(Z)-3-(2-penten-4-ynyl)furan | 187335-12-2

• 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: (Z)-3-(2-penten-4-ynyl)furan
• 英文别名: 3-[(Z)-pent-2-en-4-ynyl]furan
• CAS: 187335-12-2
• 化学式: C₉H₈O
• 分子量: 132.162
• InChiKey: PKEABQYBEHLHMC-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  (Z)-3-(2-penten-4-ynyl)furan 在 碘 、 copper(l) cyanide 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-((2Z,4E)-5-Iodo-4-methyl-penta-2,4-dienyl)-furan
  参考文献：
  名称：

  通过在共轭末端烯中添加 MeMgSnBu3 立体选择性合成 2-取代的 1-IODO-1,3-二烯；(2E,4Z,6E)-去氢松松素的立体控制合成

  摘要：

  Addition of MeMgSnBu3 to the conjugated enynes 1 and 5 were thoroughly studied. The addition reactions were proceeded stereoselectively at -20 degrees C, but a thermal isomerization occurred when the reaction was carried out at 0 degrees C. (2E,4Z,6E)-Dehydrodendrolasin 8 was synthesized using the isomerized 2-methyl-1-iodo-1,3-diene product 13.

  DOI：

  10.3987/com-12-s(n)84
• 作为产物：
  描述：

  3-furylacetaldehyde 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三正丁基氢锡 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 1.17h， 生成 (Z)-3-(2-penten-4-ynyl)furan
  参考文献：
  名称：

  Stereocontrolled synthesis of dehydrodendrolasin: Unstable polyene furanosesquiterpenoids

  摘要：

  Marine furanosesquiterpenoids, (2E,4E,6E)- and (2Z,4E,6E)-dehydrodendrolasin (2) and (3), were synthesized in a geometrically controlled fashion. For the synthesis of 2, stereospecific addition of methyl(tributylstannyl)magnesium to E-enyne was employed effectively to afford (2E,4E)-3-(5-iodo-4-methyl-2,4-pentadienyl)furan (15). For the synthesis of 3, the key geometrical control for Z-enyne intermediate (7) was performed by a Pd catalyzed stereospecific hydrogenolysis of 3-(3-furyl)-1,1-dibromopropene (16) and successive Sonogashira coupling with trimethylsilylacetylene to give (2)-3-(5-trimethylsilyl-2-penten-4-ynyl)furan (18) in one pot. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01190-8

文献信息

• STEREOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 1-IODO-1,3-dIENES BY THE ADDITION OF MeMgSnBu3 TO THE CONJUGATED TERMINAL ENYNES; STEREOCONTROLLED SYNTHESIS OF (2E,4Z,6E)-DEHYDRODENDROLASIN
  作者：Jun'ichi Uenishi、Reiko Kawahama

  DOI：10.3987/com-12-s(n)84

  日期：——

  Addition of MeMgSnBu3 to the conjugated enynes 1 and 5 were thoroughly studied. The addition reactions were proceeded stereoselectively at -20 degrees C, but a thermal isomerization occurred when the reaction was carried out at 0 degrees C. (2E,4Z,6E)-Dehydrodendrolasin 8 was synthesized using the isomerized 2-methyl-1-iodo-1,3-diene product 13.
• Stereocontrolled synthesis of dehydrodendrolasin: Unstable polyene furanosesquiterpenoids
  作者：Jun'ichi Uenishi、Reiko Kawahama、Arifumi Tanio、Shoji Wakabayashi、Osamu Yonemitsu

  DOI：10.1016/s0040-4020(96)01190-8

  日期：1997.2

  Marine furanosesquiterpenoids, (2E,4E,6E)- and (2Z,4E,6E)-dehydrodendrolasin (2) and (3), were synthesized in a geometrically controlled fashion. For the synthesis of 2, stereospecific addition of methyl(tributylstannyl)magnesium to E-enyne was employed effectively to afford (2E,4E)-3-(5-iodo-4-methyl-2,4-pentadienyl)furan (15). For the synthesis of 3, the key geometrical control for Z-enyne intermediate (7) was performed by a Pd catalyzed stereospecific hydrogenolysis of 3-(3-furyl)-1,1-dibromopropene (16) and successive Sonogashira coupling with trimethylsilylacetylene to give (2)-3-(5-trimethylsilyl-2-penten-4-ynyl)furan (18) in one pot. (C) 1997, Elsevier Science Ltd.