  摘要：

  The first total syntheses of four new polyacetylene compounds have been achieved using convergent routes, which involved Cadiot-Chodkiewicz copper-catalyzed cross-coupling reactions to sp-sp centers as the key steps. 19-Furan-2-ylnonadeca-5,7-diynoic acid (1), 19-furan-2-ylnonadeca-5,7-diynoic acid methyl ester (2), 2-pentacosa-7,9-diynylfuran (3), and 21-furan-2-ylhenicosa-14,16-diyn-1-ol (4) were stable and could be readily identified, isolated, and purified in high overall yields.

  DOI：

  10.1021/np9000637

文献信息

• Gold(I)-Catalyzed Intramolecular [4+3]-Cycloaddition Reactions with Furan Propargyl Esters as the Substrates: Carbenoid vs. Stabilized Allyl Cation
  作者：Benjamin Gung、Ryan Conyers、Josh Wonser

  DOI：10.1055/s-0033-1338946

  日期：——

  The tricyclic ring system with an oxabicyclo[3.2.1]octadiene and a fused six-membered ring was produced efficiently using the readily available propargyl ester furan substrate in the presence of a Au(I) complex. The reaction involves a tandem 3,3-rearrangement of the propargyl ester followed by an intramolecular [4+3]-cycloaddition reaction. Both the primary ligand of the gold complex (N-heterocyclic

  在 Au(I) 配合物的存在下，使用容易获得的炔丙酯呋喃底物有效地生产了具有氧杂双环 [3.2.1] 辛二烯和稠合六元环的三环系统。该反应包括炔丙酯的串联 3,3-重排，然后是分子内 [4+3]-环加成反应。金配合物的主要配体 (N-杂环卡宾; NHC) 和中性动态配体 (PhCN) 对反应的成功都很重要。
• Amino Acid Derived Enamides:  Synthesis and Aminopeptidase Activity
  作者：Richard R. Cesati、Greg Dwyer、Reinaldo C. Jones、Megan P. Hayes、Padmaja Yalamanchili、David S. Casebier

  DOI：10.1021/ol7025729

  日期：2007.12.1

  Recently developed copper-catalyzed coupling methodology has been applied to the Synthesis of amino acid derived enamides. Bond formation proved to be strongly influenced by protection strategy and vinyl iodide substitution while tolerant of limited side chain functionality. Assessment of aminopeptidase activity revealed a preference for (E)-1,2-disubstituted constructs.
• A Domino Diels–Alder Approach toward the Tetracyclic Nicandrenone Framework
  作者：Emily G. Mackay、Marck Nörret、Leon S.-M. Wong、Ignace Louis、Andrew L. Lawrence、Anthony C. Willis、Michael S. Sherburn

  DOI：10.1021/acs.orglett.5b02412

  日期：2015.11.20

  The tetracarbocyclic framework of the nicandrenone natural products is formed in one step from a linear precursor via a domino intramolecular Diels-Alder/intramolecular furan Diels-Alder/aromatization sequence. The approach represents a new 0 -> ABCD strategy for the preparation of aromatic steroids.
• Rhodium carbenoid mediated cyclizations of o-alkynyl-substituted .alpha.-diazoacetophenones
  作者：Albert Padwa、Keith E. Krumpe、Jamal M. Kassir

  DOI：10.1021/jo00044a032

  日期：1992.8

  o-Alkynyl-substituted alpha-diazoacetophenones undergo facile cyclization to indenone derivatives upon treatment with catalytic quantities of Rh(II) carboxylates. A variety of structural influences were encountered by varying the nature of the substituent group attached to the alkyne carbon atom. The cyclization reaction involves addition of a rhodium stabilized carbenoid onto the acetylenic pi-bond to generate a vinyl carbenoid. The vinyl carbenoid was found to undergo both CH and CC migration as well as delta-CH insertion into the alkyl backbone. Different catalysts were shown to result in significant variation in the product ratios for these reactions. Treatment of o-(5-(allyloxy)-1-pentynyl)-alpha-diazoacetophenone with rhodium(II) mandelate afforded 2-(2-propen-1-yl)-2-(1-oxo-1H-indenyl)-2,3,4,5-tetrahydrofuran in high yield. The formation of this compound involves initial formation of a vinyl carbenoid which reacts with the neighboring oxygen atom to give an oxonium ylide which subsequently undergoes a 2,3-sigmatropic rearrangement. When 2-ethynyl-alpha-diazoacetophenone is used, only products derived from 6-endo closure are observed. Substituted o-alkynyl alpha-diazoacetophenones give products derived from 5-exo cyclization. The mode of ring closure is controlled by both steric and electronic factors.
• HARWOOD, LAURENCE M.;LEEMING, SARAH A.;ISAACS, NEIL S.;JONES, GERAINT;PIC+, TETRAHEDRON LETT., 29,(1988) N 39, C. 5017-5020
  作者：HARWOOD, LAURENCE M.、LEEMING, SARAH A.、ISAACS, NEIL S.、JONES, GERAINT、PIC+

  DOI：——

  日期：——